diff --git a/docs/design-system.md b/docs/design-system.md
index ab9f373..78e9df2 100644
--- a/docs/design-system.md
+++ b/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.*
diff --git a/fable-mcp/pyproject.toml b/fable-mcp/pyproject.toml
index d3212e8..ff90611 100644
--- a/fable-mcp/pyproject.toml
+++ b/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 = [
diff --git a/src/fabledassistant/services/journal_pipeline.py b/src/fabledassistant/services/journal_pipeline.py
index 0fa658c..35e5687 100644
--- a/src/fabledassistant/services/journal_pipeline.py
+++ b/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 +59,26 @@ 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.
+
 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 +111,15 @@ 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 +165,11 @@ 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 ""
diff --git a/src/fabledassistant/services/journal_prep.py b/src/fabledassistant/services/journal_prep.py
index ec7966a..73734ac 100644
--- a/src/fabledassistant/services/journal_prep.py
+++ b/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,
@@ -48,41 +108,71 @@ 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"] = []
@@ -148,22 +238,40 @@ 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 +350,12 @@ _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?\", "
diff --git a/src/fabledassistant/services/llm.py b/src/fabledassistant/services/llm.py
index 21238c6..316936a 100644
--- a/src/fabledassistant/services/llm.py
+++ b/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
@@ -678,7 +683,7 @@ 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
diff --git a/src/fabledassistant/services/tools/calendar.py b/src/fabledassistant/services/tools/calendar.py
index 90828e2..0218ddc 100644
--- a/src/fabledassistant/services/tools/calendar.py
+++ b/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 +78,86 @@ 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 _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."
+    ),
     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 +167,36 @@ 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:
@@ -168,18 +286,34 @@ 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."
+    ),
     parameters={
         "query": {"type": "string", "description": "Search term to find the event to update (matches against title)"},
         "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"],
 )
@@ -198,16 +332,24 @@ 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."}
diff --git a/src/fabledassistant/services/tools/journal.py b/src/fabledassistant/services/tools/journal.py
index 38cf416..42c2133 100644
--- a/src/fabledassistant/services/tools/journal.py
+++ b/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,
@@ -78,7 +170,16 @@ async def _resolve_entity_ids_by_name(
     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 +272,17 @@ 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 +307,15 @@ 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,
diff --git a/tests/test_calendar_tool_tz.py b/tests/test_calendar_tool_tz.py
index bab715f..71b0e24 100644
--- a/tests/test_calendar_tool_tz.py
+++ b/tests/test_calendar_tool_tz.py
@@ -132,3 +132,482 @@ 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
+
+
+@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
diff --git a/tests/test_journal_prep_filtering.py b/tests/test_journal_prep_filtering.py
new file mode 100644
index 0000000..58f68fe
--- /dev/null
+++ b/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
diff --git a/tests/test_record_moment_guards.py b/tests/test_record_moment_guards.py
new file mode 100644
index 0000000..2772dcd
--- /dev/null
+++ b/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 == []