diff --git a/alembic/versions/0013_note_label_via_tag.py b/alembic/versions/0013_note_label_via_tag.py
new file mode 100644
index 0000000..f3f1c09
--- /dev/null
+++ b/alembic/versions/0013_note_label_via_tag.py
@@ -0,0 +1,26 @@
+"""note_labels.via_tag
+
+Revision ID: 0013
+Revises: 0012
+Create Date: 2026-07-22
+"""
+from alembic import op
+import sqlalchemy as sa
+
+revision = "0013"
+down_revision = "0012"
+branch_labels = None
+depends_on = None
+
+
+def upgrade() -> None:
+    # Marks a note↔label attachment that came from a body #tag (vs. the picker).
+    # Existing attachments default to False = manual, which is correct.
+    op.add_column(
+        "note_labels",
+        sa.Column("via_tag", sa.Boolean(), nullable=False, server_default=sa.false()),
+    )
+
+
+def downgrade() -> None:
+    op.drop_column("note_labels", "via_tag")
diff --git a/frontend/src/components/LabelPicker.vue b/frontend/src/components/LabelPicker.vue
index 07f4d9e..e109d02 100644
--- a/frontend/src/components/LabelPicker.vue
+++ b/frontend/src/components/LabelPicker.vue
@@ -1,9 +1,12 @@
 <script setup lang="ts">
 import { computed, onBeforeUnmount, onMounted, ref } from "vue";
-import { useLabelsStore } from "../stores/labels";
+import { useLabelsStore, type Label } from "../stores/labels";
 import Icon from "./Icon.vue";
 import type { NoteLabel } from "../stores/notes";
 
+// A label attached via the picker is manual (via_tag: false).
+const asManual = (lb: Label): NoteLabel => ({ id: lb.id, name: lb.name, color: lb.color, via_tag: false });
+
 const props = defineProps<{ modelValue: NoteLabel[] }>();
 const emit = defineEmits<{ (e: "update:modelValue", value: NoteLabel[]): void }>();
 const labels = useLabelsStore();
@@ -21,17 +24,17 @@ const canCreate = computed(() => {
   return name.length > 0 && !labels.items.some((lb) => lb.name.toLowerCase() === name.toLowerCase());
 });
 
-function toggle(lb: NoteLabel) {
+function toggle(lb: Label) {
   const next = selectedIds.value.has(lb.id)
     ? props.modelValue.filter((x) => x.id !== lb.id)
-    : [...props.modelValue, lb];
+    : [...props.modelValue, asManual(lb)];
   emit("update:modelValue", next);
 }
 
 async function createAndAdd() {
   const created = await labels.create(filter.value.trim());
   filter.value = "";
-  if (!selectedIds.value.has(created.id)) emit("update:modelValue", [...props.modelValue, created]);
+  if (!selectedIds.value.has(created.id)) emit("update:modelValue", [...props.modelValue, asManual(created)]);
 }
 
 function onDocMousedown(e: MouseEvent) {
diff --git a/frontend/src/components/NoteCard.vue b/frontend/src/components/NoteCard.vue
index 5329339..692fc2b 100644
--- a/frontend/src/components/NoteCard.vue
+++ b/frontend/src/components/NoteCard.vue
@@ -188,7 +188,7 @@ onBeforeUnmount(() => document.removeEventListener("mousedown", onDocMousedown))
         :key="lb.id"
         class="rounded-full px-2 py-0.5 text-xs"
         :class="labelChip(lb.color)"
-        >{{ lb.name }}</span
+        >{{ lb.via_tag ? "#" + lb.name : lb.name }}</span
       >
     </div>
 
diff --git a/frontend/src/components/NoteEditor.vue b/frontend/src/components/NoteEditor.vue
index f38af5b..966b8b5 100644
--- a/frontend/src/components/NoteEditor.vue
+++ b/frontend/src/components/NoteEditor.vue
@@ -184,10 +184,15 @@ function onReminderChange(e: Event) {
 }
 
 async function onLabelsChange(next: NoteLabel[]) {
-  labelList.value = next;
+  // Tag-sourced labels are governed by the note body, not the picker — always keep
+  // them so a picker save can't strip a label the #tag still mandates.
+  const tagLabels = labelList.value.filter((lb) => lb.via_tag);
+  const tagIds = new Set(tagLabels.map((lb) => lb.id));
+  const merged = [...next.filter((lb) => !tagIds.has(lb.id)), ...tagLabels];
+  labelList.value = merged;
   await notes.setLabels(
     props.note.id,
-    next.map((lb) => lb.id),
+    merged.map((lb) => lb.id),
   );
 }
 
@@ -341,8 +346,9 @@ async function act(fn: () => Promise<void>) {
             class="inline-flex items-center gap-1 rounded-full px-2 py-0.5 text-xs"
             :class="labelChip(lb.color)"
           >
-            {{ lb.name }}
+            {{ lb.via_tag ? "#" + lb.name : lb.name }}
             <button
+              v-if="!lb.via_tag"
               type="button"
               class="text-neutral-400 hover:text-neutral-700 dark:hover:text-neutral-100"
               :aria-label="`Remove ${lb.name}`"
diff --git a/frontend/src/stores/notes.ts b/frontend/src/stores/notes.ts
index c8c2fc5..1f0ba30 100644
--- a/frontend/src/stores/notes.ts
+++ b/frontend/src/stores/notes.ts
@@ -11,6 +11,9 @@ export interface NoteLabel {
   id: string;
   name: string;
   color: string;
+  // True when this label is attached because of a #tag in the note body (kept in
+  // sync with the text); false = added manually via the picker.
+  via_tag: boolean;
 }
 
 export interface ChecklistItem {
diff --git a/src/thoughtsync/models/label.py b/src/thoughtsync/models/label.py
index 2f6fdb0..91ea2b0 100644
--- a/src/thoughtsync/models/label.py
+++ b/src/thoughtsync/models/label.py
@@ -3,7 +3,7 @@ from __future__ import annotations
 import uuid
 from datetime import datetime
 
-from sqlalchemy import DateTime, ForeignKey, Text, UniqueConstraint, func
+from sqlalchemy import Boolean, DateTime, ForeignKey, Text, UniqueConstraint, func
 from sqlalchemy.dialects.postgresql import UUID
 from sqlalchemy.orm import Mapped, mapped_column
 
@@ -34,3 +34,6 @@ class NoteLabel(Base):
     label_id: Mapped[uuid.UUID] = mapped_column(
         UUID(as_uuid=True), ForeignKey("labels.id", ondelete="CASCADE"), primary_key=True
     )
+    # True when this attachment came from a #tag in the note body (kept in sync with
+    # the body); False = added manually via the label picker (independent of #tags).
+    via_tag: Mapped[bool] = mapped_column(Boolean(), nullable=False, server_default=func.false())
diff --git a/src/thoughtsync/notes.py b/src/thoughtsync/notes.py
index 87b0a74..e5c2437 100644
--- a/src/thoughtsync/notes.py
+++ b/src/thoughtsync/notes.py
@@ -22,6 +22,29 @@ ALLOWED_IMAGE_MIMES = {"image/png": ".png", "image/jpeg": ".jpg", "image/gif": "
 
 _LINK_RE = re.compile(r"\[\[([^\[\]]+)\]\]")
 
+# A #tag: `#` at the start of the body or after whitespace, then a word char and
+# word chars/hyphens. A URL fragment (foo#bar) or mid-word `#` is not preceded by
+# whitespace, so it won't match.
+_TAG_RE = re.compile(r"(?:^|(?<=\s))#(\w[\w-]*)")
+
+
+def parse_tags(body: str | None) -> list[str]:
+    """Distinct #hashtags from a note body, in order, deduped case-insensitively.
+    A tag must contain a letter, so #2024 or #_ are ignored (avoids numeric noise)."""
+    if not body:
+        return []
+    out: list[str] = []
+    seen: set[str] = set()
+    for match in _TAG_RE.finditer(body):
+        tag = match.group(1)
+        if not any(c.isalpha() for c in tag):
+            continue
+        norm = tag.lower()
+        if norm not in seen:
+            seen.add(norm)
+            out.append(tag)
+    return out
+
 
 def parse_link_titles(body: str | None) -> list[str]:
     """Extract distinct normalized [[wiki-link]] titles from a note body."""
@@ -85,13 +108,15 @@ async def _labels_for_notes(db, note_ids: list) -> dict:
     if not note_ids:
         return result
     rows = await db.execute(
-        select(NoteLabel.note_id, Label.id, Label.name, Label.color)
+        select(NoteLabel.note_id, Label.id, Label.name, Label.color, NoteLabel.via_tag)
         .join(Label, Label.id == NoteLabel.label_id)
         .where(NoteLabel.note_id.in_(note_ids))
         .order_by(Label.name)
     )
-    for note_id, label_id, name, color in rows.all():
-        result.setdefault(note_id, []).append({"id": str(label_id), "name": name, "color": color})
+    for note_id, label_id, name, color, via_tag in rows.all():
+        result.setdefault(note_id, []).append(
+            {"id": str(label_id), "name": name, "color": color, "via_tag": via_tag}
+        )
     return result
 
 
@@ -176,6 +201,41 @@ async def _rewrite_links(db, note: Note) -> None:
         db.add(NoteLink(source_id=note.id, target_norm=norm))
 
 
+async def _find_or_create_label(db, owner_id, name: str):
+    """Owner's label id for `name` (case-insensitive match), creating it if absent."""
+    existing = await db.scalar(
+        select(Label.id).where(Label.owner_id == owner_id, func.lower(Label.name) == name.lower())
+    )
+    if existing is not None:
+        return existing
+    label = Label(owner_id=owner_id, name=name)
+    db.add(label)
+    await db.flush()
+    return label.id
+
+
+async def _reconcile_tags(db, note: Note) -> None:
+    """Sync tag-sourced labels (via_tag=True) with the #hashtags in the note body:
+    attach labels for current tags, detach tag-labels whose #tag was removed. Manual
+    picker labels (via_tag=False) are never touched."""
+    tag_label_ids: set = set()
+    for name in parse_tags(note.body):
+        tag_label_ids.add(await _find_or_create_label(db, note.owner_id, name))
+    rows = (await db.scalars(select(NoteLabel).where(NoteLabel.note_id == note.id))).all()
+    attached_ids = {r.label_id for r in rows}
+    # Detach tag-labels no longer backed by a #tag in the body.
+    for r in rows:
+        if r.via_tag and r.label_id not in tag_label_ids:
+            await db.delete(r)
+            attached_ids.discard(r.label_id)
+    # Attach new tags — skip labels already attached (in any form) to respect the PK
+    # and leave a manually-added label of the same name as-is.
+    for lid in tag_label_ids:
+        if lid not in attached_ids:
+            db.add(NoteLabel(note_id=note.id, label_id=lid, via_tag=True))
+            attached_ids.add(lid)
+
+
 def rewrite_link_title(body: str | None, old_norm: str, new_title: str) -> str:
     """Repoint every [[token]] whose normalized form == old_norm to [[new_title]]."""
     if not body:
@@ -425,6 +485,7 @@ async def create_note():
         for pos, text in enumerate(item_texts):
             db.add(NoteItem(note_id=note.id, text=text, position=pos))
         await _rewrite_links(db, note)
+        await _reconcile_tags(db, note)
         await db.commit()
         await db.refresh(note)
         return jsonify(await _serialize_note(db, note)), 201
@@ -483,6 +544,7 @@ async def update_note(note_id: str):
             note.display_title = derive_display_title(note.title, note.body)
         if "body" in data:
             await _rewrite_links(db, note)
+            await _reconcile_tags(db, note)
         # The display NAME changing — via an explicit title OR the first body line —
         # repoints inbound [[Old Name]] references so backlinks survive (skip pure
         # case/whitespace changes, which still resolve).
@@ -520,11 +582,17 @@ async def set_note_labels(note_id: str):
                     )
                 ).all()
             )
-        # Replace the note's label set with the (validated, owned) ids provided.
-        await db.execute(delete(NoteLabel).where(NoteLabel.note_id == note.id))
-        for lid in label_ids:
-            if lid in owned:
-                db.add(NoteLabel(note_id=note.id, label_id=lid))
+        # The picker manages MANUAL labels only; tag-sourced (via_tag=True) rows are
+        # governed by the body #tags and must survive a picker save.
+        chosen = {lid for lid in label_ids if lid in owned}
+        existing = (await db.scalars(select(NoteLabel).where(NoteLabel.note_id == note.id))).all()
+        attached_ids = {r.label_id for r in existing}
+        for r in existing:
+            if not r.via_tag and r.label_id not in chosen:
+                await db.delete(r)
+        for lid in chosen:
+            if lid not in attached_ids:
+                db.add(NoteLabel(note_id=note.id, label_id=lid, via_tag=False))
         await db.commit()
         return jsonify(await _serialize_note(db, note))
 
diff --git a/tests/test_notes.py b/tests/test_notes.py
index ff37129..e6d3e00 100644
--- a/tests/test_notes.py
+++ b/tests/test_notes.py
@@ -9,6 +9,7 @@ from thoughtsync.notes import (
     normalize_color,
     parse_link_titles,
     parse_list_items,
+    parse_tags,
     rewrite_link_title,
 )
 
@@ -131,6 +132,16 @@ def test_derive_display_title_caps_length():
     assert derive_display_title(long, "body") == "x" * 200
 
 
+def test_parse_tags():
+    assert parse_tags("buy milk #groceries and #to-do now") == ["groceries", "to-do"]
+    # case-insensitive dedup, first spelling wins
+    assert parse_tags("#Work then #work") == ["Work"]
+    # url fragments, mid-word #, purely-numeric, and a bare # are not tags
+    assert parse_tags("frag http://x/#nope mid#word #2024 #") == []
+    assert parse_tags(None) == []
+    assert parse_tags("#a #b #a") == ["a", "b"]
+
+
 def test_parse_list_items():
     assert parse_list_items(["milk", " eggs ", "", "   ", "bread"]) == ["milk", "eggs", "bread"]
     assert parse_list_items("not a list") == []