diff --git a/src/hqt/sessions/service.py b/src/hqt/sessions/service.py
index 84395fc..1f4579c 100644
--- a/src/hqt/sessions/service.py
+++ b/src/hqt/sessions/service.py
@@ -423,7 +423,8 @@ class SessionService:
         self, session_id: int, prompt: str, due_at: datetime
     ) -> ScheduledPrompt:
         """Create or replace the pending scheduled prompt for a session."""
-        if not prompt.strip():
+        prompt = prompt.strip()
+        if not prompt:
             raise ServiceError("Prompt cannot be empty")
         with self.factory() as db:
             sess = db.get(Session, session_id)
@@ -504,6 +505,11 @@ class SessionService:
                     force,
                 )
 
+            scheduled = (
+                db.query(ScheduledPrompt).filter_by(session_id=session_id).one_or_none()
+            )
+            if scheduled is not None:
+                db.delete(scheduled)
             db.delete(sess)
             db.commit()
 
diff --git a/tests/test_sessions.py b/tests/test_sessions.py
index e3f5d04..d645222 100644
--- a/tests/test_sessions.py
+++ b/tests/test_sessions.py
@@ -100,7 +100,7 @@ def test_schedule_prompt_creates_pending_row(service, db):
     sess = _seed_session(db)
     due_at = datetime(2026, 6, 11, 12)
 
-    prompt = service.schedule_prompt(sess.id, "run the tests", due_at)
+    prompt = service.schedule_prompt(sess.id, "  run the tests  ", due_at)
 
     assert prompt.session_id == sess.id
     assert prompt.prompt == "run the tests"
@@ -704,6 +704,27 @@ async def test_sync_window_labels_covers_all_projects(factory, db, tmux, harness
     assert labelled == {"hqt-1", "hqt-2"}
 
 
+@pytest.mark.asyncio
+async def test_sync_window_labels_includes_pending_scheduled_prompt(
+    factory, db, tmux, harnesses
+):
+    """sync_window_labels returns SessionInfo with pending scheduled prompt metadata."""
+    from hqt.tmux.runner import WindowInfo
+
+    service = SessionService(factory=factory, tmux=tmux, harnesses=harnesses)
+    result = await service.create_session(project_id=1, harness_name="claude-code")
+    due_at = datetime(2026, 6, 11, 12)
+    service.schedule_prompt(result.session.id, "run the tests", due_at)
+    tmux.poll_info.return_value = {"hqt-1": WindowInfo(alive=False, last_activity=0)}
+    tmux.set_window_label = AsyncMock()
+
+    infos = await service.sync_window_labels()
+
+    assert infos[0].scheduled_prompt is not None
+    assert infos[0].scheduled_prompt.prompt == "run the tests"
+    assert infos[0].scheduled_prompt.status == "pending"
+
+
 # ---------------------------------------------------------------------------
 # Item 3: real-configurator integration-seam test
 # ---------------------------------------------------------------------------
@@ -1499,6 +1520,20 @@ async def test_delete_session_remove_worktree_false_skips_removal(
     assert db.get(Session, sess_id) is None
 
 
+@pytest.mark.asyncio
+async def test_delete_session_deletes_scheduled_prompt(service, db):
+    sess = _seed_session(db)
+    sess_id = sess.id
+    due_at = datetime(2026, 6, 11, 12)
+    service.schedule_prompt(sess_id, "run the tests", due_at)
+
+    await service.delete_session(sess_id)
+
+    db.expire_all()
+    assert db.get(Session, sess_id) is None
+    assert db.query(ScheduledPrompt).filter_by(session_id=sess_id).one_or_none() is None
+
+
 @pytest.mark.asyncio
 async def test_worktree_state_for_plain_session_returns_none(
     service, db, tmux, harnesses, fake_worktree