app/api/routers/calendar.py

@@ -53,6 +53,7 @@ from app.services.agent_status import (
     transition_to_offline,
     transition_to_exhausted,
 )
+from app.services.discord_wakeup import create_private_wakeup_channel
 from app.services.minimum_workload import (
     get_workload_config,
     get_workload_warnings_for_date,
@@ -299,6 +300,45 @@ def _apply_agent_slot_update(slot: TimeSlot, payload: SlotAgentUpdate) -> None:
         slot.attended = True
 
 
+def _maybe_trigger_discord_wakeup(db: Session, slot: TimeSlot) -> dict | None:
+    """Trigger Discord wakeup if slot became ONGOING and not already sent."""
+    # Only trigger for ONGOING status and if not already sent
+    if slot.status != SlotStatus.ONGOING or slot.wakeup_sent_at is not None:
+        return None
+
+    # Get user and check for discord_user_id
+    user = db.query(User).filter(User.id == slot.user_id).first()
+    if not user or not user.discord_user_id:
+        return None
+
+    # Get agent for this user
+    agent = db.query(Agent).filter(Agent.user_id == user.id).first()
+    agent_id_str = agent.agent_id if agent else "unknown"
+
+    # Build wakeup message
+    title = f"HarborForge Slot: {slot.event_type.value if slot.event_type else 'work'}"
+    message = (
+        f"🎯 **Slot started**\n"
+        f"Agent: `{agent_id_str}`\n"
+        f"Type: {slot.slot_type.value}\n"
+        f"Duration: {slot.estimated_duration}min\n"
+        f"Priority: {slot.priority}\n"
+        f"Use `hf calendar slot {slot.id}` for details."
+    )
+
+    try:
+        result = create_private_wakeup_channel(
+            discord_user_id=user.discord_user_id,
+            title=title,
+            message=message,
+        )
+        slot.wakeup_sent_at = datetime.now(timezone.utc)
+        return {"ok": True, "channel_id": result.get("channel_id")}
+    except Exception as e:
+        # Log but don't fail the slot update
+        return {"ok": False, "error": str(e)}
+
+
 @router.api_route(
     "/agent/heartbeat",
     methods=["GET", "POST"],
@@ -338,6 +378,7 @@ def agent_update_real_slot(
     if slot is None:
         raise HTTPException(status_code=404, detail="Slot not found")
     _apply_agent_slot_update(slot, payload)
+    _maybe_trigger_discord_wakeup(db, slot)
     db.commit()
     db.refresh(slot)
     return TimeSlotEditResponse(slot=_slot_to_response(slot), warnings=[])
@@ -361,6 +402,7 @@ def agent_update_virtual_slot(
         db.rollback()
         raise HTTPException(status_code=404, detail="Slot not found")
     _apply_agent_slot_update(slot, payload)
+    _maybe_trigger_discord_wakeup(db, slot)
     db.commit()
     db.refresh(slot)
     return TimeSlotEditResponse(slot=_slot_to_response(slot), warnings=[])

app/main.py

@@ -42,6 +42,7 @@ def config_status():
         return {
             "initialized": cfg.get("initialized", False),
             "backend_url": cfg.get("backend_url"),
+            "discord": cfg.get("discord") or {},
         }
     except Exception:
         return {"initialized": False}
@@ -358,6 +359,10 @@ def _migrate_schema():
                 ) ENGINE=InnoDB DEFAULT CHARSET=utf8mb4
             """))
 
+        # --- time_slots: add wakeup_sent_at for Discord wakeup tracking ---
+        if _has_table(db, "time_slots") and not _has_column(db, "time_slots", "wakeup_sent_at"):
+            db.execute(text("ALTER TABLE time_slots ADD COLUMN wakeup_sent_at DATETIME NULL"))
+
         db.commit()
     except Exception as e:
         db.rollback()

app/models/calendar.py

@@ -165,6 +165,12 @@ class TimeSlot(Base):
         comment="Lifecycle status of this slot",
     )
 
+    wakeup_sent_at = Column(
+        DateTime(timezone=True),
+        nullable=True,
+        comment="When Discord wakeup was sent for this slot",
+    )
+
     plan_id = Column(
         Integer,
         ForeignKey("schedule_plans.id"),