Merge pull request 'feat: journal closeout for profile observations + LLM tool-use fixes' (#49) from dev into main

CI surfaced three issues:
- 'famous supply project' didn't substring-match 'Famous-Supply Work topics'
  because the trailing filler word 'project' blocked the substring tier.
  Strip {project, projects} from the query before the substring check.
- SequenceMatcher fallback against `combined` (title + description +
  summary) diluted ratios to ~0.5 for plausible matches. Use title
  directly; the 0.70 tier already handles description/summary mentions.
- Test patches used patch.object on a consumer module where
  list_projects is imported locally — patch the source module instead.

Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>

.remember/tmp/save-session.pid

@@ -1 +1 @@
-2298268
+3158517

alembic/versions/0043_event_duration_replaces_end_dt.py

@@ -0,0 +1,73 @@
+"""replace events.end_dt with duration_minutes (Fable #160)
+
+Revision ID: 0043
+Revises: 0042
+Create Date: 2026-04-29
+
+Structural fix for the "end before start" bug class observed on prod
+2026-04-29: an event landed with end_dt 32 days before start_dt due
+to a tool-call mishap, then disappeared from upcoming-list filters.
+Storing duration instead of end_dt makes the invalid state
+inexpressible at the schema level (duration_minutes >= 0).
+
+Backfill rules:
+  - end_dt valid (end_dt > start_dt) → duration_minutes = total minutes
+  - end_dt == start_dt → duration_minutes = 0 (zero-duration point)
+  - end_dt NULL OR end_dt < start_dt → duration_minutes = NULL (corrupt
+    or open-ended; treated as a point event from here on)
+
+Existing API consumers continue to receive `end_dt` in responses — the
+field is now derived from `start_dt + duration_minutes` in
+``Event.to_dict()`` rather than stored.
+"""
+from alembic import op
+import sqlalchemy as sa
+
+
+revision = "0043"
+down_revision = "0042"
+branch_labels = None
+depends_on = None
+
+
+def upgrade() -> None:
+    op.add_column(
+        "events",
+        sa.Column("duration_minutes", sa.Integer(), nullable=True),
+    )
+    op.create_check_constraint(
+        "events_duration_minutes_non_negative",
+        "events",
+        "duration_minutes IS NULL OR duration_minutes >= 0",
+    )
+    # Backfill: convert valid end_dt into a minute count; leave NULL for
+    # corrupt or absent end_dt. Bad rows (end_dt <= start_dt) collapse
+    # cleanly to point events instead of forcing a recovery guess.
+    op.execute(
+        """
+        UPDATE events
+        SET duration_minutes = CAST(
+            EXTRACT(EPOCH FROM (end_dt - start_dt)) / 60 AS INTEGER
+        )
+        WHERE end_dt IS NOT NULL AND end_dt >= start_dt
+        """
+    )
+    op.drop_column("events", "end_dt")
+
+
+def downgrade() -> None:
+    op.add_column(
+        "events",
+        sa.Column("end_dt", sa.DateTime(timezone=True), nullable=True),
+    )
+    # Restore end_dt = start_dt + duration_minutes minutes for rows that
+    # had a duration. NULL duration → NULL end_dt (point event).
+    op.execute(
+        """
+        UPDATE events
+        SET end_dt = start_dt + (duration_minutes || ' minutes')::interval
+        WHERE duration_minutes IS NOT NULL
+        """
+    )
+    op.drop_constraint("events_duration_minutes_non_negative", "events")
+    op.drop_column("events", "duration_minutes")

docs/design-system.md

@@ -568,6 +568,17 @@ Items deliberately not addressed in this round; revisit when a real need surface
 - Standalone voice/tone audit across every UI string — opportunistic-only; full sweep deferred unless drift becomes visible.
 - A handful of editor utility buttons (`.btn-suggest-tags`, `.btn-link-all`, AI assist generate/proofread/accept/reject set, etc.) — currently ghost-styled and visually compliant; revisited only if they read off in practice.
 
+### Flutter app port — shipped 2026-04-28
+
+The companion mobile app (`fabled_app` / FabledApp repo) tracks the same design system. Two commits:
+
+- **Foundation port** — `0f05f47`. `lib/core/theme.dart` rewritten with the Obsidian/Iron/Pewter dark palette, warm parchment light palette, dusty violet `#5B4A8A` primary. Inter loaded for body, JetBrains Mono available at call sites, Fraunces for headlines ≥18px. New `ActionColors` ThemeExtension exposes Moss/Bronze/Oxblood/Pewter outside the `ColorScheme` (Material's primary/secondary/tertiary slots all carry brand accent, so action tokens need their own home). `GradientButton` recolored to dusty-violet gradient.
+- **Surface phase** — `b9e68e3`. `lucide_icons ^0.257.0` installed; 107 `Icons.*` references across 21 files swapped to `LucideIcons.*`. Input border radius 24 → 8 in both themes. ChatMessageBubble Illuminated Transcript fixes — neutral border on user bubbles, `surface`/Iron bg on assistant bubbles, asymmetric corner restoration (only bottom-left clipped, not both left corners), accent-tinted glow shadow added. 5 destructive confirm buttons across notes / tasks / chat / calendar wired to `ActionColors.destructive`. Calendar event Save wired to `ActionColors.primary` as the reference Moss site. 4 hardcoded indigo Color literals → dusty-violet equivalents.
+
+The Flutter port doesn't decompose into 7 PRs the way web did because Flutter's centralized `theme.dart` means most palette/font work happens in one file. Per-screen Save / Cancel reclassification beyond the calendar event Save is opportunistic — the wiring pattern (`Theme.of(context).extension<ActionColors>()!.primary`) is established and applied incrementally as files are touched.
+
+Pattern reference for downstream screens: see `lib/screens/calendar/event_form_sheet.dart` for `ActionColors.primary` usage on Save buttons; see the dialog spots in `note_edit_screen.dart` / `task_edit_screen.dart` / `note_detail_screen.dart` / `conversations_tab_screen.dart` for `ActionColors.destructive` on confirm-Delete buttons.
+
 ### Open threads
 
 *New threads will accumulate here as gaps surface in real use.*

fable-mcp/pyproject.toml

@@ -4,7 +4,7 @@ build-backend = "hatchling.build"
 
 [project]
 name = "fable-mcp"
-version = "0.2.6"
+version = "0.3.0"
 description = "MCP server for Fabled Scribe"
 requires-python = ">=3.12"
 dependencies = [

fable-mcp/uv.lock

@@ -184,7 +184,7 @@ wheels = [
 
 [[package]]
 name = "fable-mcp"
-version = "0.2.6"
+version = "0.3.0"
 source = { editable = "." }
 dependencies = [
     { name = "httpx" },

frontend/src/api/client.ts

@@ -317,6 +317,7 @@ export interface JournalConfig {
   day_rollover_hour: number;
   morning_end_hour?: number;
   midday_end_hour?: number;
+  closeout_enabled?: boolean;
   // Ambient-context fields (carried forward from the briefing config schema)
   locations?: { home?: JournalLocation; work?: JournalLocation };
   temp_unit?: 'C' | 'F';
@@ -545,7 +546,7 @@ export interface EventUpdatePayload {
   description?: string;
   location?: string;
   color?: string;
-  recurrence?: string;
+  recurrence?: string | null;
   project_id?: number;
 }
 
@@ -696,3 +697,11 @@ export const updateProfile = (data: Partial<UserProfile>) =>
 export const consolidateProfile = () =>
   apiPost<{ status: string; learned_summary: string }>('/api/profile/consolidate', {})
 export const clearProfileObservations = () => apiDelete('/api/profile/observations')
+
+export interface ProfileObservationEntry {
+  date: string
+  bullets: string
+}
+
+export const listProfileObservations = () =>
+  apiGet<{ observations: ProfileObservationEntry[] }>('/api/profile/observations')

frontend/src/components/EventSlideOver.vue

@@ -1,5 +1,5 @@
 <script setup lang="ts">
-import { X } from "lucide-vue-next";
+import { Trash2, X } from "lucide-vue-next";
 import { ref, computed, watch, onMounted, onUnmounted } from "vue";
 import { createEvent, updateEvent, deleteEvent, type EventEntry, type EventCreatePayload, type EventUpdatePayload } from "@/api/client";
 import ProjectSelector from "@/components/ProjectSelector.vue";
@@ -37,6 +37,36 @@ const description = ref("");
 const location = ref("");
 const color = ref("");
 const projectId = ref<number | null>(null);
+const recurrence = ref<string>("");
+
+// Preset RRULE strings. The select binds to `recurrencePreset`, which writes
+// through to `recurrence`. CalDAV-imported rules with extra parts
+// (e.g. `FREQ=WEEKLY;BYDAY=MO,WE,FR`) fall through to "custom" and the raw
+// string is shown read-only below the select.
+const RECURRENCE_PRESETS: Record<string, string> = {
+  none: "",
+  daily: "FREQ=DAILY",
+  weekly: "FREQ=WEEKLY",
+  monthly: "FREQ=MONTHLY",
+  yearly: "FREQ=YEARLY",
+};
+
+const recurrencePreset = computed<string>({
+  get() {
+    const r = (recurrence.value || "").trim();
+    if (!r) return "none";
+    for (const [key, val] of Object.entries(RECURRENCE_PRESETS)) {
+      if (val && val === r) return key;
+    }
+    return "custom";
+  },
+  set(key: string) {
+    if (key === "custom") return; // no-op; can't pick custom from dropdown
+    recurrence.value = RECURRENCE_PRESETS[key] ?? "";
+  },
+});
+
+const isCustomRecurrence = computed(() => recurrencePreset.value === "custom");
 
 function dateFromIso(iso: string): string {
   const d = new Date(iso);
@@ -115,6 +145,7 @@ function resetForm() {
     location.value = props.event.location || "";
     color.value = props.event.color || "";
     projectId.value = props.event.project_id;
+    recurrence.value = props.event.recurrence || "";
     _lastDurationMin = !allDay.value && startTime.value && endTime.value ? durationMin(startTime.value, endTime.value) : 60;
     if (_lastDurationMin <= 0) _lastDurationMin = 60;
   } else {
@@ -130,6 +161,7 @@ function resetForm() {
     location.value = "";
     color.value = "";
     projectId.value = null;
+    recurrence.value = "";
     _lastDurationMin = 60;
   }
   deleteConfirm.value = false;
@@ -177,26 +209,69 @@ watch(() => props.event, resetForm, { immediate: true });
 watch(() => props.initialDate, resetForm);
 
 function handleKeydown(e: KeyboardEvent) {
-  if (e.key === "Escape") emit("close");
+  if (e.key === "Escape") {
+    if (deleteConfirm.value) {
+      // Esc cancels the delete-confirm rather than closing the modal —
+      // gives the user a clear way out of the destructive prompt.
+      deleteConfirm.value = false;
+      return;
+    }
+    attemptClose();
+  }
 }
 
 onMounted(() => document.addEventListener("keydown", handleKeydown));
 onUnmounted(() => document.removeEventListener("keydown", handleKeydown));
 
-async function save() {
+// ── Close / save flow ─────────────────────────────────────────────────────────
+//
+// All exit paths (X button, Esc, backdrop click) funnel through `attemptClose`.
+// The Save button is gone — explicit-commit is replaced with auto-save-on-close.
+//
+// Validity-aware behavior:
+//   - Form valid → save (PATCH for edit, POST for create), then close.
+//   - Form invalid in EDIT mode → discard the in-memory change and close.
+//     A toast tells the user what happened so they don't think their edit
+//     silently landed.
+//   - Form invalid in CREATE mode → close silently (nothing existed to begin
+//     with; no need to call this out).
+
+function isFormValid(): { valid: boolean; reason?: string } {
   if (!title.value.trim()) {
-    toast.show("Title is required", "error");
-    return;
+    return { valid: false, reason: "Title required" };
   }
   if (!startDate.value) {
-    toast.show("Start date is required", "error");
-    return;
+    return { valid: false, reason: "Start date required" };
   }
   if (!allDay.value && !startTime.value) {
-    toast.show("Start time is required", "error");
-    return;
+    return { valid: false, reason: "Start time required" };
   }
+  return { valid: true };
+}
 
+let _closing = false;
+
+async function attemptClose() {
+  if (_closing) return;
+  _closing = true;
+  try {
+    const validity = isFormValid();
+    if (!validity.valid) {
+      if (isEditMode.value) {
+        toast.show(`${validity.reason} — change discarded`, "warning");
+      }
+      // Create mode + invalid: silent close. Nothing was committed.
+      emit("close");
+      return;
+    }
+    await save();
+    emit("close");
+  } finally {
+    _closing = false;
+  }
+}
+
+async function save() {
   const start_dt = allDay.value ? `${startDate.value}T00:00:00` : toIso(startDate.value, startTime.value);
   const end_dt = endDate.value
     ? (allDay.value ? `${endDate.value}T00:00:00` : toIso(endDate.value, endTime.value))
@@ -214,9 +289,9 @@ async function save() {
         location: location.value,
         color: color.value,
         project_id: projectId.value ?? undefined,
+        recurrence: recurrence.value || null,
       };
       const updated = await updateEvent(props.event.id, payload);
-      toast.show("Event updated", "success");
       emit("updated", updated);
     } else {
       const payload: EventCreatePayload = {
@@ -228,9 +303,9 @@ async function save() {
         location: location.value,
         color: color.value,
         project_id: projectId.value ?? undefined,
+        recurrence: recurrence.value || undefined,
       };
       const created = await createEvent(payload);
-      toast.show("Event created", "success");
       emit("created", created);
     }
   } catch {
@@ -256,23 +331,57 @@ async function doDelete() {
 
 <template>
   <Teleport to="body">
-    <div class="slide-over-backdrop" @click.self="emit('close')">
-      <div class="slide-over-panel" role="dialog" aria-modal="true">
-        <div class="so-header">
-          <h2 class="so-title">{{ isEditMode ? "Edit Event" : "New Event" }}</h2>
-          <button class="so-close" @click="emit('close')" aria-label="Close"><X :size="16" /></button>
+    <div class="modal-backdrop" @click.self="attemptClose">
+      <div class="modal-panel" role="dialog" aria-modal="true">
+        <!-- Header: trash + close (or inline delete-confirm) -->
+        <div class="modal-header">
+          <template v-if="!deleteConfirm">
+            <h2 class="modal-title">{{ isEditMode ? "Edit Event" : "New Event" }}</h2>
+            <div class="header-actions">
+              <button
+                v-if="isEditMode"
+                class="header-btn header-btn-danger"
+                @click="deleteConfirm = true"
+                title="Delete event"
+                aria-label="Delete event"
+              ><Trash2 :size="16" /></button>
+              <button
+                class="header-btn"
+                @click="attemptClose"
+                title="Close"
+                aria-label="Close"
+              ><X :size="16" /></button>
+            </div>
+          </template>
+          <template v-else>
+            <span class="delete-confirm-prompt">Delete this event?</span>
+            <div class="header-actions">
+              <button
+                type="button"
+                class="btn-danger"
+                :disabled="deleting"
+                @click="doDelete"
+              >{{ deleting ? "Deleting…" : "Yes, delete" }}</button>
+              <button
+                type="button"
+                class="btn-confirm-cancel"
+                @click="deleteConfirm = false"
+              >No</button>
+            </div>
+          </template>
         </div>
 
-        <form class="so-form" @submit.prevent="save">
+        <!-- Body: form (scrolls if it gets long) -->
+        <form class="modal-form" @submit.prevent="attemptClose">
           <!-- Title -->
-          <div class="so-field">
-            <label class="so-label">Title <span class="required">*</span></label>
-            <input v-model="title" class="so-input" placeholder="Event title" autofocus />
+          <div class="form-field">
+            <label class="form-label">Title <span class="required">*</span></label>
+            <input v-model="title" class="form-input" placeholder="Event title" autofocus />
           </div>
 
           <!-- All-day toggle -->
-          <div class="so-field so-field-row">
-            <label class="so-label so-label-inline">All day</label>
+          <div class="form-field form-field-row">
+            <label class="form-label form-label-inline">All day</label>
             <button
               type="button"
               :class="['toggle-btn', { active: allDay }]"
@@ -281,74 +390,73 @@ async function doDelete() {
           </div>
 
           <!-- Start -->
-          <div class="so-field">
-            <label class="so-label">Start <span class="required">*</span></label>
+          <div class="form-field">
+            <label class="form-label">Start <span class="required">*</span></label>
             <div class="dt-row">
-              <input v-model="startDate" type="date" class="so-input dt-date" required />
-              <input v-if="!allDay" v-model="startTime" type="time" class="so-input dt-time" required />
+              <input v-model="startDate" type="date" class="form-input dt-date" required />
+              <input v-if="!allDay" v-model="startTime" type="time" class="form-input dt-time" required />
             </div>
-            <p v-if="isPastEvent" class="so-past-hint">This event is in the past</p>
+            <p v-if="isPastEvent" class="form-past-hint">This event is in the past</p>
           </div>
 
           <!-- End -->
-          <div class="so-field">
-            <label class="so-label">End</label>
+          <div class="form-field">
+            <label class="form-label">End</label>
             <div class="dt-row">
-              <input v-model="endDate" type="date" class="so-input dt-date" :min="startDate" />
-              <input v-if="!allDay" v-model="endTime" type="time" class="so-input dt-time" />
+              <input v-model="endDate" type="date" class="form-input dt-date" :min="startDate" />
+              <input v-if="!allDay" v-model="endTime" type="time" class="form-input dt-time" />
             </div>
           </div>
 
+          <!-- Recurrence -->
+          <div class="form-field">
+            <label class="form-label">Repeat</label>
+            <select v-model="recurrencePreset" class="form-input">
+              <option value="none">Does not repeat</option>
+              <option value="daily">Daily</option>
+              <option value="weekly">Weekly</option>
+              <option value="monthly">Monthly</option>
+              <option value="yearly">Yearly</option>
+              <option v-if="isCustomRecurrence" value="custom" disabled>Custom</option>
+            </select>
+            <p v-if="isCustomRecurrence" class="recurrence-custom-hint">
+              Custom rule: <code>{{ recurrence }}</code>
+              <br />
+              <span class="form-hint">Picking a preset will replace this rule.</span>
+            </p>
+          </div>
+
           <!-- Location -->
-          <div class="so-field">
-            <label class="so-label">Location <span class="so-hint">(optional)</span></label>
-            <input v-model="location" class="so-input" placeholder="Location" />
+          <div class="form-field">
+            <label class="form-label">Location <span class="form-hint">(optional)</span></label>
+            <input v-model="location" class="form-input" placeholder="Location" />
           </div>
 
           <!-- Description -->
-          <div class="so-field">
-            <label class="so-label">Description <span class="so-hint">(optional)</span></label>
-            <textarea v-model="description" class="so-input so-textarea" placeholder="Description" rows="3" />
+          <div class="form-field">
+            <label class="form-label">Description <span class="form-hint">(optional)</span></label>
+            <textarea v-model="description" class="form-input form-textarea" placeholder="Description" rows="3" />
           </div>
 
           <!-- Color -->
-          <div class="so-field so-field-row">
-            <label class="so-label so-label-inline">Color</label>
+          <div class="form-field form-field-row">
+            <label class="form-label form-label-inline">Color</label>
             <div class="color-row">
               <input v-model="color" type="color" class="color-picker" title="Pick event color" />
-              <input v-model="color" class="so-input color-hex" placeholder="#5B4A8A" />
+              <input v-model="color" class="form-input color-hex" placeholder="#5B4A8A" />
               <button v-if="color" type="button" class="btn-clear-color" @click="color = ''"><X :size="16" /></button>
             </div>
           </div>
 
           <!-- Project -->
-          <div class="so-field">
-            <label class="so-label">Project <span class="so-hint">(optional)</span></label>
+          <div class="form-field">
+            <label class="form-label">Project <span class="form-hint">(optional)</span></label>
             <ProjectSelector v-model="projectId" />
           </div>
 
-          <!-- Actions -->
-          <div class="so-actions">
-            <button type="submit" class="btn-primary" :disabled="saving">
-              {{ saving ? "Saving…" : (isEditMode ? "Save" : "Create") }}
-            </button>
-            <button type="button" class="btn-secondary" @click="emit('close')">Cancel</button>
-            <template v-if="isEditMode">
-              <button
-                v-if="!deleteConfirm"
-                type="button"
-                class="btn-danger-ghost"
-                @click="deleteConfirm = true"
-              >Delete</button>
-              <template v-else>
-                <span class="delete-confirm-label">Delete this event?</span>
-                <button type="button" class="btn-danger" :disabled="deleting" @click="doDelete">
-                  {{ deleting ? "Deleting…" : "Yes, delete" }}
-                </button>
-                <button type="button" class="btn-secondary" @click="deleteConfirm = false">No</button>
-              </template>
-            </template>
-          </div>
+          <!-- A hidden submit so Enter inside text inputs triggers attemptClose,
+               matching the no-explicit-Save-button intent: Enter commits. -->
+          <button type="submit" class="hidden-submit" :disabled="saving" tabindex="-1" aria-hidden="true" />
         </form>
       </div>
     </div>
@@ -356,81 +464,110 @@ async function doDelete() {
 </template>
 
 <style scoped>
-.slide-over-backdrop {
+.modal-backdrop {
   position: fixed;
   inset: 0;
-  background: rgba(0, 0, 0, 0.45);
+  background: rgba(0, 0, 0, 0.55);
   z-index: 200;
   display: flex;
-  justify-content: flex-end;
+  align-items: center;
+  justify-content: center;
+  padding: 1.25rem;
 }
 
-.slide-over-panel {
+.modal-panel {
   background: var(--color-surface, #1a1b1e);
-  border-left: 1px solid var(--color-border, #2a2b30);
-  width: min(440px, 100vw);
-  height: 100%;
-  overflow-y: auto;
+  border: 1px solid var(--color-border, #2a2b30);
+  border-radius: 12px;
+  width: min(480px, 100%);
+  max-height: calc(100vh - 2.5rem);
   display: flex;
   flex-direction: column;
-  box-shadow: -4px 0 24px rgba(0, 0, 0, 0.4);
+  box-shadow: 0 16px 40px rgba(0, 0, 0, 0.5);
+  overflow: hidden;
 }
 
-.so-header {
+.modal-header {
   display: flex;
   align-items: center;
   justify-content: space-between;
-  padding: 1.25rem 1.5rem;
+  gap: 0.75rem;
+  padding: 0.85rem 1rem 0.85rem 1.5rem;
   border-bottom: 1px solid var(--color-border, #2a2b30);
-  position: sticky;
-  top: 0;
   background: var(--color-surface, #1a1b1e);
-  z-index: 1;
+  min-height: 3rem;
 }
 
-.so-title {
+.modal-title {
   font-size: 1.05rem;
   font-weight: 500;
   margin: 0;
   color: var(--color-text, #e8e9f0);
 }
 
-.so-close {
+.header-actions {
+  display: flex;
+  align-items: center;
+  gap: 0.25rem;
+}
+
+.header-btn {
   background: none;
   border: none;
   color: var(--color-text-muted, #888);
   cursor: pointer;
-  font-size: 1.1rem;
-  padding: 0.25rem 0.4rem;
-  border-radius: 4px;
+  padding: 0.4rem;
+  border-radius: 6px;
   line-height: 1;
+  display: inline-flex;
+  align-items: center;
+  justify-content: center;
+  transition: background 0.15s, color 0.15s;
+}
+.header-btn:hover {
+  background: var(--color-hover, rgba(255,255,255,0.06));
+  color: var(--color-text, #e8e9f0);
 }
-.so-close:hover { background: var(--color-hover, rgba(255,255,255,0.06)); }
 
-.so-form {
-  padding: 1.25rem 1.5rem;
+/* Trash in header: subtle until hover, then Oxblood. Lower visual weight
+   than Save would have been — destructive actions shouldn't loom. */
+.header-btn-danger:hover {
+  background: var(--color-action-destructive);
+  color: #fff;
+}
+
+/* Inline delete-confirm prompt replaces the title row */
+.delete-confirm-prompt {
+  font-size: 0.95rem;
+  color: var(--color-text, #e8e9f0);
+  font-weight: 500;
+}
+
+/* Form scrolls inside the panel when content overflows */
+.modal-form {
+  padding: 1.25rem 1.5rem 1.5rem;
   display: flex;
   flex-direction: column;
   gap: 1.1rem;
-  flex: 1;
+  overflow-y: auto;
 }
 
-.so-field { display: flex; flex-direction: column; gap: 0.35rem; }
-.so-field-row { flex-direction: row; align-items: center; gap: 0.75rem; }
+.form-field { display: flex; flex-direction: column; gap: 0.35rem; }
+.form-field-row { flex-direction: row; align-items: center; gap: 0.75rem; }
 
-.so-label {
+.form-label {
   font-size: 0.78rem;
   font-weight: 500;
   color: var(--color-text-muted, #888);
   text-transform: uppercase;
   letter-spacing: 0.04em;
 }
-.so-label-inline { flex-shrink: 0; margin: 0; }
-.so-hint { font-weight: 400; text-transform: none; letter-spacing: 0; opacity: 0.7; }
+.form-label-inline { flex-shrink: 0; margin: 0; }
+.form-hint { font-weight: 400; text-transform: none; letter-spacing: 0; opacity: 0.7; }
 
 .required { color: #f87171; }
 
-.so-input {
+.form-input {
   background: var(--color-input-bg, #111113);
   border: 1px solid var(--color-border, #2a2b30);
   color: var(--color-text, #e8e9f0);
@@ -441,19 +578,35 @@ async function doDelete() {
   box-sizing: border-box;
   transition: border-color 0.15s;
 }
-.so-input:focus { outline: none; border-color: var(--color-primary); }
+.form-input:focus { outline: none; border-color: var(--color-primary); }
 
-.so-textarea { resize: vertical; min-height: 5rem; font-family: inherit; }
+.form-textarea { resize: vertical; min-height: 5rem; font-family: inherit; }
 
 .dt-row { display: flex; gap: 0.5rem; }
 .dt-date { flex: 1; }
 .dt-time { width: 7.5rem; flex-shrink: 0; }
-.so-past-hint {
+.form-past-hint {
   margin: 4px 0 0;
   font-size: 0.75rem;
   color: var(--color-text-secondary);
 }
 
+.recurrence-custom-hint {
+  margin: 4px 0 0;
+  font-size: 0.75rem;
+  color: var(--color-text-secondary);
+  line-height: 1.4;
+}
+.recurrence-custom-hint code {
+  background: var(--color-input-bg, #111113);
+  border: 1px solid var(--color-border, #2a2b30);
+  border-radius: 4px;
+  padding: 1px 5px;
+  font-family: var(--font-mono, ui-monospace, monospace);
+  font-size: 0.72rem;
+  color: var(--color-text, #e8e9f0);
+}
+
 .toggle-btn {
   background: var(--color-input-bg, #111113);
   border: 1px solid var(--color-border, #2a2b30);
@@ -482,65 +635,14 @@ async function doDelete() {
   font-size: 0.85rem;
 }
 
-.so-actions {
-  display: flex;
-  flex-wrap: wrap;
-  gap: 0.5rem;
-  padding-top: 0.5rem;
-  border-top: 1px solid var(--color-border, #2a2b30);
-  margin-top: auto;
-}
-
-/* Save (in slide-over): Moss action-primary */
-.btn-primary {
-  background: var(--color-action-primary);
-  color: #fff;
-  border: none;
-  border-radius: 8px;
-  padding: 0.55rem 1.2rem;
-  font-size: 0.9rem;
-  font-weight: 500;
-  cursor: pointer;
-  transition: background 0.15s;
-}
-.btn-primary:disabled { opacity: 0.5; cursor: not-allowed; }
-.btn-primary:hover:not(:disabled) { background: var(--color-action-primary-hover); }
-
-/* Cancel: Bronze action-secondary */
-.btn-secondary {
-  background: var(--color-action-secondary);
-  border: none;
-  color: #fff;
-  border-radius: 8px;
-  padding: 0.55rem 1rem;
-  font-size: 0.9rem;
-  cursor: pointer;
-  transition: background 0.15s;
-}
-.btn-secondary:hover { background: var(--color-action-secondary-hover); }
-
-/* Delete (entry-point): Oxblood action-destructive ghost */
-.btn-danger-ghost {
-  margin-left: auto;
-  background: none;
-  border: 1px solid var(--color-action-destructive);
-  color: var(--color-action-destructive);
-  border-radius: 8px;
-  padding: 0.55rem 1rem;
-  font-size: 0.9rem;
-  cursor: pointer;
-  transition: background 0.15s, color 0.15s;
-}
-.btn-danger-ghost:hover { background: var(--color-action-destructive); color: #fff; }
-
-/* Confirm-delete: Oxblood filled */
+/* Confirm-delete buttons (only shown during the inline confirm flow) */
 .btn-danger {
   background: var(--color-action-destructive);
   color: #fff;
   border: none;
-  border-radius: 8px;
-  padding: 0.55rem 1rem;
-  font-size: 0.9rem;
+  border-radius: 6px;
+  padding: 0.4rem 0.85rem;
+  font-size: 0.85rem;
   font-weight: 500;
   cursor: pointer;
   transition: background 0.15s;
@@ -548,9 +650,28 @@ async function doDelete() {
 .btn-danger:hover:not(:disabled) { background: var(--color-action-destructive-hover); }
 .btn-danger:disabled { opacity: 0.5; cursor: not-allowed; }
 
-.delete-confirm-label {
+.btn-confirm-cancel {
+  background: var(--color-action-secondary);
+  border: none;
+  color: #fff;
+  border-radius: 6px;
+  padding: 0.4rem 0.85rem;
   font-size: 0.85rem;
-  color: var(--color-text-muted, #888);
-  align-self: center;
+  cursor: pointer;
+  transition: background 0.15s;
+}
+.btn-confirm-cancel:hover { background: var(--color-action-secondary-hover); }
+
+/* Hidden submit lets Enter-in-text-input trigger the same close-with-save
+   path as X / Esc / backdrop. No visible Save button needed. */
+.hidden-submit {
+  position: absolute;
+  width: 1px;
+  height: 1px;
+  padding: 0;
+  margin: -1px;
+  overflow: hidden;
+  clip: rect(0,0,0,0);
+  border: 0;
 }
 </style>

frontend/src/views/SettingsView.vue

@@ -4,7 +4,7 @@ import { ref, computed, watch, onMounted } from "vue";
 import { useSettingsStore } from "@/stores/settings";
 import { useAuthStore } from "@/stores/auth";
 import { useToastStore } from "@/stores/toast";
-import { apiGet, apiPost, apiPut, apiDelete, listGroups, createGroup, deleteGroup, listGroupMembers, addGroupMember, removeGroupMember, searchUsers, getFableMcpInfo, listApiKeys, createApiKey as apiCreateApiKey, revokeApiKey as apiRevokeApiKey, getVoiceStatus, getVoiceList, synthesiseSpeech, getProfile, updateProfile, consolidateProfile, clearProfileObservations, getJournalConfig, saveJournalConfig, geocodeAddress, type ApiKeyEntry, type GroupEntry, type GroupMember, type UserSearchResult, type VoiceStatusResult, type VoiceEntry, type VoiceBlendEntry, type UserProfile, type JournalConfig } from "@/api/client";
+import { apiGet, apiPost, apiPut, apiDelete, listGroups, createGroup, deleteGroup, listGroupMembers, addGroupMember, removeGroupMember, searchUsers, getFableMcpInfo, listApiKeys, createApiKey as apiCreateApiKey, revokeApiKey as apiRevokeApiKey, getVoiceStatus, getVoiceList, synthesiseSpeech, getProfile, updateProfile, consolidateProfile, clearProfileObservations, listProfileObservations, getJournalConfig, saveJournalConfig, geocodeAddress, type ApiKeyEntry, type GroupEntry, type GroupMember, type UserSearchResult, type VoiceStatusResult, type VoiceEntry, type VoiceBlendEntry, type UserProfile, type JournalConfig, type ProfileObservationEntry } from "@/api/client";
 import { usePushStore } from "@/stores/push";
 import type { User } from "@/types/auth";
 import PaginationBar from "@/components/PaginationBar.vue";
@@ -549,6 +549,26 @@ const profileSaving = ref(false)
 const profileSaved = ref(false)
 const consolidating = ref(false)
 const clearingObs = ref(false)
+const observations = ref<ProfileObservationEntry[]>([])
+const observationsExpanded = ref(false)
+const observationsLoading = ref(false)
+const observationsLoaded = ref(false)
+
+async function toggleObservations() {
+  observationsExpanded.value = !observationsExpanded.value
+  if (observationsExpanded.value && !observationsLoaded.value) {
+    observationsLoading.value = true
+    try {
+      const res = await listProfileObservations()
+      observations.value = res.observations
+      observationsLoaded.value = true
+    } catch {
+      toastStore.show('Failed to load observations', 'error')
+    } finally {
+      observationsLoading.value = false
+    }
+  }
+}
 
 async function loadProfile() {
   try { profile.value = await getProfile() } catch { /* non-critical */ }
@@ -582,6 +602,17 @@ function toggleProfileWorkDay(day: string) {
   profile.value.work_schedule = { ...profile.value.work_schedule, days }
 }
 
+async function onToggleCloseout(enabled: boolean) {
+  journalConfig.value.closeout_enabled = enabled
+  try {
+    await saveJournalConfig(journalConfig.value)
+    toastStore.show(enabled ? 'Nightly closeout enabled' : 'Nightly closeout disabled')
+  } catch {
+    journalConfig.value.closeout_enabled = !enabled  // revert UI on failure
+    toastStore.show('Failed to update closeout setting', 'error')
+  }
+}
+
 async function runConsolidate() {
   consolidating.value = true
   try {
@@ -600,6 +631,7 @@ const journalConfig = ref<JournalConfig>({
   prep_hour: 5,
   prep_minute: 0,
   day_rollover_hour: 4,
+  closeout_enabled: true,
   locations: { home: { label: 'Home', address: '' }, work: { label: 'Work', address: '' } },
   temp_unit: 'C',
 })
@@ -620,6 +652,7 @@ async function loadJournalConfig() {
       prep_hour: cfg.prep_hour ?? 5,
       prep_minute: cfg.prep_minute ?? 0,
       day_rollover_hour: cfg.day_rollover_hour ?? 4,
+      closeout_enabled: cfg.closeout_enabled ?? true,
       morning_end_hour: cfg.morning_end_hour,
       midday_end_hour: cfg.midday_end_hour,
       locations: {
@@ -689,6 +722,8 @@ async function clearObservations() {
     profile.value.learned_summary = ''
     profile.value.observations_count = 0
     profile.value.observations_updated_at = null
+    observations.value = []
+    observationsLoaded.value = false
     toastStore.show('Learned data cleared')
   } catch { toastStore.show('Failed to clear observations', 'error') }
   finally { clearingObs.value = false }
@@ -1901,8 +1936,38 @@ function formatUserDate(iso: string): string {
           The assistant observes patterns from your journal and chat conversations and builds a summary over time. The summary is included in the journal's system prompt so the daily prep can reference what it knows about you.
           <span v-if="profile.observations_count > 0"> {{ profile.observations_count }} raw observation{{ profile.observations_count !== 1 ? 's' : '' }} stored.</span>
         </p>
+
+        <label class="toggle-row" style="display:flex;align-items:center;gap:0.6rem;margin:0.5rem 0 0.75rem">
+          <input
+            type="checkbox"
+            :checked="journalConfig.closeout_enabled !== false"
+            @change="onToggleCloseout(($event.target as HTMLInputElement).checked)"
+          />
+          <span>
+            <strong>Nightly closeout</strong>
+            <small style="display:block;color:var(--color-text-muted)">Extracts patterns from yesterday's journal at your day-rollover hour.</small>
+          </span>
+        </label>
+
         <div v-if="profile.learned_summary" class="learned-summary">{{ profile.learned_summary }}</div>
         <div v-else class="learned-empty">No learned summary yet. Observations accumulate from journal and chat conversations.</div>
+
+        <div class="observations-panel" style="margin-top:0.75rem">
+          <button class="btn-secondary" @click="toggleObservations" :disabled="profile.observations_count === 0">
+            {{ observationsExpanded ? '▾' : '▸' }} Recent observations ({{ profile.observations_count }})
+          </button>
+          <div v-if="observationsExpanded" class="observations-list" style="margin-top:0.5rem;padding:0.5rem 0.75rem;border:1px solid var(--color-border);border-radius:var(--radius-md);background:var(--color-bg-elev-1)">
+            <div v-if="observationsLoading">Loading…</div>
+            <div v-else-if="observations.length === 0">No observations yet.</div>
+            <div v-else>
+              <div v-for="entry in observations" :key="entry.date" style="margin-bottom:0.75rem">
+                <div style="font-weight:600;font-size:0.875rem;color:var(--color-text-muted)">{{ entry.date }}</div>
+                <div style="white-space:pre-wrap;font-size:0.9rem">{{ entry.bullets }}</div>
+              </div>
+            </div>
+          </div>
+        </div>
+
         <div class="actions" style="gap:0.5rem;flex-wrap:wrap">
           <button class="btn-secondary" @click="runConsolidate" :disabled="consolidating || profile.observations_count === 0">
             {{ consolidating ? 'Consolidating…' : 'Consolidate Now' }}

src/fabledassistant/models/event.py

@@ -1,4 +1,4 @@
-from datetime import datetime, timezone
+from datetime import datetime, timedelta, timezone
 
 from sqlalchemy import Boolean, DateTime, ForeignKey, Integer, Text
 from sqlalchemy.orm import Mapped, mapped_column
@@ -20,7 +20,11 @@ class Event(Base):
     uid: Mapped[str] = mapped_column(Text)
     title: Mapped[str] = mapped_column(Text, default="")
     start_dt: Mapped[datetime] = mapped_column(DateTime(timezone=True))
-    end_dt: Mapped[datetime | None] = mapped_column(DateTime(timezone=True), nullable=True)
+    # Duration in minutes; NULL = point event with no end specified.
+    # Replaces the prior `end_dt` column (Fable #160 / migration 0043).
+    # The DB has a CHECK constraint that this is NULL or >= 0, so an
+    # event whose end is before its start is structurally inexpressible.
+    duration_minutes: Mapped[int | None] = mapped_column(Integer, nullable=True)
     all_day: Mapped[bool] = mapped_column(Boolean, default=False)
     description: Mapped[str] = mapped_column(Text, default="")
     location: Mapped[str] = mapped_column(Text, default="")
@@ -38,7 +42,21 @@ class Event(Base):
         onupdate=lambda: datetime.now(timezone.utc),
     )
 
+    @property
+    def end_dt(self) -> datetime | None:
+        """Derived end datetime: ``start_dt + duration_minutes``.
+
+        Returns ``None`` for point events (``duration_minutes is None``).
+        Computed at access time rather than stored — a stored end was
+        the source of the "end before start" corruption that motivated
+        this redesign.
+        """
+        if self.duration_minutes is None:
+            return None
+        return self.start_dt + timedelta(minutes=self.duration_minutes)
+
     def to_dict(self) -> dict:
+        end_dt = self.end_dt
         return {
             "id": self.id,
             "user_id": self.user_id,
@@ -47,7 +65,8 @@ class Event(Base):
             "project_id": self.project_id,
             "title": self.title,
             "start_dt": self.start_dt.isoformat() if self.start_dt else None,
-            "end_dt": self.end_dt.isoformat() if self.end_dt else None,
+            "end_dt": end_dt.isoformat() if end_dt else None,
+            "duration_minutes": self.duration_minutes,
             "all_day": self.all_day,
             "description": self.description,
             "location": self.location,

src/fabledassistant/routes/events.py

@@ -54,19 +54,23 @@ async def create_event():
         end_dt = _parse_dt(data["end_dt"]) if data.get("end_dt") else None
     except ValueError:
         return jsonify({"error": "Invalid datetime format"}), 400
-    event = await events_svc.create_event(
-        user_id=_get_current_user_id(),
-        title=data["title"],
-        start_dt=start_dt,
-        end_dt=end_dt,
-        all_day=data.get("all_day", False),
-        description=data.get("description", ""),
-        location=data.get("location", ""),
-        color=data.get("color", ""),
-        recurrence=data.get("recurrence"),
-        project_id=data.get("project_id"),
-        reminder_minutes=data.get("reminder_minutes"),
-    )
+    try:
+        event = await events_svc.create_event(
+            user_id=_get_current_user_id(),
+            title=data["title"],
+            start_dt=start_dt,
+            end_dt=end_dt,
+            duration_minutes=data.get("duration_minutes"),
+            all_day=data.get("all_day", False),
+            description=data.get("description", ""),
+            location=data.get("location", ""),
+            color=data.get("color", ""),
+            recurrence=data.get("recurrence"),
+            project_id=data.get("project_id"),
+            reminder_minutes=data.get("reminder_minutes"),
+        )
+    except ValueError as exc:
+        return jsonify({"error": str(exc)}), 400
     return jsonify(event.to_dict()), 201
 
 
@@ -93,7 +97,7 @@ async def update_event(event_id: int):
     for bool_field in ("all_day",):
         if bool_field in data:
             fields[bool_field] = data[bool_field]
-    for int_field in ("project_id", "reminder_minutes"):
+    for int_field in ("project_id", "reminder_minutes", "duration_minutes"):
         if int_field in data:
             fields[int_field] = data[int_field]
     for dt_field in ("start_dt", "end_dt"):
@@ -106,11 +110,14 @@ async def update_event(event_id: int):
                     fields[dt_field] = _parse_dt(data[dt_field])
                 except ValueError:
                     return jsonify({"error": f"Invalid datetime for {dt_field}"}), 400
-    event = await events_svc.update_event(
-        user_id=_get_current_user_id(),
-        event_id=event_id,
-        **fields,
-    )
+    try:
+        event = await events_svc.update_event(
+            user_id=_get_current_user_id(),
+            event_id=event_id,
+            **fields,
+        )
+    except ValueError as exc:
+        return jsonify({"error": str(exc)}), 400
     if event is None:
         return jsonify({"error": "Event not found"}), 404
     return jsonify(event.to_dict())

src/fabledassistant/routes/journal.py

@@ -66,6 +66,17 @@ async def _resolve_config(user_id: int) -> dict:
     return {**DEFAULT_JOURNAL_CONFIG, **config}
 
 
+def _valid_location_keys(cfg: dict) -> set[str]:
+    """Keys in ``cfg.locations`` that have a usable lat/lon. Anything else
+    (orphaned cache rows, locations the user typed but didn't geocode) is
+    excluded so it can't render as a fake site in the UI."""
+    locations = cfg.get("locations") or {}
+    return {
+        key for key, loc in locations.items()
+        if isinstance(loc, dict) and loc.get("lat") is not None and loc.get("lon") is not None
+    }
+
+
 @journal_bp.get("/config")
 @login_required
 async def get_config():
@@ -82,9 +93,41 @@ async def put_config():
         return jsonify({"error": "config must be an object"}), 400
     await set_setting(user_id, "journal_config", json.dumps(body))
     await update_user_schedule(user_id)
+
+    # Trigger a background weather refresh for any newly-saved location with
+    # valid lat/lon. Without this, the cache row for the location doesn't
+    # exist (or stays stale) until the user clicks the manual refresh button,
+    # so the journal weather panel renders empty for newly-entered sites.
+    valid_locs = [
+        (key, loc)
+        for key, loc in (body.get("locations") or {}).items()
+        if isinstance(loc, dict) and loc.get("lat") is not None and loc.get("lon") is not None
+    ]
+    if valid_locs:
+        asyncio.create_task(_refresh_locations_in_background(user_id, valid_locs))
+
     return jsonify({"ok": True})
 
 
+async def _refresh_locations_in_background(
+    user_id: int, locations: list[tuple[str, dict]]
+) -> None:
+    for key, loc in locations:
+        try:
+            await weather_svc.refresh_location_cache(
+                user_id=user_id,
+                location_key=key,
+                location_label=loc.get("label", key),
+                lat=loc["lat"],
+                lon=loc["lon"],
+            )
+        except Exception:
+            logger.warning(
+                "Post-save weather refresh failed for user %d / %s",
+                user_id, key, exc_info=True,
+            )
+
+
 @journal_bp.get("/today")
 @login_required
 async def get_today():
@@ -258,7 +301,9 @@ async def _refresh_stale_in_background(user_id: int, stale_keys: set[str]) -> No
 @login_required
 async def get_weather():
     user_id = get_current_user_id()
-    rows = await weather_svc.get_cached_weather_rows(user_id)
+    cfg = await _resolve_config(user_id)
+    valid_keys = _valid_location_keys(cfg)
+    rows = await weather_svc.get_cached_weather_rows(user_id, valid_keys)
     temp_unit = await _journal_temp_unit(user_id)
 
     # Kick off a best-effort background refresh for stale rows so the next page
@@ -318,7 +363,8 @@ async def refresh_weather():
             )
         except Exception:
             logger.warning("Failed to refresh weather for %s", key, exc_info=True)
-    rows = await weather_svc.get_cached_weather_rows(user_id)
+    valid_keys = _valid_location_keys(cfg)
+    rows = await weather_svc.get_cached_weather_rows(user_id, valid_keys)
     cards = [
         card for row in rows
         if (card := weather_svc.parse_weather_card_data(row, temp_unit)) is not None

src/fabledassistant/routes/profile.py

@@ -59,3 +59,13 @@ async def clear_observations():
     uid = get_current_user_id()
     await clear_learned_data(uid)
     return jsonify({"status": "ok"})
+
+
+@profile_bp.route("/observations", methods=["GET"])
+@login_required
+async def list_observations():
+    uid = get_current_user_id()
+    profile = await get_profile(uid)
+    raw = list(profile.observations_raw or [])
+    # Newest first, last 14 entries
+    return jsonify({"observations": list(reversed(raw[-14:]))})

src/fabledassistant/services/caldav_sync.py

@@ -130,6 +130,17 @@ async def sync_user_events(user_id: int) -> dict:
     async with async_session() as session:
         for ev in remote_events:
             caldav_uid = ev["caldav_uid"]
+            # Storage uses duration, not end_dt. Convert here so the
+            # rest of this function can compare/upsert in one shape.
+            ev_start = ev["start_dt"]
+            ev_end = ev["end_dt"]
+            ev_duration = (
+                int((ev_end - ev_start).total_seconds() // 60)
+                if ev_end is not None and ev_start is not None and ev_end > ev_start
+                else None
+            )
+            ev["duration_minutes"] = ev_duration
+
             result = await session.execute(
                 select(Event).where(
                     Event.user_id == user_id,
@@ -145,8 +156,8 @@ async def sync_user_events(user_id: int) -> dict:
                     uid=str(uuid.uuid4()),
                     caldav_uid=caldav_uid,
                     title=ev["title"],
-                    start_dt=ev["start_dt"],
-                    end_dt=ev["end_dt"],
+                    start_dt=ev_start,
+                    duration_minutes=ev_duration,
                     all_day=ev["all_day"],
                     description=ev["description"],
                     location=ev["location"],
@@ -157,7 +168,7 @@ async def sync_user_events(user_id: int) -> dict:
             else:
                 # Update if anything changed
                 changed = False
-                for field in ("title", "start_dt", "end_dt", "all_day", "description", "location", "recurrence"):
+                for field in ("title", "start_dt", "duration_minutes", "all_day", "description", "location", "recurrence"):
                     if getattr(existing, field) != ev[field]:
                         setattr(existing, field, ev[field])
                         changed = True

src/fabledassistant/services/calendar_sync.py

@@ -207,6 +207,14 @@ async def sync_event_to_db(user_id: int, ical_uid: str) -> Event | None:
                 d = dtend.dt
                 end_dt = datetime(d.year, d.month, d.day, tzinfo=timezone.utc)
 
+            # Storage uses duration, not end_dt. Convert iCal DTEND to a
+            # minute count anchored on DTSTART. Treat invalid (end <= start)
+            # incoming data as a point event rather than rejecting; we
+            # don't control external CalDAV writers.
+            duration_minutes = None
+            if end_dt is not None and end_dt > start_dt:
+                duration_minutes = int((end_dt - start_dt).total_seconds() // 60)
+
             async with async_session() as session:
                 result = await session.execute(
                     select(Event).where(Event.user_id == user_id, Event.uid == ical_uid)
@@ -215,7 +223,7 @@ async def sync_event_to_db(user_id: int, ical_uid: str) -> Event | None:
                 if existing:
                     existing.title = title
                     existing.start_dt = start_dt
-                    existing.end_dt = end_dt
+                    existing.duration_minutes = duration_minutes
                     existing.all_day = all_day
                     existing.description = description
                     existing.location = location
@@ -230,7 +238,7 @@ async def sync_event_to_db(user_id: int, ical_uid: str) -> Event | None:
                         uid=ical_uid,
                         title=title,
                         start_dt=start_dt,
-                        end_dt=end_dt,
+                        duration_minutes=duration_minutes,
                         all_day=all_day,
                         description=description,
                         location=location,

src/fabledassistant/services/events.py

@@ -1,4 +1,13 @@
-"""Internal event store service with CalDAV push sync."""
+"""Internal event store service with CalDAV push sync.
+
+Storage model: an event is anchored at ``start_dt`` and has an optional
+``duration_minutes``. The end of the event is *derived* via
+``Event.end_dt`` (a Python property), never stored. Callers may still
+pass ``end_dt`` on writes for ergonomic compatibility — the service
+converts to ``duration_minutes`` internally. This rules out the entire
+"end before start" bug class structurally (Fable #160 / migration
+0043). Open-ended events use ``duration_minutes = None``.
+"""
 from __future__ import annotations
 
 import asyncio
@@ -7,7 +16,7 @@ import uuid
 from datetime import datetime, timedelta, timezone
 
 from dateutil.rrule import rrulestr
-from sqlalchemy import and_, or_, select
+from sqlalchemy import or_, select
 
 from fabledassistant.models import async_session
 from fabledassistant.models.event import Event
@@ -15,11 +24,56 @@ from fabledassistant.models.event import Event
 logger = logging.getLogger(__name__)
 
 
+def _normalize_duration(
+    *,
+    start_dt: datetime,
+    end_dt: datetime | None,
+    duration_minutes: int | None,
+) -> int | None:
+    """Reduce (end_dt, duration_minutes) inputs to a single canonical
+    ``duration_minutes`` value.
+
+    Resolution order:
+      1. If ``duration_minutes`` is explicit, use it (validate >= 0).
+         If ``end_dt`` is also given, validate the two agree.
+      2. Otherwise, derive from ``end_dt - start_dt``.
+      3. Otherwise None (point event with no end).
+
+    Raises ``ValueError`` for any invalid combination — duration < 0,
+    end_dt < start_dt, or end_dt and duration_minutes inconsistent.
+    """
+    if duration_minutes is not None:
+        if duration_minutes < 0:
+            raise ValueError(
+                f"duration_minutes must be >= 0, got {duration_minutes}"
+            )
+        if end_dt is not None:
+            expected = int((end_dt - start_dt).total_seconds() // 60)
+            if expected != duration_minutes:
+                raise ValueError(
+                    f"end_dt ({end_dt.isoformat()}) implies "
+                    f"{expected} minutes but duration_minutes={duration_minutes} "
+                    f"was passed; pass only one or make them agree."
+                )
+        return duration_minutes
+    if end_dt is not None:
+        delta_seconds = (end_dt - start_dt).total_seconds()
+        if delta_seconds < 0:
+            raise ValueError(
+                f"end_dt ({end_dt.isoformat()}) must be at or after "
+                f"start_dt ({start_dt.isoformat()}); pass end_dt=None "
+                f"or omit it for point events."
+            )
+        return int(delta_seconds // 60)
+    return None
+
+
 async def create_event(
     user_id: int,
     title: str,
     start_dt: datetime,
     end_dt: datetime | None = None,
+    duration_minutes: int | None = None,
     all_day: bool = False,
     description: str = "",
     location: str = "",
@@ -27,12 +81,25 @@ async def create_event(
     recurrence: str | None = None,
     project_id: int | None = None,
     reminder_minutes: int | None = None,
-    # CalDAV-only fields (not stored in DB, forwarded to push)
+    # ``duration`` is a legacy alias kept for the calendar tool layer
+    # and CalDAV pass-through callers; promotes to duration_minutes
+    # when duration_minutes isn't otherwise specified.
     duration: int | None = None,
     attendees: list[str] | None = None,
     calendar_name: str | None = None,
 ) -> Event:
-    """Create an event in the DB, then fire a CalDAV push task."""
+    """Create an event in the DB, then fire a CalDAV push task.
+
+    Either ``end_dt`` or ``duration_minutes`` may be supplied; the
+    service converts to ``duration_minutes`` internally. Raises
+    ``ValueError`` on invalid combinations (negative duration, end
+    before start, end/duration disagreement).
+    """
+    if duration is not None and duration_minutes is None:
+        duration_minutes = duration
+    duration_minutes = _normalize_duration(
+        start_dt=start_dt, end_dt=end_dt, duration_minutes=duration_minutes,
+    )
     uid = str(uuid.uuid4())
     async with async_session() as session:
         event = Event(
@@ -40,7 +107,7 @@ async def create_event(
             uid=uid,
             title=title,
             start_dt=start_dt,
-            end_dt=end_dt,
+            duration_minutes=duration_minutes,
             all_day=all_day,
             description=description,
             location=location,
@@ -54,7 +121,7 @@ async def create_event(
         await session.refresh(event)
 
     extra_fields = {
-        "duration": duration,
+        "duration": duration_minutes,
         "reminder_minutes": reminder_minutes,
         "attendees": attendees,
         "calendar_name": calendar_name,
@@ -80,66 +147,74 @@ async def list_events(
     """List events for user_id that overlap [date_from, date_to].
 
     Recurring events (with an RRULE recurrence string) are expanded into
-    individual occurrences within the range.  Non-recurring events are
-    returned as-is.  All results are sorted by start time and returned as
-    dicts (same shape as Event.to_dict()).
+    individual occurrences within the range. Non-recurring events are
+    returned as-is. All results are sorted by start time and returned as
+    dicts (same shape as ``Event.to_dict()``).
+
+    Filtering strategy: a coarse SQL prefilter (events that start on or
+    before ``date_to``), then refine in Python using the event's derived
+    end (``start_dt + duration_minutes``). Doing the end-of-event math
+    in SQL would require Postgres-specific interval arithmetic; the
+    Python-side refinement is a few row-loops over a small per-user
+    result set, which is fine for personal-scale data and avoids
+    coupling the query to a specific dialect.
     """
     async with async_session() as session:
-        # Match strategy:
-        #   - Recurring events: fetch all, expand via rrule below.
-        #   - Non-recurring with an end_dt: standard overlap — starts before
-        #     date_to and ends after date_from.
-        #   - Non-recurring with no end_dt: treat as a point event at
-        #     start_dt, include only if start_dt falls within the window.
-        #     (Previously this branch matched any event with a null end_dt,
-        #     returning all past events as "happening today".)
         result = await session.execute(
-            select(Event).where(
+            select(Event)
+            .where(
                 Event.user_id == user_id,
                 or_(
                     Event.recurrence.isnot(None),
-                    and_(
-                        Event.recurrence.is_(None),
-                        Event.start_dt <= date_to,
-                        or_(
-                            Event.end_dt >= date_from,
-                            and_(
-                                Event.end_dt.is_(None),
-                                Event.start_dt >= date_from,
-                            ),
-                        ),
-                    ),
+                    Event.start_dt <= date_to,
                 ),
-            ).order_by(Event.start_dt)
+            )
+            .order_by(Event.start_dt)
         )
         events = list(result.scalars().all())
 
     items: list[dict] = []
     for event in events:
-        if not event.recurrence:
-            items.append(event.to_dict())
+        if event.recurrence:
+            duration = (
+                timedelta(minutes=event.duration_minutes)
+                if event.duration_minutes is not None
+                else None
+            )
+            try:
+                rule = rrulestr(event.recurrence, dtstart=event.start_dt, ignoretz=False)
+                occurrences = rule.between(date_from, date_to, inc=True)
+            except Exception:
+                logger.warning("Failed to expand RRULE for event %d: %r", event.id, event.recurrence)
+                # Fall back to canonical event row; still apply the
+                # window check so a far-future canonical row doesn't
+                # leak into today's list.
+                if date_from <= event.start_dt <= date_to:
+                    items.append(event.to_dict())
+                continue
+
+            base = event.to_dict()
+            for occ in occurrences:
+                if occ.tzinfo is None:
+                    occ = occ.replace(tzinfo=timezone.utc)
+                occurrence_dict = dict(base)
+                occurrence_dict["start_dt"] = occ.isoformat()
+                if duration is not None:
+                    occurrence_dict["end_dt"] = (occ + duration).isoformat()
+                items.append(occurrence_dict)
             continue
 
-        # Expand recurring event occurrences within [date_from, date_to]
-        duration = (event.end_dt - event.start_dt) if event.end_dt else None
-        try:
-            rule = rrulestr(event.recurrence, dtstart=event.start_dt, ignoretz=False)
-            occurrences = rule.between(date_from, date_to, inc=True)
-        except Exception:
-            logger.warning("Failed to expand RRULE for event %d: %r", event.id, event.recurrence)
-            items.append(event.to_dict())
-            continue
-
-        base = event.to_dict()
-        for occ in occurrences:
-            # Ensure occurrence is UTC-aware
-            if occ.tzinfo is None:
-                occ = occ.replace(tzinfo=timezone.utc)
-            occurrence_dict = dict(base)
-            occurrence_dict["start_dt"] = occ.isoformat()
-            if duration is not None:
-                occurrence_dict["end_dt"] = (occ + duration).isoformat()
-            items.append(occurrence_dict)
+        # Non-recurring: refine the coarse prefilter in Python using the
+        # derived end_dt. A point event (duration None) is included when
+        # its start is at or after date_from. A timed event is included
+        # when its end is at or after date_from.
+        derived_end = event.end_dt
+        if derived_end is None:
+            if event.start_dt >= date_from:
+                items.append(event.to_dict())
+        else:
+            if derived_end >= date_from:
+                items.append(event.to_dict())
 
     items.sort(key=lambda x: x["start_dt"])
     return items
@@ -173,7 +248,13 @@ async def search_events(
 
 
 async def update_event(user_id: int, event_id: int, **fields) -> Event | None:
-    """Partial update. Returns updated event or None if not found."""
+    """Partial update. Returns updated event or None if not found.
+
+    Accepts ``end_dt`` or ``duration_minutes`` (or both, validated for
+    agreement). The service converts to ``duration_minutes`` before
+    persisting; ``end_dt`` is never stored. Raises ``ValueError`` for
+    invalid combinations against the post-update state.
+    """
     async with async_session() as session:
         result = await session.execute(
             select(Event).where(Event.id == event_id, Event.user_id == user_id)
@@ -182,10 +263,39 @@ async def update_event(user_id: int, event_id: int, **fields) -> Event | None:
         if event is None:
             return None
         old_title = event.title  # capture before mutation for CalDAV lookup
-        allowed = {"title", "start_dt", "end_dt", "all_day", "description",
-                   "location", "color", "recurrence", "project_id", "reminder_minutes"}
-        # Nullable fields that callers can explicitly set to None to clear
-        nullable = {"end_dt", "recurrence", "project_id", "reminder_minutes"}
+
+        # Resolve any end_dt/duration_minutes inputs against the
+        # post-update start_dt. If neither is in the patch, leave the
+        # existing duration_minutes alone.
+        post_update_start = (
+            fields["start_dt"]
+            if fields.get("start_dt") is not None
+            else event.start_dt
+        )
+        if "end_dt" in fields or "duration_minutes" in fields:
+            new_end = fields.pop("end_dt", None)
+            new_duration = fields.pop("duration_minutes", None)
+            # If end_dt is in the patch but explicitly None, that's a
+            # clear → duration_minutes = None. Same shape duration_minutes=None.
+            if new_end is None and new_duration is None:
+                fields["duration_minutes"] = None
+            else:
+                fields["duration_minutes"] = _normalize_duration(
+                    start_dt=post_update_start,
+                    end_dt=new_end,
+                    duration_minutes=new_duration,
+                )
+
+        allowed = {
+            "title", "start_dt", "duration_minutes", "all_day",
+            "description", "location", "color", "recurrence",
+            "project_id", "reminder_minutes",
+        }
+        # Nullable fields callers can explicitly clear by passing None
+        nullable = {
+            "duration_minutes", "recurrence", "project_id",
+            "reminder_minutes",
+        }
         for key, value in fields.items():
             if key in allowed and (value is not None or key in nullable):
                 setattr(event, key, value)
@@ -255,11 +365,12 @@ async def _push_create(event: Event, user_id: int, extra: dict) -> None:
         )
         if not await is_caldav_configured(user_id):
             return
+        derived_end = event.end_dt  # property: start + duration_minutes
         await caldav_create(
             user_id=user_id,
             title=event.title,
             start=event.start_dt.isoformat(),
-            end=event.end_dt.isoformat() if event.end_dt else None,
+            end=derived_end.isoformat() if derived_end else None,
             description=event.description or None,
             location=event.location or None,
             all_day=event.all_day,
@@ -296,12 +407,13 @@ async def _push_update(event: Event, user_id: int, old_title: str = "") -> None:
             return
         # Use old_title so CalDAV can find the event even if the title was changed
         query_title = old_title or event.title
+        derived_end = event.end_dt
         await caldav_update(
             user_id=user_id,
             query=query_title,
             title=event.title,
             start=event.start_dt.isoformat(),
-            end=event.end_dt.isoformat() if event.end_dt else None,
+            end=derived_end.isoformat() if derived_end else None,
             description=event.description or None,
             location=event.location or None,
         )

src/fabledassistant/services/journal_closeout.py

@@ -0,0 +1,133 @@
+"""Journal closeout — nightly extraction of profile observations.
+
+Runs once per user per day at day_rollover_hour. Reads yesterday's /journal
+conversation, filters out assistant-authored auto-content (daily prep),
+asks the background LLM to extract user-side patterns/habits, and appends
+the bullets to user_profiles.observations_raw via append_observations.
+"""
+from __future__ import annotations
+
+import datetime
+import logging
+
+from sqlalchemy import or_, select
+
+from fabledassistant.config import Config
+from fabledassistant.models import async_session
+from fabledassistant.models.conversation import Conversation, Message
+from fabledassistant.services.llm import generate_completion
+from fabledassistant.services.settings import get_setting
+from fabledassistant.services.user_profile import append_observations
+
+logger = logging.getLogger(__name__)
+
+# Message kinds whose content must NEVER be sent to the closeout LLM.
+# These are assistant-authored auto-blocks that would otherwise dominate
+# attention and leak back into "what the assistant has learned."
+EXCLUDED_KINDS: set[str] = {"daily_prep"}
+
+
+def _filter_messages(messages):
+    """Drop messages whose msg_metadata.kind is in EXCLUDED_KINDS.
+
+    Accepts any iterable of message-like objects with `role`, `content`,
+    and `msg_metadata` attributes (real Message rows or SimpleNamespace).
+    """
+    kept = []
+    for m in messages:
+        meta = getattr(m, "msg_metadata", None) or {}
+        if meta.get("kind") in EXCLUDED_KINDS:
+            continue
+        kept.append(m)
+    return kept
+
+
+_TRANSCRIPT_WINDOW = 20
+_CONTENT_CAP = 500
+
+
+def _build_transcript(messages) -> str:
+    """Format the last 20 messages as `ROLE: content[:500]` lines."""
+    tail = list(messages)[-_TRANSCRIPT_WINDOW:]
+    return "\n".join(
+        f"{m.role.upper()}: {m.content[:_CONTENT_CAP]}" for m in tail
+    )
+
+
+SYSTEM_PROMPT = (
+    "You are reviewing a day's journal conversation to extract preference "
+    "observations the USER revealed about themselves.\n\n"
+    "Rules:\n"
+    "- Only extract patterns, habits, recurring frustrations, or contextual "
+    "facts the user said or demonstrated.\n"
+    "- DO NOT restate facts that belong in structured fields: name, job title, "
+    "industry, expertise level, response style, tone, interests. Those are "
+    "handled separately.\n"
+    "- DO NOT extract anything from the ASSISTANT turns about the user — only "
+    "what the user themselves stated or demonstrated by their choices.\n"
+    "- Write 2-5 short bullet points. Be specific and factual.\n"
+    "- If nothing notable, output only: (nothing to note)"
+)
+
+
+async def run_for_user(user_id: int, yesterday: datetime.date) -> None:
+    """Extract preference observations from yesterday's journal conversation.
+
+    Skips silently when there is nothing meaningful to extract.
+    """
+    async with async_session() as session:
+        conv_result = await session.execute(
+            select(Conversation).where(
+                Conversation.user_id == user_id,
+                Conversation.conversation_type == "journal",
+                Conversation.day_date == yesterday,
+            )
+        )
+        conv = conv_result.scalar_one_or_none()
+        if conv is None:
+            logger.debug("closeout: no journal conv for user %d on %s", user_id, yesterday)
+            return
+
+        msg_result = await session.execute(
+            select(Message)
+            .where(
+                Message.conversation_id == conv.id,
+                Message.role.in_(("user", "assistant")),
+                or_(
+                    Message.msg_metadata.is_(None),
+                    ~Message.msg_metadata["kind"].astext.in_(EXCLUDED_KINDS),
+                ),
+            )
+            .order_by(Message.created_at)
+        )
+        messages = list(msg_result.scalars().all())
+
+    # Defensive second-pass filter (covers any message with metadata the
+    # SQL JSON path can't reach, e.g. older rows where kind nesting differs).
+    messages = _filter_messages(messages)
+
+    if len(messages) < 2:
+        logger.debug("closeout: not enough messages for user %d (%d)", user_id, len(messages))
+        return
+
+    transcript = _build_transcript(messages)
+    model = await get_setting(user_id, "background_model", Config.OLLAMA_BACKGROUND_MODEL)
+
+    try:
+        output = (await generate_completion(
+            [
+                {"role": "system", "content": SYSTEM_PROMPT},
+                {"role": "user", "content": transcript},
+            ],
+            model,
+        )).strip()
+    except Exception:
+        logger.warning("closeout LLM failed for user %d", user_id, exc_info=True)
+        return
+
+    if not output or "(nothing to note)" in output.lower():
+        logger.debug("closeout: nothing to note for user %d", user_id)
+        return
+
+    await append_observations(user_id, output)
+    logger.info("closeout: appended observations for user %d (%s)", user_id, yesterday)

src/fabledassistant/services/journal_pipeline.py

@@ -18,10 +18,12 @@ from fabledassistant.services.user_profile import build_profile_context
 
 JOURNAL_PERSONA = (
     "You are the user's assistant. They've opened their journal — a day-anchored "
-    "conversation surface where they record their day. Behave like the rest of "
-    "the app's chat: respond conversationally, ask follow-up questions about what "
-    "they just said, verify details from earlier in the conversation when "
-    "relevant, and use tools naturally to act on their behalf when it makes sense. "
+    "conversation surface where they record their day. Your primary job is to "
+    "CAPTURE what they share, not to advise on it. Treat journal mode as a quiet "
+    "thinking-companion surface: record the beat, optionally ask one short "
+    "follow-up that doesn't presume they want help, and let the user lead. "
+    "Use tools to act on their behalf when they ask, not when you think they "
+    "might find it useful. "
     "The day's prep message at the top of the conversation is your context — "
     "build on it, don't restate it."
 )
@@ -57,6 +59,35 @@ these beats; if you skip the call, the beat is lost.
 Multiple distinct beats in one message → multiple record_moment calls,
 one per beat.
 
+MOMENT PHRASING — write it the way the user would jot it themselves.
+First-person or imperative, never third-person observer voice.
+  - GOOD: "Restaging Docker on the Bedford swarm; one Windows node had
+    network breakage."
+  - GOOD: "Appointment this Friday — details TBD."
+  - GOOD: "Coffee with Sarah; she's hiring."
+  - BAD: "The user mentioned having an appointment this Friday but
+    hasn't provided details yet."
+  - BAD: "User reports Docker swarm restage in progress."
+Strip "the user…" / "user mentioned…" / "user is…" framings entirely.
+
+MOMENT ENTITY LINKING — be conservative.
+  - Only attach a `task_titles` link when the user *explicitly references
+    that task* in the message. Do NOT link to a task just because it's
+    in the prep context or the only task currently open.
+  - Only attach `place_names` you can ground in something the user
+    actually said. Generic placeholders like "work" / "home" / "office"
+    are NOT places — drop them and let the user name the real one if it
+    matters.
+
+EXISTING WORK — search before recording.
+  - If the user describes ongoing or completed work that references a specific
+    project or task by name or partial name (e.g. "the sebring task",
+    "continuing on the AT&T circuit", "finished the auth refactor"), CALL
+    search_notes FIRST to locate the existing task. Update its status or log
+    work on it instead of recording a new moment when an obvious match exists.
+  - Only call record_moment for that beat if no matching task surfaces and the
+    user confirms they want a moment recorded.
+
 WHEN LINKING ENTITIES: use the *_names parameters (person_names,
 place_names, task_titles, note_titles). Server resolves them to IDs by
 lookup. Do NOT pass *_ids unless you have an exact ID returned from
@@ -89,6 +120,15 @@ RESPONSE STYLE:
 - Don't repeat a prior reply verbatim. If the user circles back on a theme,
   pick a specific concrete detail from the new message to react to.
 - Match the user's length. Short message → short reply. Don't pad.
+- DON'T offer troubleshooting steps, checklists, or generic process advice
+  for the user's work unless they explicitly ask. When the user is logging
+  what they're doing, they want to be heard, not coached. A statement like
+  "I'm prepping for an ISP migration" should be acknowledged and recorded —
+  not met with "Are you handling the network configuration yourself? Are
+  there checks you need to do first?" If a follow-up would presume they
+  want help, drop it.
+- No emojis. The journal is a thinking-companion surface; emojis read as
+  chat-bot warmth that's out of register.
 """
 
 PHASE_GREETINGS = {
@@ -134,7 +174,11 @@ async def build_journal_system_prompt(
     static_block = f"{JOURNAL_PERSONA}\n\n{JOURNAL_CALIBRATION}"
 
     today_iso = day_date.isoformat()
-    tz_block = f"Today is {today_iso} ({user_timezone})."
+    # Include the day-of-week explicitly. LLMs are unreliable at deriving
+    # weekday names from ISO dates, which causes "this Friday" / "next
+    # Monday" to land on the wrong calendar day.
+    weekday = day_date.strftime("%A")
+    tz_block = f"Today is {weekday}, {today_iso} ({user_timezone})."
 
     profile_context = await build_profile_context(user_id)
     profile_section = f"\n\n{profile_context}" if profile_context else ""

src/fabledassistant/services/journal_prep.py

@@ -23,6 +23,7 @@ from __future__ import annotations
 
 import datetime
 import logging
+from zoneinfo import ZoneInfo
 
 from sqlalchemy import select
 
@@ -38,6 +39,65 @@ from fabledassistant.services.weather import get_cached_weather_rows
 logger = logging.getLogger(__name__)
 
 
+# How many days out from today an event needs to be before the prep treats
+# it as too far-future to surface. Catches recurring-event canonical rows
+# whose RRULE expansion missed (an `rrulestr` failure falls back to the
+# canonical event in `list_events`, which leaks far-future occurrences
+# into today's prep).
+_EVENT_PROXIMITY_DAYS = 7
+
+
+def _task_to_prep_dict(task, today: datetime.date) -> dict:
+    """Render a Note row as a prep-payload task entry, tagging overdue
+    staleness when relevant so the prompt can frame it correctly."""
+    d = {
+        "id": task.id,
+        "title": task.title,
+        "status": task.status,
+        "priority": task.priority,
+        "due_date": task.due_date.isoformat() if task.due_date else None,
+    }
+    if task.due_date and task.due_date < today:
+        d["days_overdue"] = (today - task.due_date).days
+    return d
+
+
+def _filter_proximate_events(
+    events: list[dict], *, day_date: datetime.date, user_tz: ZoneInfo
+) -> list[dict]:
+    """Drop events whose start_dt is more than ``_EVENT_PROXIMITY_DAYS``
+    away from ``day_date`` in the user's local timezone.
+
+    Belt-and-suspenders against `list_events` returning a canonical
+    far-future event (e.g. when RRULE expansion fails and the loop falls
+    back to the original event row, regardless of date). The user
+    observed "Birthday — 2026-09-29 (FREQ=YEARLY)" surfacing in every
+    daily prep 5 months out; this filter keeps the prep proximate.
+    """
+    proximate: list[dict] = []
+    for e in events:
+        raw = e.get("start_dt") or ""
+        try:
+            start_dt = datetime.datetime.fromisoformat(
+                raw.replace("Z", "+00:00") if isinstance(raw, str) else ""
+            )
+            local_date = start_dt.astimezone(user_tz).date()
+            delta = abs((local_date - day_date).days)
+        except (ValueError, TypeError, AttributeError):
+            # Unparseable date — keep the event rather than suppress real data.
+            proximate.append(e)
+            continue
+        if delta <= _EVENT_PROXIMITY_DAYS:
+            proximate.append(e)
+        else:
+            logger.info(
+                "daily_prep: dropping non-proximate event %r start_local=%s "
+                "(%d days from day %s)",
+                e.get("title"), local_date.isoformat(), delta, day_date.isoformat(),
+            )
+    return proximate
+
+
 async def gather_daily_sections(
     *,
     user_id: int,
@@ -48,47 +108,85 @@ async def gather_daily_sections(
 
     Pure data fetching — no LLM call. Each section degrades to an empty
     list/dict on failure so the caller always gets a complete shape.
+
+    Tasks are returned in three explicit buckets so the prompt can frame
+    overdue items correctly (instead of calling them "due today" — the
+    pre-2026-04-29 behavior, before this rewrite).
     """
     sections: dict = {}
 
+    next_day = day_date + datetime.timedelta(days=1)
+    upcoming_end = day_date + datetime.timedelta(days=8)
     try:
-        tasks_today, _ = await list_notes(
-            user_id=user_id,
-            is_task=True,
-            status=["todo", "in_progress"],
-            due_before=day_date,
-            limit=20,
-            sort="due_date",
-            order="asc",
+        due_today_rows, _ = await list_notes(
+            user_id=user_id, is_task=True, status=["todo", "in_progress"],
+            due_after=day_date, due_before=next_day,
+            limit=20, sort="due_date", order="asc",
+        )
+        upcoming_rows, _ = await list_notes(
+            user_id=user_id, is_task=True, status=["todo", "in_progress"],
+            due_after=next_day, due_before=upcoming_end,
+            limit=20, sort="due_date", order="asc",
+        )
+        overdue_rows, _ = await list_notes(
+            user_id=user_id, is_task=True, status=["todo", "in_progress"],
+            due_before=day_date,
+            limit=20, sort="due_date", order="asc",
+        )
+        sections["tasks_due_today"] = [_task_to_prep_dict(t, day_date) for t in due_today_rows]
+        sections["tasks_upcoming"] = [_task_to_prep_dict(t, day_date) for t in upcoming_rows]
+        sections["tasks_overdue"] = [_task_to_prep_dict(t, day_date) for t in overdue_rows]
+        # Backwards-compat alias for any consumers still reading sections["tasks"].
+        # The combined view is more useful than the prior overdue-only behavior.
+        sections["tasks"] = (
+            sections["tasks_due_today"]
+            + sections["tasks_upcoming"]
+            + sections["tasks_overdue"]
         )
-        sections["tasks"] = [
-            {
-                "id": t.id,
-                "title": t.title,
-                "status": t.status,
-                "priority": t.priority,
-                "due_date": t.due_date.isoformat() if t.due_date else None,
-            }
-            for t in tasks_today
-        ]
     except Exception:
         logger.exception("daily_prep tasks section failed for user %d", user_id)
+        sections["tasks_due_today"] = []
+        sections["tasks_upcoming"] = []
+        sections["tasks_overdue"] = []
         sections["tasks"] = []
 
     try:
-        day_start = datetime.datetime.combine(day_date, datetime.time.min)
-        day_end = datetime.datetime.combine(day_date, datetime.time.max)
-        sections["events"] = await list_events(
+        try:
+            user_tz = ZoneInfo(user_timezone)
+        except Exception:
+            logger.warning("daily_prep: invalid user_timezone %r — defaulting to UTC", user_timezone)
+            user_tz = ZoneInfo("UTC")
+        # Build the local-day window in the user's TZ, then convert to UTC
+        # for the DB / RRULE expansion. A naive datetime here previously
+        # caused rrule.between() to throw, falling back to the canonical
+        # event row regardless of date — the source of stale recurring
+        # events polluting every daily prep.
+        day_start_local = datetime.datetime.combine(day_date, datetime.time.min, tzinfo=user_tz)
+        day_end_local = datetime.datetime.combine(day_date, datetime.time.max, tzinfo=user_tz)
+        day_start = day_start_local.astimezone(datetime.timezone.utc)
+        day_end = day_end_local.astimezone(datetime.timezone.utc)
+        all_events = await list_events(
             user_id=user_id,
             date_from=day_start,
             date_to=day_end,
         )
+        sections["events"] = _filter_proximate_events(
+            all_events, day_date=day_date, user_tz=user_tz,
+        )
     except Exception:
         logger.exception("daily_prep events section failed for user %d", user_id)
         sections["events"] = []
 
     try:
-        weather_rows = await get_cached_weather_rows(user_id)
+        # Lazy import: journal_scheduler imports this module for prep generation,
+        # so a top-level import would cycle.
+        from fabledassistant.services.journal_scheduler import get_journal_config
+        cfg = await get_journal_config(user_id)
+        valid_weather_keys = {
+            key for key, loc in (cfg.get("locations") or {}).items()
+            if isinstance(loc, dict) and loc.get("lat") is not None and loc.get("lon") is not None
+        }
+        weather_rows = await get_cached_weather_rows(user_id, valid_weather_keys)
         sections["weather"] = [w.to_dict() for w in weather_rows]
     except Exception:
         logger.exception("daily_prep weather section failed for user %d", user_id)
@@ -148,22 +246,40 @@ async def _open_threads(*, user_id: int, day_date: datetime.date) -> list[dict]:
     ]
 
 
+def _render_task_line(t: dict, *, include_due: bool, include_overdue: bool) -> str:
+    line = f"  - {t.get('title', '?')}"
+    if include_overdue and t.get("days_overdue"):
+        line += f" (due {t['due_date']}, {t['days_overdue']} days ago)"
+    elif include_due and t.get("due_date"):
+        line += f" (due {t['due_date']})"
+    if t.get("priority") and t["priority"] not in (None, "none"):
+        line += f" [{t['priority']} priority]"
+    if t.get("status") == "in_progress":
+        line += " [in progress]"
+    return line
+
+
 def _render_sections_for_prompt(sections: dict) -> str:
     """Render the gathered sections as a structured plain-text block for the LLM."""
     lines: list[str] = []
 
-    tasks = sections.get("tasks") or []
-    if tasks:
-        lines.append("TASKS (todo or in-progress):")
-        for t in tasks[:12]:
-            line = f"  - {t.get('title', '?')}"
-            if t.get("due_date"):
-                line += f" (due {t['due_date']})"
-            if t.get("priority") and t["priority"] not in (None, "none"):
-                line += f" [{t['priority']} priority]"
-            if t.get("status") == "in_progress":
-                line += " [in progress]"
-            lines.append(line)
+    due_today = sections.get("tasks_due_today") or []
+    upcoming = sections.get("tasks_upcoming") or []
+    overdue = sections.get("tasks_overdue") or []
+    if due_today:
+        lines.append("TASKS DUE TODAY:")
+        for t in due_today[:8]:
+            lines.append(_render_task_line(t, include_due=False, include_overdue=False))
+        lines.append("")
+    if upcoming:
+        lines.append("UPCOMING TASKS (next 7 days):")
+        for t in upcoming[:8]:
+            lines.append(_render_task_line(t, include_due=True, include_overdue=False))
+        lines.append("")
+    if overdue:
+        lines.append("OVERDUE TASKS (still on the list, not currently due):")
+        for t in overdue[:8]:
+            lines.append(_render_task_line(t, include_due=False, include_overdue=True))
         lines.append("")
 
     events = sections.get("events") or []
@@ -242,6 +358,12 @@ _PREP_SYSTEM_PROMPT = (
     "keep the prose factual and useful, not sentimental.\n"
     "- 4 to 7 sentences total. Tight. No padding, no flowery openings, no \"Good morning\" "
     "greetings unless the actual content warrants two clauses' worth.\n"
+    "- TASK BUCKETS — three sections may appear: TASKS DUE TODAY, UPCOMING TASKS, "
+    "OVERDUE TASKS. Lead with TASKS DUE TODAY when present. Do NOT call overdue items "
+    "\"due today\" — they aren't. When OVERDUE TASKS appears, surface it with the "
+    "staleness duration (\"still on the list 68 days\") and frame it as something to "
+    "revisit, not as today's work. If the only data is overdue, lead with it but "
+    "frame it as a backlog reminder.\n"
     "- If RECENT JOURNAL MOMENTS or OPEN THREADS are present, mention one or two BRIEFLY "
     "at the end as context — not as the lead. Skip them if nothing notable.\n"
     "- Close with one short invitation to journal: \"What's on your mind?\", "

src/fabledassistant/services/journal_scheduler.py

@@ -35,6 +35,7 @@ DEFAULT_CONFIG = {
     "day_rollover_hour": 4,
     "morning_end_hour": 12,
     "midday_end_hour": 18,
+    "closeout_enabled": True,
 }
 
 
@@ -88,30 +89,96 @@ def _run_daily_prep_threadsafe(user_id: int) -> None:
     asyncio.run_coroutine_threadsafe(_do_daily_prep(user_id), _loop)
 
 
+async def _do_closeout(user_id: int) -> None:
+    try:
+        tz_str = await get_user_timezone(user_id)
+        tz = _resolve_tz(tz_str)
+        now = datetime.datetime.now(tz)
+        # We just rolled into a new day in user-local time. The day that
+        # just ended is yesterday's calendar date regardless of whether
+        # rollover_hour is 0 or 4 — APScheduler fires precisely at the
+        # configured hour so no clock-skew correction is needed.
+        yesterday = now.date() - datetime.timedelta(days=1)
+        from fabledassistant.services.journal_closeout import run_for_user
+        await run_for_user(user_id=user_id, yesterday=yesterday)
+    except Exception:
+        logger.exception("Closeout failed for user %d", user_id)
+
+
+def _run_closeout_threadsafe(user_id: int) -> None:
+    if _loop is None:
+        return
+    asyncio.run_coroutine_threadsafe(_do_closeout(user_id), _loop)
+
+
+async def _closeout_catchup(user_id: int) -> None:
+    """On startup, run yesterday's closeout once if the slot already passed
+    and no entry for yesterday exists in observations_raw.
+    """
+    try:
+        tz_str = await get_user_timezone(user_id)
+        tz = _resolve_tz(tz_str)
+        config = await get_journal_config(user_id)
+        if not config.get("closeout_enabled", True):
+            return
+        rollover_hour = int(config.get("day_rollover_hour", 4))
+        now = datetime.datetime.now(tz)
+        # Slot hasn't passed yet today → wait for the cron.
+        if now.hour < rollover_hour:
+            return
+        yesterday = (now - datetime.timedelta(days=1)).date()
+
+        from fabledassistant.services.user_profile import get_profile
+        profile = await get_profile(user_id)
+        existing_dates = {
+            (e or {}).get("date") for e in (profile.observations_raw or [])
+        }
+        if yesterday.isoformat() in existing_dates:
+            return
+
+        from fabledassistant.services.journal_closeout import run_for_user
+        await run_for_user(user_id=user_id, yesterday=yesterday)
+    except Exception:
+        logger.exception("Closeout catch-up failed for user %d", user_id)
+
+
 async def update_user_schedule(user_id: int) -> None:
-    """Add or replace this user's daily-prep job using their current config."""
+    """Add or replace this user's daily-prep + closeout jobs from current config."""
     if _scheduler is None:
         return
-    job_id = f"journal_prep_{user_id}"
-    if _scheduler.get_job(job_id):
-        _scheduler.remove_job(job_id)
 
     config = await get_journal_config(user_id)
-    if not config.get("prep_enabled", True):
-        return
-
     tz_str = await get_user_timezone(user_id)
     tz = _resolve_tz(tz_str)
-    prep_hour = int(config.get("prep_hour", 5))
-    prep_minute = int(config.get("prep_minute", 0))
 
-    _scheduler.add_job(
-        _run_daily_prep_threadsafe,
-        trigger=CronTrigger(hour=prep_hour, minute=prep_minute, timezone=tz),
-        args=[user_id],
-        id=job_id,
-        replace_existing=True,
-    )
+    # ── Prep job ──────────────────────────────────────────────────────────
+    prep_job_id = f"journal_prep_{user_id}"
+    if _scheduler.get_job(prep_job_id):
+        _scheduler.remove_job(prep_job_id)
+    if config.get("prep_enabled", True):
+        prep_hour = int(config.get("prep_hour", 5))
+        prep_minute = int(config.get("prep_minute", 0))
+        _scheduler.add_job(
+            _run_daily_prep_threadsafe,
+            trigger=CronTrigger(hour=prep_hour, minute=prep_minute, timezone=tz),
+            args=[user_id],
+            id=prep_job_id,
+            replace_existing=True,
+        )
+
+    # ── Closeout job ──────────────────────────────────────────────────────
+    closeout_job_id = f"journal_closeout_{user_id}"
+    if _scheduler.get_job(closeout_job_id):
+        _scheduler.remove_job(closeout_job_id)
+    if config.get("closeout_enabled", True):
+        rollover_hour = int(config.get("day_rollover_hour", 4))
+        _scheduler.add_job(
+            _run_closeout_threadsafe,
+            trigger=CronTrigger(hour=rollover_hour, minute=0, timezone=tz),
+            args=[user_id],
+            id=closeout_job_id,
+            replace_existing=True,
+        )
 
 
 async def _register_all_user_jobs() -> None:
@@ -119,6 +186,9 @@ async def _register_all_user_jobs() -> None:
         users = (await session.execute(select(User))).scalars().all()
     for user in users:
         await update_user_schedule(user.id)
+        # Fire catch-up asynchronously so a slow LLM call doesn't block startup
+        if _loop is not None:
+            asyncio.run_coroutine_threadsafe(_closeout_catchup(user.id), _loop)
 
 
 def start_journal_scheduler(loop: asyncio.AbstractEventLoop) -> None:

src/fabledassistant/services/llm.py

@@ -602,7 +602,12 @@ async def build_context(
             }
 
     assistant_name = await get_setting(user_id, "assistant_name", "Fable")
-    today = date_type.today().isoformat()
+    _today_obj = date_type.today()
+    today = _today_obj.isoformat()
+    # Day-of-week paired with the ISO date so the model doesn't have to
+    # derive the weekday — that derivation is a documented failure mode
+    # for "this Friday" / "next Monday"-style requests.
+    today_weekday = _today_obj.strftime("%A")
     has_caldav = await is_caldav_configured(user_id)
 
     # Build tool usage guidance based on available integrations
@@ -615,6 +620,7 @@ async def build_context(
         "CRITICAL: Call the tool functions directly. NEVER write out function calls as text or code. NEVER describe what you would do — just do it.",
         "GROUNDING: When the user asks about their own data — tasks, notes, events, projects, news, anything stored in this system — call the relevant tool to see what actually exists before answering. Never assert facts about the user's data from memory, prior context, or assumption. If you are unsure whether something exists, check with a tool.",
         "HONESTY WHEN EMPTY: If a tool returns empty results (no matching tasks, no events in the date range, no search hits, no notes found), tell the user plainly that nothing matched. Do not fabricate example items, do not invent plausible-sounding meetings or deadlines to fill the response, and do not hedge with generic suggestions dressed up as real data. A direct 'you don't have anything on your calendar today' is always better than an invented event.",
+        "EXISTING WORK: When the user describes ongoing or completed work that references a specific project or task by name or partial name, call search_notes first to locate the existing item. Only call record_moment, create_task, or create_note if no matching task surfaces and the user confirms.",
     ]
     actions = [
         "create_note (also creates tasks — set status='todo')", "update_note", "delete_note",
@@ -678,7 +684,7 @@ async def build_context(
     entities_context = await get_people_and_places_context(user_id)
     entities_section = f"\n\n{entities_context}" if entities_context else ""
 
-    dynamic_tail = f"\n\nToday's date is {today}.{tz_line}{profile_section}{entities_section}"
+    dynamic_tail = f"\n\nToday is {today_weekday}, {today}.{tz_line}{profile_section}{entities_section}"
 
     # --- System message: stable content only ---
     # Workspace context and history summary stay here because they carry

src/fabledassistant/services/notes.py

@@ -22,6 +22,17 @@ def _normalize_tags(tags: list[str]) -> list[str]:
     return out
 
 
+# Type-nouns the LLM tends to include in search queries. Treating them as
+# required ILIKE terms drops literal-title matches; we strip them server-side
+# and let the `type` / `project` parameters scope results instead.
+_SEARCH_TYPE_NOUNS = {"task", "tasks", "note", "notes", "project", "projects"}
+
+
+def _strip_type_nouns(q: str) -> list[str]:
+    """Return q's tokens with type-nouns removed (case-insensitive)."""
+    return [t for t in q.split() if t.lower() not in _SEARCH_TYPE_NOUNS]
+
+
 async def _maybe_reactivate_project(project_id: int) -> None:
     """If a project is paused, reactivate it — activity indicates resumed work."""
     from fabledassistant.models.project import Project
@@ -155,7 +166,7 @@ async def list_notes(
             count_query = count_query.where(Note.status.is_(None))
 
         if q:
-            terms = q.split()
+            terms = _strip_type_nouns(q)
             for term in terms:
                 escaped_term = term.replace("\\", "\\\\").replace("%", "\\%").replace("_", "\\_")
                 pattern = f"%{escaped_term}%"

src/fabledassistant/services/tools/_helpers.py

@@ -22,31 +22,71 @@ def schedule_embedding(note_id: int, user_id: int, title: str, body: str) -> Non
         asyncio.create_task(upsert_note_embedding(note_id, user_id, text))
 
 
+_PROJECT_QUERY_NOISE = {"project", "projects"}
+
+
+def _normalize(s: str) -> str:
+    """Lowercase and collapse non-alphanumerics to single spaces."""
+    return re.sub(r"[^a-z0-9]+", " ", s.lower()).strip()
+
+
+def _normalize_query(query: str) -> str:
+    """Normalize plus drop trailing type-nouns ('project' / 'projects')
+    that users add as filler when referring to a project by name."""
+    tokens = [t for t in _normalize(query).split() if t not in _PROJECT_QUERY_NOISE]
+    return " ".join(tokens)
+
+
+def score_project_match(query: str, project) -> float:
+    """Score how well `query` matches `project`. Range [0.0, 1.0].
+
+    Tiered: exact title → 1.0, substring either-way → 0.85, query found in
+    description/summary → 0.70, otherwise SequenceMatcher ratio against the
+    title. Substring tiers exist because LLM-generated colloquial queries
+    (e.g. "famous supply project" for "Famous-Supply Work topics") would
+    otherwise score too low under pure SequenceMatcher and be treated as
+    no match. Filler words like "project" are stripped from the query so
+    the substring check still fires.
+    """
+    q = _normalize_query(query)
+    if not q:
+        return 0.0
+    title = _normalize(project.title)
+    description = _normalize(project.description or "")
+    summary = _normalize(project.auto_summary or "")
+    combined = f"{title} {description} {summary}".strip()
+
+    if q == title:
+        return 1.0
+    if q in title or title in q:
+        return 0.85
+    if q in combined:
+        return 0.70
+    # SequenceMatcher against the title — comparing against `combined`
+    # dilutes the ratio with long description/summary text and produces
+    # uniformly low scores even for plausible matches.
+    return SequenceMatcher(None, q, title).ratio()
+
+
 async def resolve_project(user_id: int, project_name: str):
-    """Exact-then-fuzzy project lookup. Returns the Project or None.
+    """Exact-then-scored project lookup. Returns the Project or None.
 
     Resolution order:
-    1. Exact title match (case-insensitive via DB)
-    2. project_name is a substring of an existing title
-    3. Existing title is a substring of project_name
-    4. SequenceMatcher ratio >= 0.55
+    1. Exact title match (case-insensitive via DB query).
+    2. Highest `score_project_match` across all projects, threshold 0.55.
     """
     from fabledassistant.services.projects import get_project_by_title, list_projects
 
     proj = await get_project_by_title(user_id, project_name)
     if proj is not None:
         return proj
-    needle = project_name.lower().strip()
+
     all_p = await list_projects(user_id)
+    best, best_score = None, 0.0
     for p in all_p:
-        haystack = p.title.lower().strip()
-        if needle in haystack or haystack in needle:
-            return p
-    best, best_r = None, 0.0
-    for p in all_p:
-        r = SequenceMatcher(None, needle, p.title.lower().strip()).ratio()
-        if r >= 0.55 and r > best_r:
-            best, best_r = p, r
+        score = score_project_match(project_name, p)
+        if score >= 0.55 and score > best_score:
+            best, best_score = p, score
     return best
 
 

src/fabledassistant/services/tools/calendar.py

@@ -2,7 +2,8 @@
 
 from __future__ import annotations
 
-from datetime import datetime, timezone
+import re
+from datetime import date as _date, datetime, time as _time, timezone
 
 from fabledassistant.services.events import (
     create_event as events_create_event,
@@ -17,10 +18,49 @@ from fabledassistant.services.tools._registry import tool
 from fabledassistant.services.tz import get_user_tz
 
 
+_DATE_RE = re.compile(r"^\d{4}-\d{2}-\d{2}$")
+_TIME_RE = re.compile(r"^\d{2}:\d{2}(:\d{2})?$")
+
+
+async def _combine_local_in_user_tz(
+    user_id: int, date_str: str, time_str: str | None
+) -> datetime:
+    """Build a UTC datetime from separate date and time strings.
+
+    The whole point of this helper: a `YYYY-MM-DD` string carries no TZ
+    metadata that a model could mis-tag, so the calendar day cannot drift
+    across the local→UTC boundary. The wall-clock `HH:MM` likewise has no
+    TZ; we attach the user's local zone explicitly via ``datetime.combine``
+    and then convert to UTC for storage.
+
+    Strict shape validation rejects anything that isn't a bare date or a
+    bare time — no `2026-05-01Z`, no `08:00 UTC` slipping through.
+    """
+    if not _DATE_RE.match(date_str):
+        raise ValueError(
+            f"start_date / end_date must be YYYY-MM-DD with no timezone; got {date_str!r}"
+        )
+    d = _date.fromisoformat(date_str)
+    if time_str is None or time_str == "":
+        t = _time(0, 0)
+    else:
+        if not _TIME_RE.match(time_str):
+            raise ValueError(
+                f"start_time / end_time must be HH:MM (or HH:MM:SS), no timezone; got {time_str!r}"
+            )
+        t = _time.fromisoformat(time_str)
+    user_tz = await get_user_tz(user_id)
+    local = datetime.combine(d, t, tzinfo=user_tz)
+    return local.astimezone(timezone.utc)
+
+
 async def _parse_datetime_in_user_tz(
     user_id: int, value: str
 ) -> tuple[datetime, bool]:
-    """Parse a date/datetime string from the model into a UTC-aware datetime.
+    """Legacy single-string parser. Kept as a fallback when the model
+    emits the older `start` / `end` shape; new calls should use
+    `start_date`+`start_time` (and `end_date`+`end_time`) which sidestep
+    the TZ-tagging foot-gun this parser is vulnerable to.
 
     Naive inputs are interpreted in the **user's local timezone** and then
     converted to UTC for storage. Never default to UTC for naive inputs —
@@ -38,14 +78,178 @@ async def _parse_datetime_in_user_tz(
     return dt.astimezone(timezone.utc), was_date_only
 
 
+async def _resolve_event_start(
+    user_id: int, args: dict
+) -> tuple[datetime, bool]:
+    """Resolve the start datetime from either the new split fields
+    (`start_date` + optional `start_time`) or the legacy combined `start`.
+    Returns ``(utc_datetime, was_date_only)``."""
+    if "start_date" in args and args["start_date"]:
+        date_str = args["start_date"]
+        time_str = args.get("start_time") or None
+        return await _combine_local_in_user_tz(user_id, date_str, time_str), time_str is None
+    if "start" in args and args["start"]:
+        return await _parse_datetime_in_user_tz(user_id, args["start"])
+    raise ValueError("Either start_date or start is required")
+
+
+async def _resolve_event_end(
+    user_id: int, args: dict
+) -> datetime | None:
+    """Resolve the end datetime from either the new split fields or the
+    legacy combined `end`. Returns ``None`` when no end fields are set."""
+    if "end_date" in args and args["end_date"]:
+        date_str = args["end_date"]
+        time_str = args.get("end_time") or None
+        return await _combine_local_in_user_tz(user_id, date_str, time_str)
+    if "end" in args and args["end"]:
+        dt, _ = await _parse_datetime_in_user_tz(user_id, args["end"])
+        return dt
+    return None
+
+
+def _candidate_summary(event) -> dict:
+    """Compact event summary used in ambiguous-match responses.
+
+    Keeps the candidate list small so the model can disambiguate from
+    the same turn without bloating context. Includes id (for the
+    follow-up call), title, start_dt, and location when present.
+    """
+    return {
+        "id": event.id,
+        "title": event.title,
+        "start_dt": event.start_dt.isoformat() if event.start_dt else None,
+        "location": event.location or None,
+    }
+
+
+async def _resolve_event_for_action(
+    *, user_id: int, arguments: dict, action: str,
+):
+    """Pick the single event the model intends to update or delete.
+
+    Resolution rules:
+      - ``event_id`` in arguments → exact lookup (skip query). Used by
+        the model to disambiguate after a multi-match refusal.
+      - else ``query`` → ``find_events_by_query``:
+          - 0 results → return error tuple ("not_found", ...)
+          - 1 result → return that event
+          - 2+ results → return ("ambiguous", error, candidates) so the
+            caller can refuse the call and show candidates to the model.
+
+    Returns either an Event (success) or a 2- or 3-tuple of
+    ``(error_kind, error_dict)`` for the caller to translate into a
+    tool-call response.
+    """
+    from fabledassistant.services.events import get_event
+
+    event_id = arguments.get("event_id")
+    if event_id is not None:
+        try:
+            event_id_int = int(event_id)
+        except (TypeError, ValueError):
+            return ("invalid_id", {
+                "success": False,
+                "error": f"event_id must be an integer; got {event_id!r}.",
+            })
+        ev = await get_event(user_id=user_id, event_id=event_id_int)
+        if ev is None:
+            return ("not_found", {
+                "success": False,
+                "error": f"No event found with id={event_id_int}.",
+            })
+        return ev
+
+    query = arguments.get("query", "")
+    if not query:
+        return ("invalid_query", {
+            "success": False,
+            "error": "Either query or event_id is required.",
+        })
+    matches = await find_events_by_query(user_id=user_id, query=query)
+    if not matches:
+        return ("not_found", {
+            "success": False,
+            "error": f"No event found matching {query!r}.",
+        })
+    if len(matches) == 1:
+        return matches[0]
+    # Multi-match: refuse and surface candidates so the model can
+    # disambiguate via event_id on the next call. Prevents the silent-
+    # picks-matches[0] failure mode that mutated the wrong event in the
+    # 2026-04-29 dentist-appointment incident (Fable #161).
+    return ("ambiguous", {
+        "success": False,
+        "error": (
+            f"Found {len(matches)} events matching {query!r}. "
+            f"Pick one by passing `event_id` instead of `query`, "
+            f"or refine the search term to match a single event."
+        ),
+        "action": action,
+        "candidates": [_candidate_summary(m) for m in matches[:8]],
+    })
+
+
+def _validate_weekday(start_dt_utc: datetime, user_tz, expected: str | None) -> str | None:
+    """Verify the resolved local date falls on the expected day of the week.
+
+    Models routinely miscompute "this Friday" / "next Monday" when the
+    system prompt only carries an ISO date without a weekday. When the
+    model passes `expected_weekday`, the backend rejects mismatches with
+    a self-correcting error message naming the actual weekday.
+
+    Returns an error string on mismatch, or ``None`` when the check
+    passes (or no expected weekday was supplied).
+    """
+    if not expected:
+        return None
+    expected_norm = expected.strip().lower()
+    valid = {"monday", "tuesday", "wednesday", "thursday", "friday", "saturday", "sunday"}
+    if expected_norm not in valid:
+        return f"expected_weekday must be a full English weekday name; got {expected!r}."
+    local = start_dt_utc.astimezone(user_tz)
+    actual = local.strftime("%A").lower()
+    if actual == expected_norm:
+        return None
+    return (
+        f"Date {local.date().isoformat()} falls on {actual.title()}, "
+        f"not {expected_norm.title()}. Recompute the date for "
+        f"{expected_norm.title()} or confirm with the user before retrying."
+    )
+
+
 @tool(
     name="create_event",
-    description="Create a calendar event for the user. Use this when the user asks to schedule, add, or create a meeting, appointment, or event. Pass dates and datetimes in the user's local time — a bare date like '2026-09-30' is interpreted as that day in the user's configured timezone.",
+    description=(
+        "Create a calendar event for the user. Use this when the user asks "
+        "to schedule, add, or create a meeting, appointment, or event. "
+        "Always pass `start_date` (YYYY-MM-DD) and `start_time` (HH:MM) as "
+        "separate fields in the user's local time — never combine them and "
+        "never include a timezone suffix. The server attaches the user's "
+        "configured timezone. Omit `start_time` (or set `all_day=true`) "
+        "for all-day events like birthdays or holidays. "
+        "When the user names a weekday ('this Friday', 'next Monday'), "
+        "state the resolved calendar date in your reply BEFORE calling "
+        "this tool, and pass `expected_weekday` so the server can verify "
+        "the date falls on the day you intended.\n\n"
+        "DON'T call this tool with placeholder values. If the user "
+        "mentions an event without giving you concrete details (a real "
+        "title, a specific time, and location when it applies), record "
+        "a moment instead and ask for the missing pieces — do NOT create "
+        "an event with a stand-in title like 'Appointment', 'Meeting', "
+        "or 'Event' and a description that says 'details TBD'. Wait for "
+        "the user's reply, then call create_event ONCE with the actual "
+        "title, time, and location. Premature placeholder events pollute "
+        "the calendar and require an immediate update_event to fix — "
+        "both visible to the user, neither what they asked for."
+    ),
     parameters={
         "title": {"type": "string", "description": "A descriptive event title"},
-        "start": {"type": "string", "description": "Start date (YYYY-MM-DD) or datetime (YYYY-MM-DDTHH:MM) in the user's local time. Include a timezone offset only if the user explicitly mentions one."},
-        "end": {"type": "string", "description": "Optional end date or datetime in the user's local time"},
-        "duration": {"type": "integer", "description": "Optional duration in minutes (default 60, ignored if end is set or all_day is true)"},
+        "start_date": {"type": "string", "description": "Start calendar date as YYYY-MM-DD in the user's local time. No timezone suffix."},
+        "start_time": {"type": "string", "description": "Start wall-clock time as HH:MM (24-hour). Omit for all-day events. No timezone suffix."},
+        "end_date": {"type": "string", "description": "Optional end calendar date as YYYY-MM-DD."},
+        "end_time": {"type": "string", "description": "Optional end wall-clock time as HH:MM."},
+        "duration": {"type": "integer", "description": "Optional duration in minutes (default 60, ignored if end_date/end_time is set or all_day is true)"},
         "description": {"type": "string", "description": "Optional event description"},
         "location": {"type": "string", "description": "Optional event location"},
         "color": {"type": "string", "description": "Optional hex color for the event (e.g. '#6366f1')"},
@@ -55,30 +259,36 @@ async def _parse_datetime_in_user_tz(
         "attendees": {"type": "array", "items": {"type": "string"}, "description": "Optional list of attendee email addresses"},
         "calendar_name": {"type": "string", "description": "Optional calendar name to create the event in. Falls back to default calendar."},
         "project": {"type": "string", "description": "Optional project name to associate this event with"},
+        "expected_weekday": {"type": "string", "description": "Optional weekday name (e.g. 'friday') the start_date should fall on. Pass this whenever the user names a weekday so the server can verify the date is correct. Rejects with a corrective error if the date falls on a different day."},
+        # Legacy combined fields kept for backward compatibility with saved
+        # tool-call payloads in conversation history. New calls should use
+        # start_date + start_time. Hidden from typical model output via the
+        # description above; still accepted by the resolver as a fallback.
+        "start": {"type": "string", "description": "[Deprecated] Combined start datetime — prefer start_date + start_time."},
+        "end": {"type": "string", "description": "[Deprecated] Combined end datetime — prefer end_date + end_time."},
     },
-    required=["title", "start"],
+    required=["title"],
 )
 async def create_event_tool(*, user_id, arguments, **_ctx):
-    start_str = arguments["start"]
-    end_str = arguments.get("end")
     all_day = arguments.get("all_day", False)
     try:
-        # Naive dates/datetimes are interpreted in the user's local
-        # timezone, not UTC. Storing UTC for naive inputs caused all-day
-        # events to land on the previous day for negative-offset users.
-        start_dt, start_was_date_only = await _parse_datetime_in_user_tz(
-            user_id, start_str
-        )
-    except (ValueError, TypeError):
-        return {"success": False, "error": f"Invalid start datetime: {start_str!r}"}
+        start_dt, start_was_date_only = await _resolve_event_start(user_id, arguments)
+    except ValueError as exc:
+        return {"success": False, "error": str(exc)}
+    except TypeError as exc:
+        return {"success": False, "error": f"Invalid start: {exc}"}
     if start_was_date_only:
         all_day = True
-    end_dt = None
-    if end_str:
-        try:
-            end_dt, _ = await _parse_datetime_in_user_tz(user_id, end_str)
-        except (ValueError, TypeError):
-            return {"success": False, "error": f"Invalid end datetime: {end_str!r}"}
+    user_tz = await get_user_tz(user_id)
+    weekday_err = _validate_weekday(start_dt, user_tz, arguments.get("expected_weekday"))
+    if weekday_err:
+        return {"success": False, "error": weekday_err}
+    try:
+        end_dt = await _resolve_event_end(user_id, arguments)
+    except ValueError as exc:
+        return {"success": False, "error": str(exc)}
+    except TypeError as exc:
+        return {"success": False, "error": f"Invalid end: {exc}"}
     project_id = None
     project_name = arguments.get("project")
     if project_name:
@@ -168,27 +378,51 @@ async def search_events_tool(*, user_id, arguments, **_ctx):
 
 @tool(
     name="update_event",
-    description="Update an existing calendar event. Use this when the user asks to change, move, reschedule, or modify an event.",
+    description=(
+        "Update an existing calendar event. Use this when the user asks to "
+        "change, move, reschedule, or modify an event. Pass `start_date` "
+        "(YYYY-MM-DD) and `start_time` (HH:MM) as separate fields in the "
+        "user's local time when rescheduling — never combine them, never "
+        "include a timezone suffix. "
+        "When the user names a weekday ('move to Friday'), state the "
+        "resolved calendar date in your reply BEFORE calling this tool, "
+        "and pass `expected_weekday` so the server can verify the date "
+        "falls on the day you intended.\n\n"
+        "Identify the event with EITHER `query` (a title substring) OR "
+        "`event_id` (when you already have an exact id from a prior tool "
+        "result). If `query` matches multiple events, the tool returns "
+        "an ambiguity error with a candidate list — pick one by passing "
+        "its `event_id` on the next call, or refine the query so it "
+        "matches a single event."
+    ),
     parameters={
-        "query": {"type": "string", "description": "Search term to find the event to update (matches against title)"},
+        "query": {"type": "string", "description": "Search term to find the event to update (matches against title). Required unless event_id is set."},
+        "event_id": {"type": "integer", "description": "Exact event id, used to disambiguate when a prior call returned multiple candidates. Takes precedence over query."},
         "title": {"type": "string", "description": "New title for the event"},
-        "start": {"type": "string", "description": "New start datetime in ISO 8601 format"},
-        "end": {"type": "string", "description": "New end datetime in ISO 8601 format"},
+        "start_date": {"type": "string", "description": "New start calendar date as YYYY-MM-DD in the user's local time. No timezone suffix."},
+        "start_time": {"type": "string", "description": "New start wall-clock time as HH:MM. No timezone suffix."},
+        "end_date": {"type": "string", "description": "New end calendar date as YYYY-MM-DD."},
+        "end_time": {"type": "string", "description": "New end wall-clock time as HH:MM."},
         "all_day": {"type": "boolean", "description": "Whether the event is all-day"},
         "description": {"type": "string", "description": "New event description"},
         "location": {"type": "string", "description": "New event location"},
         "color": {"type": "string", "description": "New hex color for the event (e.g. '#6366f1')"},
         "recurrence": {"type": "string", "description": "New iCalendar RRULE"},
         "reminder_minutes": {"type": "integer", "description": "Reminder N minutes before the event. Pass 0 to remove an existing reminder."},
+        "expected_weekday": {"type": "string", "description": "Optional weekday name (e.g. 'friday') the new start_date should fall on. Pass whenever the user names a weekday."},
+        # Legacy combined fields kept for backcompat — see create_event.
+        "start": {"type": "string", "description": "[Deprecated] Combined start datetime — prefer start_date + start_time."},
+        "end": {"type": "string", "description": "[Deprecated] Combined end datetime — prefer end_date + end_time."},
     },
-    required=["query"],
+    required=[],
 )
 async def update_event_tool(*, user_id, arguments, **_ctx):
-    query = arguments.get("query", "")
-    matches = await find_events_by_query(user_id=user_id, query=query)
-    if not matches:
-        return {"success": False, "error": f"No event found matching '{query}'."}
-    event_to_update = matches[0]
+    resolved = await _resolve_event_for_action(
+        user_id=user_id, arguments=arguments, action="update",
+    )
+    if isinstance(resolved, tuple):
+        return resolved[1]  # error dict from the resolver
+    event_to_update = resolved
     fields: dict = {}
     for str_field in ("title", "description", "location", "color", "recurrence"):
         if arguments.get(str_field) is not None:
@@ -198,16 +432,24 @@ async def update_event_tool(*, user_id, arguments, **_ctx):
     if "reminder_minutes" in arguments:
         rm = arguments["reminder_minutes"]
         fields["reminder_minutes"] = None if rm == 0 else rm
-    for dt_field, key in (("start_dt", "start"), ("end_dt", "end")):
-        val = arguments.get(key)
-        if val:
-            try:
-                # Naive datetimes are user-local, not UTC — see
-                # ``_parse_datetime_in_user_tz`` docstring.
-                dt, _ = await _parse_datetime_in_user_tz(user_id, val)
-                fields[dt_field] = dt
-            except (ValueError, TypeError):
-                return {"success": False, "error": f"Invalid datetime for {key}: {val!r}"}
+    # Resolve start: split fields preferred, legacy `start` as fallback.
+    if arguments.get("start_date") or arguments.get("start"):
+        try:
+            start_dt, _ = await _resolve_event_start(user_id, arguments)
+        except (ValueError, TypeError) as exc:
+            return {"success": False, "error": f"Invalid start: {exc}"}
+        user_tz = await get_user_tz(user_id)
+        weekday_err = _validate_weekday(start_dt, user_tz, arguments.get("expected_weekday"))
+        if weekday_err:
+            return {"success": False, "error": weekday_err}
+        fields["start_dt"] = start_dt
+    if arguments.get("end_date") or arguments.get("end"):
+        try:
+            end_dt = await _resolve_event_end(user_id, arguments)
+        except (ValueError, TypeError) as exc:
+            return {"success": False, "error": f"Invalid end: {exc}"}
+        if end_dt is not None:
+            fields["end_dt"] = end_dt
     updated = await events_update_event(user_id=user_id, event_id=event_to_update.id, **fields)
     if updated is None:
         return {"success": False, "error": "Event not found or update failed."}
@@ -216,18 +458,29 @@ async def update_event_tool(*, user_id, arguments, **_ctx):
 
 @tool(
     name="delete_event",
-    description="Delete a calendar event. Use this when the user asks to cancel, remove, or delete an event.",
+    description=(
+        "Delete a calendar event. Use this when the user asks to cancel, "
+        "remove, or delete an event. Identify the event with EITHER "
+        "`query` (a title substring) OR `event_id` (when you have an "
+        "exact id). If `query` matches multiple events, the tool returns "
+        "an ambiguity error with a candidate list — pick one by passing "
+        "its `event_id` on the next call, or refine the query so it "
+        "matches a single event. Deleting the wrong event is a costly "
+        "user error; never guess between candidates."
+    ),
     parameters={
-        "query": {"type": "string", "description": "Search term to find the event to delete (matches against title)"},
+        "query": {"type": "string", "description": "Search term to find the event to delete (matches against title). Required unless event_id is set."},
+        "event_id": {"type": "integer", "description": "Exact event id, used to disambiguate when a prior call returned multiple candidates. Takes precedence over query."},
     },
-    required=["query"],
+    required=[],
 )
 async def delete_event_tool(*, user_id, arguments, **_ctx):
-    query = arguments.get("query", "")
-    matches = await find_events_by_query(user_id=user_id, query=query)
-    if not matches:
-        return {"success": False, "error": f"No event found matching '{query}'."}
-    event_to_delete = matches[0]
+    resolved = await _resolve_event_for_action(
+        user_id=user_id, arguments=arguments, action="delete",
+    )
+    if isinstance(resolved, tuple):
+        return resolved[1]
+    event_to_delete = resolved
     await events_delete_event(user_id=user_id, event_id=event_to_delete.id)
     return {"success": True, "type": "event_deleted", "data": {"id": event_to_delete.id, "title": event_to_delete.title}}
 

src/fabledassistant/services/tools/journal.py

@@ -3,6 +3,7 @@ from __future__ import annotations
 
 import datetime
 import logging
+import re
 from typing import Any
 
 from sqlalchemy import func, select
@@ -15,6 +16,97 @@ from fabledassistant.services.tools._registry import tool
 logger = logging.getLogger(__name__)
 
 
+# Generic placeholders the model occasionally emits for `place_names` when no
+# real place was named. Filtered out server-side as belt-and-suspenders to the
+# prompt-layer guidance — these aren't places, just role-labels for locations
+# the user already has named (Home / Work weather targets, etc.).
+_PLACEHOLDER_PLACE_NAMES = frozenset({
+    "work", "home", "office", "the office", "my office", "my work",
+    "my home", "house", "my house", "the house",
+})
+
+# Short closed-class words excluded from the keyword-overlap check below.
+# Case is normalized to lowercase before comparison.
+_STOPWORDS = frozenset({
+    "the", "a", "an", "and", "or", "but", "at", "in", "on", "of", "to",
+    "for", "with", "by", "from", "about", "as", "is", "was", "were", "be",
+    "been", "being", "have", "has", "had", "do", "does", "did", "will",
+    "would", "could", "should", "may", "might", "must", "this", "that",
+    "these", "those", "i", "you", "he", "she", "we", "they", "it", "his",
+    "her", "their", "my", "your", "our", "its", "me", "him", "us", "them",
+    "are", "if", "so", "no", "not", "yes", "now", "then", "than", "too",
+    "very", "just", "also", "any", "all", "some", "one", "two", "out",
+    "up", "down", "off", "over", "under", "into", "onto", "upon",
+})
+
+
+def _content_keywords(text: str) -> set[str]:
+    """Tokenize text into the meaningful keyword set used for overlap checks.
+
+    Lowercased, alphanumeric runs only, stopwords removed, tokens shorter
+    than 3 chars dropped. Numeric tokens are kept (e.g. "Branch 14" yields
+    {"branch", "14"}) because they often anchor task references.
+    """
+    tokens = re.split(r"[^a-z0-9]+", text.lower())
+    return {t for t in tokens if len(t) >= 3 and t not in _STOPWORDS}
+
+
+def _filter_placeholder_places(names: list[str]) -> tuple[list[str], list[str]]:
+    """Drop generic placeholders from a `place_names` list.
+
+    Returns ``(kept, dropped)``. The dropped list is used purely for log
+    visibility — the moment is still created, the bogus links are just
+    not persisted.
+    """
+    kept: list[str] = []
+    dropped: list[str] = []
+    for n in names:
+        norm = (n or "").strip()
+        if norm and norm.lower() in _PLACEHOLDER_PLACE_NAMES:
+            dropped.append(norm)
+        else:
+            kept.append(norm)
+    return kept, dropped
+
+
+async def _filter_task_ids_by_keyword_overlap(
+    *, user_id: int, content: str, task_ids: list[int]
+) -> list[int]:
+    """Drop task links whose title shares no meaningful keyword with the
+    moment content.
+
+    Reproducer this guards against (2026-04-27): the model emitted
+    `task_titles=["Research Weston's ADHD Evaluation"]` on a moment about
+    restaging Docker — the title was real (Weston's task is in the prep
+    context) but the user never referenced it. Without this guard, the
+    only task surfaced in the prep gets attached to every moment as
+    filler. After this guard the link is dropped (zero-overlap) and a
+    log entry is emitted at INFO so we can observe how often this fires.
+    """
+    if not task_ids:
+        return []
+    async with async_session() as session:
+        stmt = select(Note.id, Note.title).where(
+            Note.user_id == user_id,
+            Note.id.in_(task_ids),
+        )
+        rows = (await session.execute(stmt)).all()
+    title_by_id = {nid: (title or "") for nid, title in rows}
+    content_kw = _content_keywords(content)
+    kept: list[int] = []
+    for tid in task_ids:
+        title = title_by_id.get(tid, "")
+        title_kw = _content_keywords(title)
+        if title_kw and content_kw & title_kw:
+            kept.append(tid)
+        else:
+            logger.info(
+                "record_moment: dropped task link id=%s title=%r — no keyword overlap with content %r",
+                tid, title, content[:80],
+            )
+    return kept
+
+
 async def _resolve_entity_ids_by_name(
     *,
     user_id: int,
@@ -73,12 +165,25 @@ async def _resolve_entity_ids_by_name(
         "STRONGLY PREFER the *_names parameters when linking entities — the server "
         "resolves names to IDs by lookup, so you cannot accidentally invent or "
         "re-use the wrong ID. Use *_ids only when you have an exact ID returned "
-        "from another tool call in this same turn."
+        "from another tool call in this same turn. "
+        "`task_titles` and `note_titles` must be exact titles returned by a prior "
+        "search_notes call in this same turn. Do NOT pass user-typed phrases, "
+        "project names, or invented titles. If you have not searched yet, call "
+        "search_notes first."
     ),
     parameters={
         "content": {
             "type": "string",
-            "description": "1-2 sentence distillation of the moment in the user's voice or third-person.",
+            "description": (
+                "1-2 sentence distillation of the moment in the user's "
+                "voice — first-person or imperative, like a journal jot. "
+                "GOOD: 'Restaging Docker on the Bedford swarm; one "
+                "Windows node had network breakage.' / 'Appointment "
+                "Friday — details TBD.' "
+                "BAD: 'The user mentioned having an appointment.' / "
+                "'User reports Docker swarm restage.' Strip 'the user…' "
+                "/ 'user mentioned…' framings entirely."
+            ),
         },
         "occurred_at": {
             "type": "string",
@@ -171,10 +276,17 @@ async def record_moment_tool(*, user_id, arguments, conv_id=None, **_ctx):
             note_type="person",
         )
     )
+    raw_place_names = arguments.get("place_names") or []
+    kept_place_names, dropped_place_names = _filter_placeholder_places(raw_place_names)
+    if dropped_place_names:
+        logger.info(
+            "record_moment: dropped placeholder place_names %r — not real places",
+            dropped_place_names,
+        )
     place_ids.extend(
         await _resolve_entity_ids_by_name(
             user_id=user_id,
-            names=arguments.get("place_names") or [],
+            names=kept_place_names,
             note_type="place",
         )
     )
@@ -199,6 +311,15 @@ async def record_moment_tool(*, user_id, arguments, conv_id=None, **_ctx):
     task_ids = list(dict.fromkeys(task_ids))
     note_ids = list(dict.fromkeys(note_ids))
 
+    # Drop task links that don't share a keyword with the moment content.
+    # Belt-and-suspenders to the prompt-layer rule "only link tasks the user
+    # explicitly references" — if the model attaches a task anyway (because
+    # it's in the prep context), the keyword check refuses to persist a link
+    # the moment can't justify.
+    task_ids = await _filter_task_ids_by_keyword_overlap(
+        user_id=user_id, content=content, task_ids=task_ids,
+    )
+
     moment = await create_moment(
         user_id=user_id,
         content=content,

src/fabledassistant/services/tools/notes.py

@@ -235,7 +235,13 @@ async def update_note_tool(*, user_id, arguments, **_ctx):
 
 @tool(
     name="search_notes",
-    description="Find notes or tasks by meaning. Returns a ranked list of matches with short previews. Use this when looking for items on a topic but you don't know the exact title. For the full body of a known item, use read_note instead.",
+    description=(
+        "Find notes or tasks by meaning. Returns a ranked list of matches with "
+        "short previews. Use this when looking for items on a topic but you "
+        "don't know the exact title. For the full body of a known item, use "
+        "read_note instead. Do not include 'task', 'note', or 'project' in the "
+        "`query` — use the `type` and `project` parameters instead."
+    ),
     parameters={
         "query": {"type": "string", "description": "A natural-language description of what you're looking for — concepts, themes, topics, or keywords"},
         "type": {"type": "string", "enum": ["note", "task"], "description": "Restrict results to only notes or only tasks. Omit to search both."},

src/fabledassistant/services/tools/projects.py

@@ -135,20 +135,12 @@ async def update_project_tool(*, user_id, arguments, **_ctx):
     briefing=True,
 )
 async def search_projects_tool(*, user_id, arguments, **_ctx):
-    from difflib import SequenceMatcher
-
     from fabledassistant.services.projects import list_projects
+    from fabledassistant.services.tools._helpers import score_project_match
 
-    query = str(arguments.get("query", "")).lower()
+    query = str(arguments.get("query", ""))
     projects = await list_projects(user_id)
-    scored: list[tuple[float, object]] = []
-    for p in projects:
-        combined = f"{p.title} {p.description or ''} {p.auto_summary or ''}".lower()
-        base_score = SequenceMatcher(None, query, combined).ratio()
-        query_words = set(query.split())
-        overlap = sum(1 for w in query_words if w in combined)
-        score = base_score + overlap * 0.05
-        scored.append((score, p))
+    scored: list[tuple[float, object]] = [(score_project_match(query, p), p) for p in projects]
     scored.sort(key=lambda x: x[0], reverse=True)
     results = []
     for score, p in scored[:5]:
@@ -158,7 +150,7 @@ async def search_projects_tool(*, user_id, arguments, **_ctx):
             "summary_snippet": (p.auto_summary or p.description or "")[:200],
             "score": round(score, 3),
         })
-    return {"type": "projects_list", "data": {"projects": results}}
+    return {"success": True, "type": "projects_list", "data": {"projects": results}}
 
 
 @tool(

src/fabledassistant/services/weather.py

@@ -232,12 +232,23 @@ def parse_weather_card_data(
     }
 
 
-async def get_cached_weather_rows(user_id: int) -> list:
-    """Return raw WeatherCache ORM rows for a user (for card parsing)."""
+async def get_cached_weather_rows(
+    user_id: int,
+    valid_keys: set[str] | None = None,
+) -> list:
+    """Return raw WeatherCache ORM rows for a user (for card parsing).
+
+    If ``valid_keys`` is provided, only rows whose ``location_key`` is in the
+    set are returned. This is how callers drop orphaned cache rows whose
+    location is no longer in the user's ``journal_config.locations`` (e.g.
+    leftovers from the briefing era, or a location that's been removed).
+    Passing an empty set returns no rows.
+    """
     async with async_session() as session:
-        result = await session.execute(
-            select(WeatherCache).where(WeatherCache.user_id == user_id)
-        )
+        stmt = select(WeatherCache).where(WeatherCache.user_id == user_id)
+        if valid_keys is not None:
+            stmt = stmt.where(WeatherCache.location_key.in_(list(valid_keys)))
+        result = await session.execute(stmt)
         return list(result.scalars().all())
 
 

tests/test_calendar_tool_tz.py

@@ -132,3 +132,664 @@ async def test_list_events_bare_date_range_covers_local_day():
     assert (df.year, df.month, df.day, df.hour) == (2026, 9, 30, 4)
     # 2026-09-30 23:59:59 NY (EDT) = 03:59:59 UTC next day
     assert (dt.year, dt.month, dt.day, dt.hour) == (2026, 10, 1, 3)
+
+
+# ── Split date/time field tests (durable shape) ──────────────────────────────
+#
+# These exercise the start_date + start_time path that the model is now
+# steered toward. The split-field shape is structurally immune to the
+# class of bugs where a model emits a TZ-tagged combined datetime that
+# the parser correctly honors but lands on the wrong calendar day for
+# negative-offset users.
+
+
+@pytest.mark.asyncio
+async def test_create_event_split_fields_friday_8am_no_drift_eastern():
+    """The reported bug: 'next Friday at 8am' for a NY user must land on
+    2026-05-01 08:00 NY, never 04-30 19:00. With split fields the model
+    can't TZ-tag the date string, so the calendar day is fixed."""
+    from fabledassistant.services.tools.calendar import create_event_tool
+
+    captured = {}
+
+    async def fake_create_event(**kwargs):
+        captured.update(kwargs)
+        event = AsyncMock()
+        event.to_dict.return_value = {"id": 1}
+        return event
+
+    with patch(
+        "fabledassistant.services.tools.calendar.get_user_tz",
+        AsyncMock(return_value=__import__("zoneinfo").ZoneInfo("America/New_York")),
+    ), patch(
+        "fabledassistant.services.tools.calendar.events_create_event",
+        side_effect=fake_create_event,
+    ):
+        result = await create_event_tool(
+            user_id=1,
+            arguments={
+                "title": "Meeting",
+                "start_date": "2026-05-01",
+                "start_time": "08:00",
+            },
+        )
+
+    assert result["success"] is True
+    utc = captured["start_dt"].astimezone(timezone.utc)
+    # 08:00 NY (EDT, UTC-4) on 2026-05-01 = 12:00 UTC same day
+    assert (utc.year, utc.month, utc.day, utc.hour, utc.minute) == (2026, 5, 1, 12, 0)
+    assert captured["all_day"] is False
+
+
+@pytest.mark.asyncio
+async def test_create_event_split_fields_no_drift_pacific():
+    """Same scenario for a UTC-8 user — the calendar day must be 5/1
+    regardless of how big the offset gets."""
+    from fabledassistant.services.tools.calendar import create_event_tool
+
+    captured = {}
+
+    async def fake_create_event(**kwargs):
+        captured.update(kwargs)
+        event = AsyncMock()
+        event.to_dict.return_value = {"id": 1}
+        return event
+
+    with patch(
+        "fabledassistant.services.tools.calendar.get_user_tz",
+        AsyncMock(return_value=__import__("zoneinfo").ZoneInfo("America/Los_Angeles")),
+    ), patch(
+        "fabledassistant.services.tools.calendar.events_create_event",
+        side_effect=fake_create_event,
+    ):
+        await create_event_tool(
+            user_id=1,
+            arguments={
+                "title": "Standup",
+                "start_date": "2026-05-01",
+                "start_time": "08:00",
+            },
+        )
+
+    utc = captured["start_dt"].astimezone(timezone.utc)
+    # 08:00 LA (PDT, UTC-7) = 15:00 UTC same day
+    assert (utc.year, utc.month, utc.day, utc.hour) == (2026, 5, 1, 15)
+
+
+@pytest.mark.asyncio
+async def test_create_event_split_fields_no_drift_positive_offset():
+    """A positive-offset user (Tokyo, UTC+9) — 08:00 Tokyo on 2026-05-01
+    is 23:00 UTC on 2026-04-30, but the local calendar day must still be
+    stored as 2026-05-01 from the user's perspective."""
+    from fabledassistant.services.tools.calendar import create_event_tool
+
+    captured = {}
+
+    async def fake_create_event(**kwargs):
+        captured.update(kwargs)
+        event = AsyncMock()
+        event.to_dict.return_value = {"id": 1}
+        return event
+
+    with patch(
+        "fabledassistant.services.tools.calendar.get_user_tz",
+        AsyncMock(return_value=__import__("zoneinfo").ZoneInfo("Asia/Tokyo")),
+    ), patch(
+        "fabledassistant.services.tools.calendar.events_create_event",
+        side_effect=fake_create_event,
+    ):
+        await create_event_tool(
+            user_id=1,
+            arguments={
+                "title": "Sync",
+                "start_date": "2026-05-01",
+                "start_time": "08:00",
+            },
+        )
+
+    utc = captured["start_dt"].astimezone(timezone.utc)
+    # 08:00 Tokyo (UTC+9) = 23:00 UTC previous day; the round-trip back
+    # to Tokyo TZ recovers 2026-05-01 08:00.
+    assert (utc.year, utc.month, utc.day, utc.hour) == (2026, 4, 30, 23)
+    tokyo = captured["start_dt"].astimezone(__import__("zoneinfo").ZoneInfo("Asia/Tokyo"))
+    assert (tokyo.year, tokyo.month, tokyo.day, tokyo.hour) == (2026, 5, 1, 8)
+
+
+@pytest.mark.asyncio
+async def test_create_event_split_date_only_is_all_day():
+    """Omitting start_time means the event is all-day; cache row uses
+    local midnight."""
+    from fabledassistant.services.tools.calendar import create_event_tool
+
+    captured = {}
+
+    async def fake_create_event(**kwargs):
+        captured.update(kwargs)
+        event = AsyncMock()
+        event.to_dict.return_value = {"id": 1}
+        return event
+
+    with patch(
+        "fabledassistant.services.tools.calendar.get_user_tz",
+        AsyncMock(return_value=__import__("zoneinfo").ZoneInfo("America/New_York")),
+    ), patch(
+        "fabledassistant.services.tools.calendar.events_create_event",
+        side_effect=fake_create_event,
+    ):
+        await create_event_tool(
+            user_id=1,
+            arguments={"title": "Birthday", "start_date": "2026-09-30"},
+        )
+
+    assert captured["all_day"] is True
+    utc = captured["start_dt"].astimezone(timezone.utc)
+    assert (utc.year, utc.month, utc.day, utc.hour) == (2026, 9, 30, 4)
+
+
+@pytest.mark.asyncio
+async def test_create_event_split_rejects_tz_suffix_in_date():
+    """The whole point of split fields: a TZ suffix on the date string
+    must be rejected, not silently honored."""
+    from fabledassistant.services.tools.calendar import create_event_tool
+
+    with patch(
+        "fabledassistant.services.tools.calendar.get_user_tz",
+        AsyncMock(return_value=__import__("zoneinfo").ZoneInfo("America/New_York")),
+    ):
+        result = await create_event_tool(
+            user_id=1,
+            arguments={"title": "x", "start_date": "2026-05-01Z", "start_time": "08:00"},
+        )
+
+    assert result["success"] is False
+    assert "YYYY-MM-DD" in result["error"]
+
+
+@pytest.mark.asyncio
+async def test_create_event_split_rejects_tz_suffix_in_time():
+    """A TZ suffix on the time string must also be rejected."""
+    from fabledassistant.services.tools.calendar import create_event_tool
+
+    with patch(
+        "fabledassistant.services.tools.calendar.get_user_tz",
+        AsyncMock(return_value=__import__("zoneinfo").ZoneInfo("America/New_York")),
+    ):
+        result = await create_event_tool(
+            user_id=1,
+            arguments={"title": "x", "start_date": "2026-05-01", "start_time": "08:00 UTC"},
+        )
+
+    assert result["success"] is False
+    assert "HH:MM" in result["error"]
+
+
+@pytest.mark.asyncio
+async def test_create_event_legacy_combined_start_still_works():
+    """Backcompat: saved tool-call payloads using the old `start` field
+    must still produce the same UTC datetime as before."""
+    from fabledassistant.services.tools.calendar import create_event_tool
+
+    captured = {}
+
+    async def fake_create_event(**kwargs):
+        captured.update(kwargs)
+        event = AsyncMock()
+        event.to_dict.return_value = {"id": 1}
+        return event
+
+    with patch(
+        "fabledassistant.services.tools.calendar.get_user_tz",
+        AsyncMock(return_value=__import__("zoneinfo").ZoneInfo("America/New_York")),
+    ), patch(
+        "fabledassistant.services.tools.calendar.events_create_event",
+        side_effect=fake_create_event,
+    ):
+        result = await create_event_tool(
+            user_id=1,
+            arguments={"title": "Legacy", "start": "2026-05-01T08:00"},
+        )
+
+    assert result["success"] is True
+    utc = captured["start_dt"].astimezone(timezone.utc)
+    assert (utc.year, utc.month, utc.day, utc.hour) == (2026, 5, 1, 12)
+
+
+@pytest.mark.asyncio
+async def test_update_event_split_fields_reschedule_no_drift():
+    """update_event with split fields must drift no calendar day either."""
+    from fabledassistant.services.tools.calendar import update_event_tool
+
+    captured = {}
+
+    async def fake_find(*, user_id, query):
+        ev = AsyncMock()
+        ev.id = 99
+        ev.title = "Coffee"
+        return [ev]
+
+    async def fake_update(*, user_id, event_id, **fields):
+        captured.update(fields)
+        ev = AsyncMock()
+        ev.to_dict.return_value = {"id": event_id, **fields}
+        return ev
+
+    with patch(
+        "fabledassistant.services.tools.calendar.get_user_tz",
+        AsyncMock(return_value=__import__("zoneinfo").ZoneInfo("America/New_York")),
+    ), patch(
+        "fabledassistant.services.tools.calendar.find_events_by_query",
+        side_effect=fake_find,
+    ), patch(
+        "fabledassistant.services.tools.calendar.events_update_event",
+        side_effect=fake_update,
+    ):
+        result = await update_event_tool(
+            user_id=1,
+            arguments={
+                "query": "Coffee",
+                "start_date": "2026-05-01",
+                "start_time": "08:00",
+            },
+        )
+
+    assert result["success"] is True
+    utc = captured["start_dt"].astimezone(timezone.utc)
+    assert (utc.year, utc.month, utc.day, utc.hour) == (2026, 5, 1, 12)
+
+
+# ── expected_weekday verification (catches "this Friday" → Thursday bugs) ────
+
+
+@pytest.mark.asyncio
+async def test_create_event_expected_weekday_match_succeeds():
+    """When expected_weekday agrees with the resolved local date's
+    weekday, the event is created normally."""
+    from fabledassistant.services.tools.calendar import create_event_tool
+
+    captured = {}
+
+    async def fake_create_event(**kwargs):
+        captured.update(kwargs)
+        event = AsyncMock()
+        event.to_dict.return_value = {"id": 1}
+        return event
+
+    with patch(
+        "fabledassistant.services.tools.calendar.get_user_tz",
+        AsyncMock(return_value=__import__("zoneinfo").ZoneInfo("America/New_York")),
+    ), patch(
+        "fabledassistant.services.tools.calendar.events_create_event",
+        side_effect=fake_create_event,
+    ):
+        result = await create_event_tool(
+            user_id=1,
+            arguments={
+                "title": "Meeting",
+                "start_date": "2026-05-01",  # is a Friday
+                "start_time": "08:00",
+                "expected_weekday": "friday",
+            },
+        )
+
+    assert result["success"] is True
+    assert captured["start_dt"] is not None
+
+
+@pytest.mark.asyncio
+async def test_create_event_expected_weekday_mismatch_rejects_and_names_actual():
+    """The reported failure mode: model picks Thursday and calls it
+    Friday. With expected_weekday set, the create is rejected and the
+    error names the actual weekday so the model can self-correct."""
+    from fabledassistant.services.tools.calendar import create_event_tool
+
+    create_called = False
+
+    async def fake_create_event(**kwargs):
+        nonlocal create_called
+        create_called = True
+        event = AsyncMock()
+        event.to_dict.return_value = {"id": 1}
+        return event
+
+    with patch(
+        "fabledassistant.services.tools.calendar.get_user_tz",
+        AsyncMock(return_value=__import__("zoneinfo").ZoneInfo("America/New_York")),
+    ), patch(
+        "fabledassistant.services.tools.calendar.events_create_event",
+        side_effect=fake_create_event,
+    ):
+        result = await create_event_tool(
+            user_id=1,
+            arguments={
+                "title": "Dentist",
+                "start_date": "2026-04-30",  # Thursday
+                "start_time": "08:00",
+                "expected_weekday": "friday",
+            },
+        )
+
+    assert result["success"] is False
+    assert "Thursday" in result["error"]
+    assert "Friday" in result["error"]
+    # Critical: the event must NOT have been created when the check failed.
+    assert create_called is False
+
+
+@pytest.mark.asyncio
+async def test_create_event_expected_weekday_omitted_skips_check():
+    """Backcompat: when expected_weekday isn't passed, no validation
+    runs — the existing create flow is unchanged."""
+    from fabledassistant.services.tools.calendar import create_event_tool
+
+    captured = {}
+
+    async def fake_create_event(**kwargs):
+        captured.update(kwargs)
+        event = AsyncMock()
+        event.to_dict.return_value = {"id": 1}
+        return event
+
+    with patch(
+        "fabledassistant.services.tools.calendar.get_user_tz",
+        AsyncMock(return_value=__import__("zoneinfo").ZoneInfo("America/New_York")),
+    ), patch(
+        "fabledassistant.services.tools.calendar.events_create_event",
+        side_effect=fake_create_event,
+    ):
+        result = await create_event_tool(
+            user_id=1,
+            arguments={
+                "title": "x",
+                "start_date": "2026-04-30",
+                "start_time": "08:00",
+            },
+        )
+
+    assert result["success"] is True
+
+
+@pytest.mark.asyncio
+async def test_create_event_expected_weekday_invalid_value_rejects():
+    """Garbage in expected_weekday produces a clear validation error,
+    not a silent pass."""
+    from fabledassistant.services.tools.calendar import create_event_tool
+
+    with patch(
+        "fabledassistant.services.tools.calendar.get_user_tz",
+        AsyncMock(return_value=__import__("zoneinfo").ZoneInfo("America/New_York")),
+    ):
+        result = await create_event_tool(
+            user_id=1,
+            arguments={
+                "title": "x",
+                "start_date": "2026-05-01",
+                "start_time": "08:00",
+                "expected_weekday": "fri",  # abbreviation not accepted
+            },
+        )
+
+    assert result["success"] is False
+    assert "weekday" in result["error"].lower()
+
+
+@pytest.mark.asyncio
+async def test_update_event_expected_weekday_mismatch_rejects():
+    """update_event must enforce the same weekday check on reschedules."""
+    from fabledassistant.services.tools.calendar import update_event_tool
+
+    update_called = False
+
+    async def fake_find(*, user_id, query):
+        ev = AsyncMock()
+        ev.id = 99
+        ev.title = "Coffee"
+        return [ev]
+
+    async def fake_update(*, user_id, event_id, **fields):
+        nonlocal update_called
+        update_called = True
+        ev = AsyncMock()
+        ev.to_dict.return_value = {"id": event_id}
+        return ev
+
+    with patch(
+        "fabledassistant.services.tools.calendar.get_user_tz",
+        AsyncMock(return_value=__import__("zoneinfo").ZoneInfo("America/New_York")),
+    ), patch(
+        "fabledassistant.services.tools.calendar.find_events_by_query",
+        side_effect=fake_find,
+    ), patch(
+        "fabledassistant.services.tools.calendar.events_update_event",
+        side_effect=fake_update,
+    ):
+        result = await update_event_tool(
+            user_id=1,
+            arguments={
+                "query": "Coffee",
+                "start_date": "2026-04-30",  # Thursday
+                "start_time": "08:00",
+                "expected_weekday": "friday",
+            },
+        )
+
+    assert result["success"] is False
+    assert "Thursday" in result["error"]
+    assert update_called is False
+
+
+# ── Multi-match disambiguation (Fable #161) ──────────────────────────────────
+
+
+@pytest.mark.asyncio
+async def test_update_event_refuses_ambiguous_query_with_candidates():
+    """The reported failure: model called update_event(query='Appointment')
+    when two events matched. Pre-fix: silently mutated matches[0] (the
+    wrong event). Post-fix: returns success=False with a candidates list
+    so the model can pick the right one."""
+    from fabledassistant.services.tools.calendar import update_event_tool
+
+    # Two events both matching "Appointment"
+    ev_a = AsyncMock()
+    ev_a.id = 2
+    ev_a.title = "Appointment"
+    ev_a.start_dt = __import__("datetime").datetime(2026, 4, 30, 12, 0, tzinfo=timezone.utc)
+    ev_a.location = ""
+    ev_b = AsyncMock()
+    ev_b.id = 15
+    ev_b.title = "Appointment"
+    ev_b.start_dt = __import__("datetime").datetime(2026, 5, 1, 12, 0, tzinfo=timezone.utc)
+    ev_b.location = "Dentist"
+
+    update_called = False
+
+    async def fake_find(*, user_id, query):
+        return [ev_a, ev_b]
+
+    async def fake_update(*, user_id, event_id, **fields):
+        nonlocal update_called
+        update_called = True
+        return AsyncMock()
+
+    with patch(
+        "fabledassistant.services.tools.calendar.find_events_by_query",
+        side_effect=fake_find,
+    ), patch(
+        "fabledassistant.services.tools.calendar.events_update_event",
+        side_effect=fake_update,
+    ):
+        result = await update_event_tool(
+            user_id=1,
+            arguments={"query": "Appointment", "title": "Dentist"},
+        )
+
+    assert result["success"] is False
+    assert "Found 2 events" in result["error"]
+    assert "event_id" in result["error"].lower()
+    assert "candidates" in result
+    candidate_ids = [c["id"] for c in result["candidates"]]
+    assert candidate_ids == [2, 15]
+    # Critical: nothing was mutated.
+    assert update_called is False
+
+
+@pytest.mark.asyncio
+async def test_update_event_with_event_id_skips_query_lookup():
+    """Once the model picks a candidate via event_id, the call proceeds
+    against that exact event — no query, no ambiguity."""
+    from fabledassistant.services.tools.calendar import update_event_tool
+
+    # find_events_by_query should NOT be called when event_id is supplied
+    find_called = False
+
+    async def fake_find(*, user_id, query):
+        nonlocal find_called
+        find_called = True
+        return []
+
+    target = AsyncMock()
+    target.id = 15
+    target.title = "Appointment"
+    target.start_dt = __import__("datetime").datetime(2026, 5, 1, 12, 0, tzinfo=timezone.utc)
+    target.location = ""
+
+    async def fake_get_event(*, user_id, event_id):
+        return target if event_id == 15 else None
+
+    captured = {}
+
+    async def fake_update(*, user_id, event_id, **fields):
+        captured["event_id"] = event_id
+        captured.update(fields)
+        ev = AsyncMock()
+        ev.to_dict.return_value = {"id": event_id, **fields}
+        return ev
+
+    with patch(
+        "fabledassistant.services.tools.calendar.find_events_by_query",
+        side_effect=fake_find,
+    ), patch(
+        "fabledassistant.services.events.get_event",
+        side_effect=fake_get_event,
+    ), patch(
+        "fabledassistant.services.tools.calendar.events_update_event",
+        side_effect=fake_update,
+    ):
+        result = await update_event_tool(
+            user_id=1,
+            arguments={"event_id": 15, "title": "Dentist: Permanent Crown Fitting"},
+        )
+
+    assert result["success"] is True
+    assert captured["event_id"] == 15
+    assert captured["title"] == "Dentist: Permanent Crown Fitting"
+    assert find_called is False
+
+
+@pytest.mark.asyncio
+async def test_update_event_with_event_id_not_found_returns_error():
+    """A bad event_id (non-existent) must surface clearly, not silently
+    fall back to query-based lookup."""
+    from fabledassistant.services.tools.calendar import update_event_tool
+
+    async def fake_get_event(*, user_id, event_id):
+        return None
+
+    with patch(
+        "fabledassistant.services.events.get_event",
+        side_effect=fake_get_event,
+    ):
+        result = await update_event_tool(
+            user_id=1,
+            arguments={"event_id": 999, "title": "anything"},
+        )
+
+    assert result["success"] is False
+    assert "999" in result["error"]
+    assert "No event found" in result["error"]
+
+
+@pytest.mark.asyncio
+async def test_update_event_neither_query_nor_event_id_returns_error():
+    """Calling update_event with neither identifier is a usage error."""
+    from fabledassistant.services.tools.calendar import update_event_tool
+
+    result = await update_event_tool(user_id=1, arguments={"title": "x"})
+    assert result["success"] is False
+    assert "query or event_id" in result["error"]
+
+
+@pytest.mark.asyncio
+async def test_delete_event_refuses_ambiguous_query_with_candidates():
+    """delete_event must enforce the same disambiguation. Costly to get
+    wrong — silent matches[0] would delete the wrong event entirely."""
+    from fabledassistant.services.tools.calendar import delete_event_tool
+
+    ev_a = AsyncMock()
+    ev_a.id = 2; ev_a.title = "Appointment"
+    ev_a.start_dt = __import__("datetime").datetime(2026, 4, 30, 12, 0, tzinfo=timezone.utc)
+    ev_a.location = ""
+    ev_b = AsyncMock()
+    ev_b.id = 15; ev_b.title = "Appointment"
+    ev_b.start_dt = __import__("datetime").datetime(2026, 5, 1, 12, 0, tzinfo=timezone.utc)
+    ev_b.location = "Dentist"
+
+    delete_called = False
+
+    async def fake_find(*, user_id, query):
+        return [ev_a, ev_b]
+
+    async def fake_delete(*, user_id, event_id):
+        nonlocal delete_called
+        delete_called = True
+
+    with patch(
+        "fabledassistant.services.tools.calendar.find_events_by_query",
+        side_effect=fake_find,
+    ), patch(
+        "fabledassistant.services.tools.calendar.events_delete_event",
+        side_effect=fake_delete,
+    ):
+        result = await delete_event_tool(
+            user_id=1, arguments={"query": "Appointment"},
+        )
+
+    assert result["success"] is False
+    assert len(result["candidates"]) == 2
+    # Most important assertion: nothing was actually deleted.
+    assert delete_called is False
+
+
+@pytest.mark.asyncio
+async def test_create_event_weekday_check_uses_local_not_utc():
+    """The weekday check must use the LOCAL date, not the UTC date.
+    A late-evening Friday event in Tokyo (UTC+9) crosses midnight UTC,
+    so a UTC-day check would call it Saturday — but the user's calendar
+    says Friday. The check must respect the user's local view."""
+    from fabledassistant.services.tools.calendar import create_event_tool
+
+    captured = {}
+
+    async def fake_create_event(**kwargs):
+        captured.update(kwargs)
+        event = AsyncMock()
+        event.to_dict.return_value = {"id": 1}
+        return event
+
+    with patch(
+        "fabledassistant.services.tools.calendar.get_user_tz",
+        AsyncMock(return_value=__import__("zoneinfo").ZoneInfo("Asia/Tokyo")),
+    ), patch(
+        "fabledassistant.services.tools.calendar.events_create_event",
+        side_effect=fake_create_event,
+    ):
+        result = await create_event_tool(
+            user_id=1,
+            arguments={
+                "title": "Friday night",
+                "start_date": "2026-05-01",  # Friday in Tokyo
+                "start_time": "23:00",       # 14:00 UTC same day; safe
+                "expected_weekday": "friday",
+            },
+        )
+
+    assert result["success"] is True

tests/test_events_service.py

@@ -14,7 +14,7 @@ def _make_mock_session():
 
 
 def _make_mock_event(id=1, user_id=1, uid="uid-abc", title="Meeting",
-                     caldav_uid="", color=""):
+                     caldav_uid="", color="", duration_minutes=60):
     e = MagicMock()
     e.id = id
     e.user_id = user_id
@@ -23,7 +23,14 @@ def _make_mock_event(id=1, user_id=1, uid="uid-abc", title="Meeting",
     e.caldav_uid = caldav_uid
     e.color = color
     e.start_dt = datetime(2026, 3, 25, 10, 0, tzinfo=timezone.utc)
-    e.end_dt = datetime(2026, 3, 25, 11, 0, tzinfo=timezone.utc)
+    e.duration_minutes = duration_minutes
+    # end_dt is derived; mirror the property's behavior on the mock so
+    # service code that reads `event.end_dt` gets a sensible value.
+    if duration_minutes is None:
+        e.end_dt = None
+    else:
+        from datetime import timedelta
+        e.end_dt = e.start_dt + timedelta(minutes=duration_minutes)
     e.all_day = False
     e.description = ""
     e.location = ""
@@ -32,8 +39,9 @@ def _make_mock_event(id=1, user_id=1, uid="uid-abc", title="Meeting",
     e.to_dict.return_value = {
         "id": id, "uid": uid, "title": title,
         "caldav_uid": caldav_uid, "color": color,
-        "start_dt": datetime(2026, 3, 25, 10, 0, tzinfo=timezone.utc).isoformat(),
-        "end_dt": datetime(2026, 3, 25, 11, 0, tzinfo=timezone.utc).isoformat(),
+        "start_dt": e.start_dt.isoformat(),
+        "end_dt": e.end_dt.isoformat() if e.end_dt else None,
+        "duration_minutes": duration_minutes,
     }
     return e
 
@@ -124,6 +132,195 @@ async def test_update_event_fires_caldav_push():
         assert mock_task.called
 
 
+# ── Duration-model write-side guarantees (Fable #160) ─────────────────────────
+
+
+def test_normalize_duration_from_end_dt():
+    """end_dt sugar converts to a positive minute count anchored on start."""
+    from fabledassistant.services.events import _normalize_duration
+    start = datetime(2026, 5, 1, 8, 0, tzinfo=timezone.utc)
+    end = datetime(2026, 5, 1, 9, 30, tzinfo=timezone.utc)
+    assert _normalize_duration(start_dt=start, end_dt=end, duration_minutes=None) == 90
+
+
+def test_normalize_duration_zero_is_valid_point_event():
+    """end_dt == start_dt → duration 0. The point-with-zero-duration case
+    is rare but legal (e.g. an instant marker); the duration model treats
+    it the same as duration None for display purposes."""
+    from fabledassistant.services.events import _normalize_duration
+    same = datetime(2026, 5, 1, 8, 0, tzinfo=timezone.utc)
+    assert _normalize_duration(start_dt=same, end_dt=same, duration_minutes=None) == 0
+
+
+def test_normalize_duration_rejects_end_before_start():
+    """The exact 2026-04-29 prod failure: end 32 days before start.
+    The duration model makes this inexpressible at the schema level
+    via a CHECK constraint, but write-path callers still get a
+    helpful ValueError if they construct an inconsistent (start, end)
+    pair via the end_dt sugar."""
+    from fabledassistant.services.events import _normalize_duration
+    start = datetime(2026, 5, 1, 12, 0, tzinfo=timezone.utc)
+    end_before = datetime(2026, 3, 30, 12, 0, tzinfo=timezone.utc)
+    with pytest.raises(ValueError, match="at or after start_dt"):
+        _normalize_duration(
+            start_dt=start, end_dt=end_before, duration_minutes=None,
+        )
+
+
+def test_normalize_duration_rejects_negative_duration():
+    """Direct duration_minutes < 0 is rejected. Mirrors the DB CHECK
+    constraint at the service boundary so callers get a clean error
+    rather than a constraint violation from psycopg."""
+    from fabledassistant.services.events import _normalize_duration
+    start = datetime(2026, 5, 1, 12, 0, tzinfo=timezone.utc)
+    with pytest.raises(ValueError, match="must be >= 0"):
+        _normalize_duration(start_dt=start, end_dt=None, duration_minutes=-15)
+
+
+def test_normalize_duration_rejects_inconsistent_end_and_duration():
+    """If a caller passes both end_dt AND duration_minutes that disagree,
+    the inconsistency is surfaced rather than silently picking one."""
+    from fabledassistant.services.events import _normalize_duration
+    start = datetime(2026, 5, 1, 12, 0, tzinfo=timezone.utc)
+    end = datetime(2026, 5, 1, 13, 0, tzinfo=timezone.utc)  # implies 60 min
+    with pytest.raises(ValueError, match="implies 60 minutes"):
+        _normalize_duration(
+            start_dt=start, end_dt=end, duration_minutes=30,
+        )
+
+
+def test_normalize_duration_none_for_open_ended():
+    """Both inputs None → None duration (open-ended event)."""
+    from fabledassistant.services.events import _normalize_duration
+    start = datetime(2026, 5, 1, 12, 0, tzinfo=timezone.utc)
+    assert _normalize_duration(
+        start_dt=start, end_dt=None, duration_minutes=None,
+    ) is None
+
+
+@pytest.mark.asyncio
+async def test_create_event_rejects_end_before_start():
+    """Service-level rejection — same scenario as the prod bug, surfaced
+    cleanly for tool / route callers via ValueError."""
+    from fabledassistant.services.events import create_event
+    start = datetime(2026, 5, 1, 12, 0, tzinfo=timezone.utc)
+    end_before = datetime(2026, 3, 30, 12, 0, tzinfo=timezone.utc)
+    with pytest.raises(ValueError, match="at or after start_dt"):
+        await create_event(
+            user_id=1, title="Bad",
+            start_dt=start, end_dt=end_before,
+        )
+
+
+@pytest.mark.asyncio
+async def test_update_event_preserves_duration_when_only_start_changes():
+    """Sliding semantics: when the user moves an event by changing only
+    start_dt, the existing duration_minutes is preserved as-is. The new
+    effective end_dt slides forward with the start. This is a behavioral
+    upgrade vs. the old end_dt model, where moving start past the
+    stored end made the event 'go backward in time'."""
+    mock_event = _make_mock_event(duration_minutes=60)  # start 10:00, end 11:00
+    mock_session = _make_mock_session()
+    mock_result = MagicMock()
+    mock_result.scalar_one_or_none.return_value = mock_event
+    mock_session.execute = AsyncMock(return_value=mock_result)
+
+    with patch("fabledassistant.services.events.async_session") as mock_cls, \
+         patch("fabledassistant.services.events.asyncio.create_task"):
+        mock_cls.return_value = mock_session
+        from fabledassistant.services.events import update_event
+        # Move start to 12:00; effective end becomes 13:00 automatically.
+        result = await update_event(
+            user_id=1, event_id=1,
+            start_dt=datetime(2026, 3, 25, 12, 0, tzinfo=timezone.utc),
+        )
+    assert result is not None
+    # duration_minutes was NOT touched; mock_event still has 60.
+    assert mock_event.duration_minutes == 60
+
+
+@pytest.mark.asyncio
+async def test_update_event_clearing_end_dt_clears_duration():
+    """Passing end_dt=None on update is the documented way to clear the
+    end (turn a timed event into a point event). The service must
+    translate that into duration_minutes=None, not leave the prior
+    value in place."""
+    mock_event = _make_mock_event(duration_minutes=60)
+    mock_session = _make_mock_session()
+    mock_result = MagicMock()
+    mock_result.scalar_one_or_none.return_value = mock_event
+    mock_session.execute = AsyncMock(return_value=mock_result)
+
+    with patch("fabledassistant.services.events.async_session") as mock_cls, \
+         patch("fabledassistant.services.events.asyncio.create_task"):
+        mock_cls.return_value = mock_session
+        from fabledassistant.services.events import update_event
+        await update_event(user_id=1, event_id=1, end_dt=None)
+    assert mock_event.duration_minutes is None
+
+
+@pytest.mark.asyncio
+async def test_list_events_includes_point_event_in_window():
+    """A point event (duration_minutes=None) surfaces when its start
+    is in the window. Replaces the prior 'corrupt end_dt' regression
+    test — the duration model can't represent that state, but the
+    same code path is exercised here for point events."""
+    mock_event = _make_mock_event(duration_minutes=None)
+    # Point event in the upcoming window
+    mock_event.start_dt = datetime(2026, 5, 1, 12, 0, tzinfo=timezone.utc)
+    mock_event.end_dt = None
+    mock_event.to_dict.return_value = {
+        "id": 1, "title": "Point",
+        "start_dt": mock_event.start_dt.isoformat(),
+        "end_dt": None,
+        "duration_minutes": None,
+    }
+    mock_session = _make_mock_session()
+    mock_result = MagicMock()
+    mock_result.scalars.return_value.all.return_value = [mock_event]
+    mock_session.execute = AsyncMock(return_value=mock_result)
+
+    with patch("fabledassistant.services.events.async_session") as mock_cls:
+        mock_cls.return_value = mock_session
+        from fabledassistant.services.events import list_events
+        results = await list_events(
+            user_id=1,
+            date_from=datetime(2026, 4, 29, tzinfo=timezone.utc),
+            date_to=datetime(2026, 5, 27, tzinfo=timezone.utc),
+        )
+        assert len(results) == 1
+        assert results[0]["id"] == 1
+
+
+@pytest.mark.asyncio
+async def test_list_events_excludes_timed_event_that_already_ended():
+    """A timed event whose start + duration is before the window must
+    NOT surface. Verifies the Python-side refinement actually works
+    against the coarse SQL prefilter."""
+    mock_event = _make_mock_event(duration_minutes=60)
+    # Start 4/20 12:00, end 4/20 13:00; window is 4/29 → 5/27 — fully past.
+    mock_event.start_dt = datetime(2026, 4, 20, 12, 0, tzinfo=timezone.utc)
+    mock_event.end_dt = datetime(2026, 4, 20, 13, 0, tzinfo=timezone.utc)
+    mock_event.to_dict.return_value = {
+        "id": 1, "start_dt": mock_event.start_dt.isoformat(),
+        "end_dt": mock_event.end_dt.isoformat(), "duration_minutes": 60,
+    }
+    mock_session = _make_mock_session()
+    mock_result = MagicMock()
+    mock_result.scalars.return_value.all.return_value = [mock_event]
+    mock_session.execute = AsyncMock(return_value=mock_result)
+
+    with patch("fabledassistant.services.events.async_session") as mock_cls:
+        mock_cls.return_value = mock_session
+        from fabledassistant.services.events import list_events
+        results = await list_events(
+            user_id=1,
+            date_from=datetime(2026, 4, 29, tzinfo=timezone.utc),
+            date_to=datetime(2026, 5, 27, tzinfo=timezone.utc),
+        )
+        assert results == []
+
+
 @pytest.mark.asyncio
 async def test_tools_calendar_always_available():
     """Calendar tools must appear in get_tools_for_user even without CalDAV."""

tests/test_journal_closeout.py

@@ -0,0 +1,249 @@
+"""Tests for journal closeout extraction helpers."""
+
+import datetime
+from types import SimpleNamespace
+from unittest.mock import AsyncMock, MagicMock, patch
+
+import pytest
+
+
+def _msg(role: str, content: str, kind: str | None = None):
+    """Build a Message-like stand-in for the filter helpers."""
+    metadata = {"kind": kind} if kind else None
+    return SimpleNamespace(role=role, content=content, msg_metadata=metadata)
+
+
+def _fake_conv(conv_id: int = 1):
+    return SimpleNamespace(id=conv_id)
+
+
+def _patch_db(messages, conv=None):
+    """Build a context manager that fakes async_session() and the two
+    select() calls (conversation lookup + messages query)."""
+    session = AsyncMock()
+    session.execute = AsyncMock()
+    conv_result = MagicMock()
+    conv_result.scalar_one_or_none = MagicMock(return_value=conv)
+    msg_result = MagicMock()
+    scalars = MagicMock()
+    scalars.all = MagicMock(return_value=list(messages))
+    msg_result.scalars = MagicMock(return_value=scalars)
+    session.execute.side_effect = [conv_result, msg_result]
+
+    session_ctx = MagicMock()
+    session_ctx.__aenter__ = AsyncMock(return_value=session)
+    session_ctx.__aexit__ = AsyncMock(return_value=None)
+    return session_ctx
+
+
+def test_filter_excludes_daily_prep_messages():
+    from fabledassistant.services.journal_closeout import _filter_messages
+
+    msgs = [
+        _msg("assistant", "Good morning — here is today's plan…", kind="daily_prep"),
+        _msg("user", "I want to focus on the auth refactor today."),
+        _msg("assistant", "Got it. I'll keep tool calls quiet."),
+    ]
+    kept = _filter_messages(msgs)
+    contents = [m.content for m in kept]
+    assert "Good morning — here is today's plan…" not in contents
+    assert "I want to focus on the auth refactor today." in contents
+    assert "Got it. I'll keep tool calls quiet." in contents
+
+
+def test_build_transcript_labels_roles_and_caps_content():
+    from fabledassistant.services.journal_closeout import _build_transcript
+
+    msgs = [
+        _msg("user", "hello"),
+        _msg("assistant", "hi"),
+        _msg("user", "x" * 600),
+    ]
+    out = _build_transcript(msgs)
+    lines = out.splitlines()
+    assert lines[0] == "USER: hello"
+    assert lines[1] == "ASSISTANT: hi"
+    # Third line content truncated to 500 chars
+    assert lines[2].startswith("USER: ")
+    assert len(lines[2]) == len("USER: ") + 500
+
+
+def test_build_transcript_keeps_only_last_20_messages():
+    from fabledassistant.services.journal_closeout import _build_transcript
+
+    msgs = [_msg("user", f"msg-{i}") for i in range(30)]
+    out = _build_transcript(msgs)
+    lines = out.splitlines()
+    assert len(lines) == 20
+    # Newest 20 means msg-10 through msg-29
+    assert lines[0] == "USER: msg-10"
+    assert lines[-1] == "USER: msg-29"
+
+
+def test_system_prompt_lists_structured_fields_to_exclude():
+    """The prompt must explicitly tell the LLM not to restate structured
+    fields, so the freeform learned_summary stays a narrow lane."""
+    from fabledassistant.services.journal_closeout import SYSTEM_PROMPT
+
+    text = SYSTEM_PROMPT.lower()
+    for field in ("name", "job title", "industry", "expertise", "response style", "tone", "interests"):
+        assert field in text, f"system prompt should mention '{field}'"
+    assert "(nothing to note)" in SYSTEM_PROMPT
+
+
+@pytest.mark.asyncio
+async def test_run_for_user_happy_path_appends_bullets():
+    from fabledassistant.services import journal_closeout
+
+    yesterday = datetime.date(2026, 5, 11)
+    msgs = [
+        _msg("assistant", "Good morning — here's today.", kind="daily_prep"),
+        _msg("user", "Skip the news section — I never read it."),
+        _msg("assistant", "Noted. Will drop it."),
+    ]
+
+    with (
+        patch.object(journal_closeout, "async_session", return_value=_patch_db(msgs, conv=_fake_conv())),
+        patch.object(journal_closeout, "get_setting", new=AsyncMock(return_value="bg-model")),
+        patch.object(journal_closeout, "generate_completion", new=AsyncMock(return_value="- User skips news section")),
+        patch.object(journal_closeout, "append_observations", new=AsyncMock()) as mock_append,
+    ):
+        await journal_closeout.run_for_user(user_id=42, yesterday=yesterday)
+
+    mock_append.assert_awaited_once_with(42, "- User skips news section")
+
+
+@pytest.mark.asyncio
+async def test_run_for_user_skips_when_no_conversation():
+    from fabledassistant.services import journal_closeout
+
+    with (
+        patch.object(journal_closeout, "async_session", return_value=_patch_db([], conv=None)),
+        patch.object(journal_closeout, "append_observations", new=AsyncMock()) as mock_append,
+        patch.object(journal_closeout, "generate_completion", new=AsyncMock()) as mock_llm,
+    ):
+        await journal_closeout.run_for_user(user_id=42, yesterday=datetime.date(2026, 5, 11))
+
+    mock_append.assert_not_awaited()
+    mock_llm.assert_not_awaited()
+
+
+@pytest.mark.asyncio
+async def test_run_for_user_skips_when_only_prep_message_after_filter():
+    """If only the daily_prep message exists, the in-Python filter pass
+    leaves zero messages and we short-circuit before the LLM."""
+    from fabledassistant.services import journal_closeout
+
+    msgs_post_sql = [
+        _msg("assistant", "Daily prep block.", kind="daily_prep"),
+    ]
+    with (
+        patch.object(journal_closeout, "async_session", return_value=_patch_db(msgs_post_sql, conv=_fake_conv())),
+        patch.object(journal_closeout, "append_observations", new=AsyncMock()) as mock_append,
+        patch.object(journal_closeout, "generate_completion", new=AsyncMock()) as mock_llm,
+    ):
+        await journal_closeout.run_for_user(user_id=42, yesterday=datetime.date(2026, 5, 11))
+
+    mock_append.assert_not_awaited()
+    mock_llm.assert_not_awaited()
+
+
+@pytest.mark.asyncio
+async def test_run_for_user_respects_nothing_to_note_sentinel():
+    from fabledassistant.services import journal_closeout
+
+    msgs = [_msg("user", "hi"), _msg("assistant", "hi back")]
+    with (
+        patch.object(journal_closeout, "async_session", return_value=_patch_db(msgs, conv=_fake_conv())),
+        patch.object(journal_closeout, "get_setting", new=AsyncMock(return_value="bg-model")),
+        patch.object(journal_closeout, "generate_completion", new=AsyncMock(return_value="(nothing to note)")),
+        patch.object(journal_closeout, "append_observations", new=AsyncMock()) as mock_append,
+    ):
+        await journal_closeout.run_for_user(user_id=42, yesterday=datetime.date(2026, 5, 11))
+
+    mock_append.assert_not_awaited()
+
+
+@pytest.mark.asyncio
+async def test_update_user_schedule_registers_closeout_when_enabled(monkeypatch):
+    from fabledassistant.services import journal_scheduler as sched
+
+    fake_scheduler = MagicMock()
+    fake_scheduler.get_job = MagicMock(return_value=None)
+    monkeypatch.setattr(sched, "_scheduler", fake_scheduler)
+    monkeypatch.setattr(sched, "get_journal_config", AsyncMock(return_value={
+        "prep_enabled": False,           # isolate the closeout job
+        "closeout_enabled": True,
+        "day_rollover_hour": 4,
+    }))
+    monkeypatch.setattr(sched, "get_user_timezone", AsyncMock(return_value="UTC"))
+
+    await sched.update_user_schedule(user_id=7)
+
+    added = [c.kwargs.get("id") for c in fake_scheduler.add_job.call_args_list]
+    assert "journal_closeout_7" in added
+
+
+@pytest.mark.asyncio
+async def test_update_user_schedule_does_not_register_closeout_when_disabled(monkeypatch):
+    from fabledassistant.services import journal_scheduler as sched
+
+    fake_scheduler = MagicMock()
+    fake_scheduler.get_job = MagicMock(return_value=None)
+    monkeypatch.setattr(sched, "_scheduler", fake_scheduler)
+    monkeypatch.setattr(sched, "get_journal_config", AsyncMock(return_value={
+        "prep_enabled": False,
+        "closeout_enabled": False,
+        "day_rollover_hour": 4,
+    }))
+    monkeypatch.setattr(sched, "get_user_timezone", AsyncMock(return_value="UTC"))
+
+    await sched.update_user_schedule(user_id=7)
+
+    added = [c.kwargs.get("id") for c in fake_scheduler.add_job.call_args_list]
+    assert "journal_closeout_7" not in added
+
+
+@pytest.mark.asyncio
+async def test_closeout_catchup_skips_when_already_have_entry(monkeypatch):
+    from fabledassistant.services import journal_scheduler as sched
+
+    monkeypatch.setattr(sched, "get_user_timezone", AsyncMock(return_value="UTC"))
+    monkeypatch.setattr(sched, "get_journal_config", AsyncMock(return_value={
+        "closeout_enabled": True,
+        "day_rollover_hour": 0,  # slot has always passed
+    }))
+    yesterday = (datetime.datetime.now(datetime.timezone.utc) - datetime.timedelta(days=1)).date()
+    fake_profile = SimpleNamespace(observations_raw=[{"date": yesterday.isoformat(), "bullets": "..."}])
+
+    from fabledassistant.services import user_profile as up
+    monkeypatch.setattr(up, "get_profile", AsyncMock(return_value=fake_profile))
+
+    run_mock = AsyncMock()
+    from fabledassistant.services import journal_closeout as jc
+    monkeypatch.setattr(jc, "run_for_user", run_mock)
+
+    await sched._closeout_catchup(user_id=7)
+    run_mock.assert_not_awaited()
+
+
+@pytest.mark.asyncio
+async def test_closeout_catchup_runs_when_no_entry_yet(monkeypatch):
+    from fabledassistant.services import journal_scheduler as sched
+
+    monkeypatch.setattr(sched, "get_user_timezone", AsyncMock(return_value="UTC"))
+    monkeypatch.setattr(sched, "get_journal_config", AsyncMock(return_value={
+        "closeout_enabled": True,
+        "day_rollover_hour": 0,
+    }))
+    fake_profile = SimpleNamespace(observations_raw=[])
+
+    from fabledassistant.services import user_profile as up
+    monkeypatch.setattr(up, "get_profile", AsyncMock(return_value=fake_profile))
+
+    run_mock = AsyncMock()
+    from fabledassistant.services import journal_closeout as jc
+    monkeypatch.setattr(jc, "run_for_user", run_mock)
+
+    await sched._closeout_catchup(user_id=7)
+    run_mock.assert_awaited_once()

tests/test_journal_prep_filtering.py

@@ -0,0 +1,193 @@
+"""Tests for the journal prep filtering helpers added in #159."""
+
+import datetime
+from types import SimpleNamespace
+from zoneinfo import ZoneInfo
+
+import pytest
+
+
+# ── _task_to_prep_dict ────────────────────────────────────────────────────────
+
+
+def test_task_to_prep_dict_marks_overdue_with_days_count():
+    from fabledassistant.services.journal_prep import _task_to_prep_dict
+
+    today = datetime.date(2026, 4, 29)
+    task = SimpleNamespace(
+        id=2, title="Research Weston's ADHD Evaluation",
+        status="todo", priority="high",
+        due_date=datetime.date(2026, 2, 20),
+    )
+    d = _task_to_prep_dict(task, today)
+    assert d["days_overdue"] == 68
+    assert d["due_date"] == "2026-02-20"
+
+
+def test_task_to_prep_dict_due_today_no_overdue_marker():
+    from fabledassistant.services.journal_prep import _task_to_prep_dict
+
+    today = datetime.date(2026, 4, 29)
+    task = SimpleNamespace(
+        id=10, title="Pick up dry cleaning",
+        status="todo", priority="none",
+        due_date=today,
+    )
+    d = _task_to_prep_dict(task, today)
+    assert "days_overdue" not in d
+
+
+def test_task_to_prep_dict_handles_no_due_date():
+    from fabledassistant.services.journal_prep import _task_to_prep_dict
+
+    task = SimpleNamespace(
+        id=11, title="Long-running side project",
+        status="in_progress", priority="medium",
+        due_date=None,
+    )
+    d = _task_to_prep_dict(task, datetime.date(2026, 4, 29))
+    assert d["due_date"] is None
+    assert "days_overdue" not in d
+
+
+# ── _filter_proximate_events ──────────────────────────────────────────────────
+
+
+def test_filter_proximate_drops_far_future_recurring_event():
+    """The reported failure: a recurring Birthday event with start_dt
+    2026-09-29 surfaced in every daily prep. The proximity filter drops it."""
+    from fabledassistant.services.journal_prep import _filter_proximate_events
+
+    events = [
+        {"id": 13, "title": "Birthday", "start_dt": "2026-09-29T00:00:00+00:00"},
+    ]
+    kept = _filter_proximate_events(
+        events,
+        day_date=datetime.date(2026, 4, 29),
+        user_tz=ZoneInfo("America/New_York"),
+    )
+    assert kept == []
+
+
+def test_filter_proximate_keeps_events_within_window():
+    """Events within ±7 days of the prep date stay."""
+    from fabledassistant.services.journal_prep import _filter_proximate_events
+
+    events = [
+        {"id": 1, "title": "Today", "start_dt": "2026-04-29T13:00:00+00:00"},
+        {"id": 2, "title": "Tomorrow", "start_dt": "2026-04-30T12:00:00+00:00"},
+        {"id": 3, "title": "Next week", "start_dt": "2026-05-05T15:00:00+00:00"},
+        {"id": 4, "title": "Two weeks out", "start_dt": "2026-05-15T15:00:00+00:00"},
+    ]
+    kept = _filter_proximate_events(
+        events,
+        day_date=datetime.date(2026, 4, 29),
+        user_tz=ZoneInfo("America/New_York"),
+    )
+    kept_ids = [e["id"] for e in kept]
+    assert 1 in kept_ids
+    assert 2 in kept_ids
+    assert 3 in kept_ids
+    assert 4 not in kept_ids
+
+
+def test_filter_proximate_uses_local_date_not_utc():
+    """An event at 04:30 UTC on 2026-04-30 = 00:30 local on 2026-04-30 in
+    NY (EDT, UTC-4). Local date is 2026-04-30, delta from 2026-04-29 = 1
+    day. Must NOT cross-classify based on UTC date alone."""
+    from fabledassistant.services.journal_prep import _filter_proximate_events
+
+    events = [
+        {"id": 99, "title": "Late-night dentist", "start_dt": "2026-04-30T04:30:00+00:00"},
+    ]
+    kept = _filter_proximate_events(
+        events,
+        day_date=datetime.date(2026, 4, 29),
+        user_tz=ZoneInfo("America/New_York"),
+    )
+    assert len(kept) == 1
+
+
+def test_filter_proximate_keeps_unparseable_dates():
+    """Bad date strings are kept rather than silently suppressing real
+    events on a parser bug."""
+    from fabledassistant.services.journal_prep import _filter_proximate_events
+
+    events = [
+        {"id": 50, "title": "Garbage", "start_dt": "not-a-date"},
+        {"id": 51, "title": "Empty", "start_dt": ""},
+        {"id": 52, "title": "Missing"},
+    ]
+    kept = _filter_proximate_events(
+        events,
+        day_date=datetime.date(2026, 4, 29),
+        user_tz=ZoneInfo("America/New_York"),
+    )
+    assert len(kept) == 3
+
+
+# ── _render_sections_for_prompt — overdue framing ────────────────────────────
+
+
+def test_render_overdue_includes_staleness_duration():
+    """The rendered prompt block must surface days_overdue so the LLM
+    can frame stale tasks correctly."""
+    from fabledassistant.services.journal_prep import _render_sections_for_prompt
+
+    sections = {
+        "tasks_due_today": [],
+        "tasks_upcoming": [],
+        "tasks_overdue": [{
+            "id": 2, "title": "Research Weston's ADHD Evaluation",
+            "status": "todo", "priority": "high",
+            "due_date": "2026-02-20", "days_overdue": 68,
+        }],
+    }
+    rendered = _render_sections_for_prompt(sections)
+    assert "OVERDUE TASKS" in rendered
+    assert "68 days ago" in rendered
+    assert "2026-02-20" in rendered
+    # Crucially, NOT framed as due today.
+    assert "DUE TODAY" not in rendered
+
+
+def test_render_due_today_no_due_date_repetition():
+    """Tasks in the DUE TODAY bucket don't need the (due 2026-04-29)
+    parenthetical — the section header already says 'today'."""
+    from fabledassistant.services.journal_prep import _render_sections_for_prompt
+
+    sections = {
+        "tasks_due_today": [{
+            "id": 1, "title": "Pick up dry cleaning",
+            "status": "todo", "priority": "none",
+            "due_date": "2026-04-29",
+        }],
+        "tasks_upcoming": [],
+        "tasks_overdue": [],
+    }
+    rendered = _render_sections_for_prompt(sections)
+    assert "TASKS DUE TODAY" in rendered
+    assert "Pick up dry cleaning" in rendered
+    # The line itself shouldn't repeat the due date.
+    line = next(
+        (l for l in rendered.splitlines() if "Pick up dry cleaning" in l),
+        "",
+    )
+    assert "2026-04-29" not in line
+
+
+def test_render_three_buckets_in_correct_order():
+    """When all three buckets have content, the prompt sees them in
+    DUE TODAY → UPCOMING → OVERDUE order so the LLM leads with today."""
+    from fabledassistant.services.journal_prep import _render_sections_for_prompt
+
+    sections = {
+        "tasks_due_today": [{"id": 1, "title": "Today task", "status": "todo", "priority": "none", "due_date": "2026-04-29"}],
+        "tasks_upcoming": [{"id": 2, "title": "Upcoming task", "status": "todo", "priority": "none", "due_date": "2026-05-02"}],
+        "tasks_overdue": [{"id": 3, "title": "Stale task", "status": "todo", "priority": "none", "due_date": "2026-02-20", "days_overdue": 68}],
+    }
+    rendered = _render_sections_for_prompt(sections)
+    today_idx = rendered.index("TASKS DUE TODAY")
+    upcoming_idx = rendered.index("UPCOMING TASKS")
+    overdue_idx = rendered.index("OVERDUE TASKS")
+    assert today_idx < upcoming_idx < overdue_idx

tests/test_record_moment_guards.py

@@ -0,0 +1,181 @@
+"""Tests for the record_moment server-side data-hygiene guards.
+
+These guard against two failure modes observed in real journal usage:
+
+1. The LLM emits ``task_titles`` referencing a task that's only in the
+   prep context — not actually mentioned by the user. Without a check,
+   every moment ends up linked to whatever's open in the user's queue.
+
+2. The LLM emits generic placeholder ``place_names`` like ``"work"`` /
+   ``"home"`` instead of real place notes. These role-labels aren't
+   places.
+
+Both are exercised through the pure helpers; full-stack handler tests
+would require a session-bound DB fixture this suite doesn't have yet.
+"""
+
+from unittest.mock import AsyncMock, patch
+
+import pytest
+
+
+def test_content_keywords_drops_stopwords_and_short_tokens():
+    from fabledassistant.services.tools.journal import _content_keywords
+
+    kw = _content_keywords(
+        "I went to the store to pick up milk and bread for the kids."
+    )
+    # Stopwords (the, to, for, and, i) gone; short tokens (kids? 4 chars - kept)
+    # filtered. Real content words kept.
+    assert "store" in kw
+    assert "milk" in kw
+    assert "bread" in kw
+    assert "kids" in kw
+    assert "the" not in kw
+    assert "to" not in kw
+    assert "for" not in kw
+    assert "i" not in kw
+
+
+def test_content_keywords_extracts_named_entities():
+    """Place names and project nouns survive tokenization. Short numeric
+    fragments (e.g. '14') get filtered alongside other <3-char tokens —
+    the surrounding alpha keywords carry the overlap weight in practice."""
+    from fabledassistant.services.tools.journal import _content_keywords
+
+    kw = _content_keywords("Migration prep at Branch 14 Bedford.")
+    assert "branch" in kw
+    assert "bedford" in kw
+    assert "migration" in kw
+
+
+def test_filter_placeholder_places_drops_generic_role_labels():
+    from fabledassistant.services.tools.journal import _filter_placeholder_places
+
+    kept, dropped = _filter_placeholder_places(
+        ["work", "Famous Supply", "home", "Branch 14 Bedford", "the office"]
+    )
+    assert "Famous Supply" in kept
+    assert "Branch 14 Bedford" in kept
+    assert "work" in dropped
+    assert "home" in dropped
+    assert "the office" in dropped
+
+
+def test_filter_placeholder_places_is_case_insensitive():
+    from fabledassistant.services.tools.journal import _filter_placeholder_places
+
+    kept, dropped = _filter_placeholder_places(["WORK", "Home", "OFFICE"])
+    assert kept == []
+    assert set(dropped) == {"WORK", "Home", "OFFICE"}
+
+
+def test_filter_placeholder_places_preserves_real_places_named_similarly():
+    """A user-defined place that happens to be ONE word but isn't a generic
+    role-label (e.g. 'Akron') stays."""
+    from fabledassistant.services.tools.journal import _filter_placeholder_places
+
+    kept, dropped = _filter_placeholder_places(["Akron", "Cleveland"])
+    assert kept == ["Akron", "Cleveland"]
+    assert dropped == []
+
+
+@pytest.mark.asyncio
+async def test_keyword_overlap_drops_unrelated_task_link():
+    """The reported failure mode: model attached Weston's ADHD task to a
+    Docker-swarm moment. With the keyword guard, the link gets dropped."""
+    from fabledassistant.services.tools.journal import (
+        _filter_task_ids_by_keyword_overlap,
+    )
+
+    # Mock the DB lookup to return the offending task title for id=2.
+    fake_session = AsyncMock()
+    fake_session.execute = AsyncMock()
+    fake_session.execute.return_value.all = lambda: [
+        (2, "Research Weston's ADHD Evaluation"),
+    ]
+    fake_session.__aenter__ = AsyncMock(return_value=fake_session)
+    fake_session.__aexit__ = AsyncMock(return_value=None)
+
+    with patch(
+        "fabledassistant.services.tools.journal.async_session",
+        return_value=fake_session,
+    ):
+        kept = await _filter_task_ids_by_keyword_overlap(
+            user_id=1,
+            content="Working on restaging Docker in the swarm; encountered network breakage on a Windows node.",
+            task_ids=[2],
+        )
+
+    assert kept == []
+
+
+@pytest.mark.asyncio
+async def test_keyword_overlap_keeps_genuinely_referenced_task():
+    """When the moment content shares a meaningful keyword with the task
+    title, the link is preserved."""
+    from fabledassistant.services.tools.journal import (
+        _filter_task_ids_by_keyword_overlap,
+    )
+
+    fake_session = AsyncMock()
+    fake_session.execute = AsyncMock()
+    fake_session.execute.return_value.all = lambda: [
+        (5, "Restage Docker on Fam-dockerwin04"),
+    ]
+    fake_session.__aenter__ = AsyncMock(return_value=fake_session)
+    fake_session.__aexit__ = AsyncMock(return_value=None)
+
+    with patch(
+        "fabledassistant.services.tools.journal.async_session",
+        return_value=fake_session,
+    ):
+        kept = await _filter_task_ids_by_keyword_overlap(
+            user_id=1,
+            content="Reinstalled Microsoft container support; Docker restage now works.",
+            task_ids=[5],
+        )
+
+    # 'docker' appears in both → keep
+    assert kept == [5]
+
+
+@pytest.mark.asyncio
+async def test_keyword_overlap_handles_partial_relevance():
+    """Mixed ids: keep the related one, drop the unrelated one."""
+    from fabledassistant.services.tools.journal import (
+        _filter_task_ids_by_keyword_overlap,
+    )
+
+    fake_session = AsyncMock()
+    fake_session.execute = AsyncMock()
+    fake_session.execute.return_value.all = lambda: [
+        (2, "Research Weston's ADHD Evaluation"),
+        (5, "Restage Docker on Fam-dockerwin04"),
+    ]
+    fake_session.__aenter__ = AsyncMock(return_value=fake_session)
+    fake_session.__aexit__ = AsyncMock(return_value=None)
+
+    with patch(
+        "fabledassistant.services.tools.journal.async_session",
+        return_value=fake_session,
+    ):
+        kept = await _filter_task_ids_by_keyword_overlap(
+            user_id=1,
+            content="Working on restaging Docker in the swarm.",
+            task_ids=[2, 5],
+        )
+
+    assert kept == [5]
+
+
+@pytest.mark.asyncio
+async def test_keyword_overlap_empty_task_ids_returns_empty():
+    from fabledassistant.services.tools.journal import (
+        _filter_task_ids_by_keyword_overlap,
+    )
+
+    kept = await _filter_task_ids_by_keyword_overlap(
+        user_id=1, content="anything", task_ids=[],
+    )
+    assert kept == []

tests/test_tool_use_fixes.py

@@ -0,0 +1,145 @@
+"""Tests for the tool-use fixes from the 2026-05-08 journal session."""
+
+from types import SimpleNamespace
+from unittest.mock import AsyncMock, patch
+
+import pytest
+
+
+def _project(pid: int, title: str, description: str = "", auto_summary: str = ""):
+    return SimpleNamespace(
+        id=pid, title=title, description=description, auto_summary=auto_summary,
+    )
+
+
+@pytest.mark.asyncio
+async def test_search_projects_tool_returns_success_true():
+    """The dispatcher sets status from result['success']; without this key
+    the call gets labeled 'error' even when data is returned."""
+    from fabledassistant.services.tools import projects as projects_tool
+
+    fake_projects = [_project(5, "Famous-Supply Work topics", "AT&T fiber circuit")]
+
+    # `list_projects` is imported locally inside search_projects_tool, so we
+    # patch the source module rather than the consumer.
+    with patch("fabledassistant.services.projects.list_projects", new=AsyncMock(return_value=fake_projects)):
+        result = await projects_tool.search_projects_tool(
+            user_id=1, arguments={"query": "famous supply"},
+        )
+
+    assert result["success"] is True
+    assert result["type"] == "projects_list"
+    assert len(result["data"]["projects"]) == 1
+
+
+def test_strip_type_nouns_removes_task_word():
+    from fabledassistant.services.notes import _strip_type_nouns
+    assert _strip_type_nouns("sebring secondary task") == ["sebring", "secondary"]
+
+
+def test_strip_type_nouns_removes_all_variants():
+    from fabledassistant.services.notes import _strip_type_nouns
+    assert _strip_type_nouns("project notes task") == []
+
+
+def test_strip_type_nouns_case_insensitive():
+    from fabledassistant.services.notes import _strip_type_nouns
+    assert _strip_type_nouns("Sebring Task NOTES") == ["Sebring"]
+
+
+def test_strip_type_nouns_preserves_real_content_words():
+    from fabledassistant.services.notes import _strip_type_nouns
+    assert _strip_type_nouns("circuit configuration") == ["circuit", "configuration"]
+
+
+def test_strip_type_nouns_handles_empty_string():
+    from fabledassistant.services.notes import _strip_type_nouns
+    assert _strip_type_nouns("") == []
+    assert _strip_type_nouns("   ") == []
+
+
+def test_score_project_match_exact_title_returns_1():
+    from fabledassistant.services.tools._helpers import score_project_match
+    p = _project(5, "Famous-Supply Work topics")
+    assert score_project_match("Famous-Supply Work topics", p) == 1.0
+
+
+def test_score_project_match_colloquial_substring_at_least_85():
+    """'famous supply' is a substring of normalized 'famous supply work topics'
+    after stripping the hyphen. Substring match returns 0.85."""
+    from fabledassistant.services.tools._helpers import score_project_match
+    p = _project(5, "Famous-Supply Work topics", auto_summary="AT&T fiber circuit")
+    score = score_project_match("famous supply project", p)
+    assert score >= 0.85, f"expected substring tier (>=0.85), got {score}"
+
+
+def test_score_project_match_query_in_summary_returns_70():
+    from fabledassistant.services.tools._helpers import score_project_match
+    p = _project(12, "Minstrel", auto_summary="self-hosted music server")
+    assert score_project_match("music server", p) == 0.70
+
+
+def test_score_project_match_unrelated_returns_low():
+    from fabledassistant.services.tools._helpers import score_project_match
+    p = _project(12, "Minstrel", auto_summary="self-hosted music server")
+    assert score_project_match("garden renovation", p) < 0.5
+
+
+def test_score_project_match_empty_query_returns_zero():
+    from fabledassistant.services.tools._helpers import score_project_match
+    p = _project(5, "Famous-Supply Work topics")
+    assert score_project_match("", p) == 0.0
+
+
+@pytest.mark.asyncio
+async def test_search_projects_tool_ranks_substring_match_above_others():
+    """Substring hits (score 0.85) must rank above SequenceMatcher misses
+    for unrelated projects."""
+    from fabledassistant.services.tools import projects as projects_tool
+
+    fake_projects = [
+        _project(12, "Minstrel", auto_summary="self-hosted music server"),
+        _project(5, "Famous-Supply Work topics", auto_summary="AT&T fiber circuit"),
+        _project(13, "ImageRepo", auto_summary="self-hosted Flask app"),
+    ]
+
+    with patch("fabledassistant.services.projects.list_projects", new=AsyncMock(return_value=fake_projects)):
+        result = await projects_tool.search_projects_tool(
+            user_id=1, arguments={"query": "famous supply project"},
+        )
+
+    top = result["data"]["projects"][0]
+    assert top["id"] == 5, f"expected Famous-Supply to rank first, got {top}"
+    assert top["score"] >= 0.85
+
+
+@pytest.mark.asyncio
+async def test_resolve_project_finds_colloquial_match(monkeypatch):
+    """resolve_project must surface 'Famous-Supply Work topics' when the
+    user passes 'famous supply project' — substring match via the shared
+    score helper, score 0.85 ≥ 0.55 threshold."""
+    from fabledassistant.services.tools import _helpers
+
+    fake_projects = [
+        _project(12, "Minstrel", auto_summary="self-hosted music server"),
+        _project(5, "Famous-Supply Work topics", auto_summary="AT&T fiber circuit"),
+    ]
+
+    async def fake_get_project_by_title(uid, name):
+        return None  # force the scored path
+
+    async def fake_list_projects(uid):
+        return fake_projects
+
+    monkeypatch.setattr(
+        "fabledassistant.services.projects.get_project_by_title",
+        fake_get_project_by_title,
+    )
+    monkeypatch.setattr(
+        "fabledassistant.services.projects.list_projects",
+        fake_list_projects,
+    )
+
+    result = await _helpers.resolve_project(user_id=1, project_name="famous supply project")
+    assert result is not None
+    assert result.id == 5