Harden CalDAV write-back with retries (#1193)

Co-authored-by: Alexandre Teixeira <111787685+alteixeira20@users.noreply.github.com>

core/database.py

@@ -1602,6 +1602,7 @@ class CalendarCal(TimestampMixin, Base):
     # NULL for local calendars and for CalDAV calendars created before
     # multi-account support was added (treated as "use any configured account").
     account_id = Column(String, nullable=True, index=True)
+    caldav_base_url = Column(String, nullable=True)
 
     events = relationship("CalendarEvent", back_populates="calendar", cascade="all, delete-orphan")
 
@@ -1632,10 +1633,27 @@ class CalendarEvent(TimestampMixin, Base):
     # vanishes upstream). NULL/local = created locally (agent, email triage, or
     # a UI event whose write-back failed) and must NOT be pruned by the sync.
     origin      = Column(String, nullable=True, index=True)
+    remote_href = Column(String, nullable=True)        # CalDAV object URL for updates/deletes
+    remote_etag = Column(String, nullable=True)        # Last seen CalDAV ETag, when available
+    caldav_sync_pending = Column(String, nullable=True) # create | update | delete retry marker
 
     calendar = relationship("CalendarCal", back_populates="events")
 
 
+class CalendarDeletedEvent(TimestampMixin, Base):
+    """Hidden CalDAV delete tombstone retained until remote delete succeeds."""
+    __tablename__ = "caldav_deleted_events"
+
+    uid = Column(String, primary_key=True, index=True)
+    owner = Column(String, nullable=True, index=True)
+    calendar_id = Column(String, nullable=True, index=True)
+    remote_href = Column(String, nullable=True)
+    remote_etag = Column(String, nullable=True)
+    caldav_base_url = Column(String, nullable=True)
+    summary = Column(String, nullable=True)
+    last_error = Column(Text, nullable=True)
+
+
 class Integration(TimestampMixin, Base):
     """An external service connection (email, RSS, webhook, etc.)."""
     __tablename__ = "integrations"
@@ -1767,6 +1785,7 @@ def init_db():
     _migrate_add_calendar_is_utc()
     _migrate_add_calendar_origin()
     _migrate_add_calendar_account_id()
+    _migrate_add_caldav_sync_columns()
     _migrate_chat_messages_fts()
     _migrate_encrypt_email_passwords()
     _migrate_encrypt_signatures()
@@ -2067,6 +2086,31 @@ def _migrate_add_calendar_account_id():
             pass
 
 
+def _migrate_add_caldav_sync_columns():
+    """Add remote CalDAV metadata used for bidirectional sync."""
+    import sqlite3
+    db_path = DATABASE_URL.replace("sqlite:///", "")
+    if not os.path.exists(db_path):
+        return
+    try:
+        conn = sqlite3.connect(db_path)
+        ev_columns = [row[1] for row in conn.execute("PRAGMA table_info(calendar_events)").fetchall()]
+        if ev_columns and "remote_href" not in ev_columns:
+            conn.execute("ALTER TABLE calendar_events ADD COLUMN remote_href TEXT")
+        if ev_columns and "remote_etag" not in ev_columns:
+            conn.execute("ALTER TABLE calendar_events ADD COLUMN remote_etag TEXT")
+        if ev_columns and "caldav_sync_pending" not in ev_columns:
+            conn.execute("ALTER TABLE calendar_events ADD COLUMN caldav_sync_pending TEXT")
+
+        cal_columns = [row[1] for row in conn.execute("PRAGMA table_info(calendars)").fetchall()]
+        if cal_columns and "caldav_base_url" not in cal_columns:
+            conn.execute("ALTER TABLE calendars ADD COLUMN caldav_base_url TEXT")
+        conn.commit()
+        conn.close()
+    except Exception as e:
+        logging.getLogger(__name__).warning(f"CalDAV sync metadata migration failed: {e}")
+
+
 def _migrate_add_calendar_metadata():
     """Add importance/event_type/last_pinged columns to calendar_events table."""
     import sqlite3

routes/calendar_routes.py

@@ -11,7 +11,7 @@ from pydantic import BaseModel
 from sqlalchemy import or_, and_
 from dateutil.rrule import rrulestr
 
-from core.database import SessionLocal, CalendarCal, CalendarEvent
+from core.database import SessionLocal, CalendarCal, CalendarDeletedEvent, CalendarEvent
 from src.auth_helpers import require_user
 from src.upload_limits import read_upload_limited, ICS_MAX_BYTES
 
@@ -126,6 +126,54 @@ def _resolve_base_uid(uid: str) -> str:
         raise ValueError("malformed compound UID: missing base before ::")
     return base
 
+
+async def _push_caldav_event_after_commit(owner: str, uid: str, action: str):
+    """Best-effort CalDAV write-through. Local writes stay authoritative if
+    the remote server is unreachable; pending flags let /sync retry later."""
+    try:
+        result = {"ok": True}
+        if action == "create":
+            from src.caldav_sync import push_event_create
+            result = await push_event_create(owner, uid)
+        elif action == "update":
+            from src.caldav_sync import push_event_update
+            result = await push_event_update(owner, uid)
+        elif action == "delete":
+            from src.caldav_sync import push_event_delete
+            result = await push_event_delete(owner, uid)
+        if result and not result.get("ok") and not result.get("skipped"):
+            raise RuntimeError(result.get("error") or result)
+    except Exception as e:
+        logger.warning("CalDAV %s push failed for uid=%s: %s", action, uid, e)
+        if action in {"create", "update"}:
+            db = SessionLocal()
+            try:
+                ev = _get_or_404_event(db, uid, owner)
+                ev.caldav_sync_pending = action
+                db.commit()
+            except Exception:
+                db.rollback()
+            finally:
+                db.close()
+
+
+def _record_caldav_delete_tombstone(db, ev: CalendarEvent, owner: str) -> None:
+    if not (ev.calendar and ev.calendar.source == "caldav"):
+        return
+    tombstone = db.query(CalendarDeletedEvent).filter(
+        CalendarDeletedEvent.uid == ev.uid,
+        CalendarDeletedEvent.owner == owner,
+    ).first()
+    if not tombstone:
+        tombstone = CalendarDeletedEvent(uid=ev.uid, owner=owner)
+        db.add(tombstone)
+    tombstone.calendar_id = ev.calendar_id
+    tombstone.remote_href = ev.remote_href
+    tombstone.remote_etag = ev.remote_etag
+    tombstone.caldav_base_url = getattr(ev.calendar, "caldav_base_url", None)
+    tombstone.summary = ev.summary or ""
+    tombstone.last_error = None
+
 # ── Pydantic models ──
 
 class EventCreate(BaseModel):
@@ -843,13 +891,13 @@ def setup_calendar_routes() -> APIRouter:
             return {"ok": False, "error": str(e)[:200]}
 
     @router.post("/sync")
-    async def sync_caldav_endpoint(request: Request):
-        """Pull events from the configured CalDAV server into local DB.
+    async def sync_caldav_endpoint(request: Request, direction: str = "pull"):
+        """Sync events with the configured CalDAV server.
         Returns counts + any per-calendar errors. Called by the frontend
         on calendar open and by the periodic scheduler loop."""
         owner = _require_user(request)
-        from src.caldav_sync import sync_caldav
-        return await sync_caldav(owner)
+        from src.caldav_sync import sync_caldav_direction
+        return await sync_caldav_direction(owner, direction)
 
 
     @router.delete("/calendars/{cal_id}")
@@ -1002,19 +1050,12 @@ def setup_calendar_routes() -> APIRouter:
                 is_utc=_is_utc and not data.all_day,
                 rrule=data.rrule or "",
                 color=data.color or None,
+                caldav_sync_pending="create" if cal.source == "caldav" else None,
             )
             db.add(ev)
             db.commit()
             if cal.source == "caldav":
-                # Push the new event to the remote so it appears on the user's
-                # other devices — the sync is otherwise pull-only (#800).
-                from src.caldav_writeback import writeback_event
-                await writeback_event(owner, cal.source, cal.id, {
-                    "uid": uid, "summary": data.summary, "description": data.description,
-                    "location": data.location, "dtstart": dtstart, "dtend": dtend,
-                    "all_day": data.all_day, "is_utc": _is_utc and not data.all_day,
-                    "rrule": data.rrule or "",
-                })
+                await _push_caldav_event_after_commit(owner, uid, "create")
             return {"ok": True, "uid": uid}
         except HTTPException:
             raise
@@ -1060,15 +1101,12 @@ def setup_calendar_routes() -> APIRouter:
                 ev.rrule = data.rrule
             if data.color is not None:
                 ev.color = data.color if data.color else None
+            is_caldav = ev.calendar and ev.calendar.source == "caldav"
+            if is_caldav:
+                ev.caldav_sync_pending = "update"
             db.commit()
-            cal = db.query(CalendarCal).filter(CalendarCal.id == ev.calendar_id).first()
-            if cal and cal.source == "caldav":
-                from src.caldav_writeback import writeback_event
-                await writeback_event(owner, cal.source, cal.id, {
-                    "uid": ev.uid, "summary": ev.summary, "description": ev.description,
-                    "location": ev.location, "dtstart": ev.dtstart, "dtend": ev.dtend,
-                    "all_day": ev.all_day, "is_utc": ev.is_utc, "rrule": ev.rrule or "",
-                })
+            if is_caldav:
+                await _push_caldav_event_after_commit(owner, base_uid, "update")
             return {"ok": True}
         except HTTPException:
             raise
@@ -1089,15 +1127,13 @@ def setup_calendar_routes() -> APIRouter:
         db = SessionLocal()
         try:
             ev = _get_or_404_event(db, base_uid, owner)
-            # Capture what the remote push needs BEFORE the row is gone.
-            _cal = db.query(CalendarCal).filter(CalendarCal.id == ev.calendar_id).first()
-            _is_caldav = bool(_cal and _cal.source == "caldav")
-            _cal_id, _ev_uid = ev.calendar_id, ev.uid
+            is_caldav = ev.calendar and ev.calendar.source == "caldav"
+            if is_caldav:
+                _record_caldav_delete_tombstone(db, ev, owner)
             db.delete(ev)
             db.commit()
-            if _is_caldav:
-                from src.caldav_writeback import writeback_event
-                await writeback_event(owner, "caldav", _cal_id, {"uid": _ev_uid}, delete=True)
+            if is_caldav:
+                await _push_caldav_event_after_commit(owner, base_uid, "delete")
             return {"ok": True}
         except HTTPException:
             raise

src/caldav_sync.py

@@ -128,6 +128,17 @@ def validate_caldav_url(raw_url: str) -> str:
     return urlunparse(parsed._replace(fragment="")).rstrip("/")
 
 
+def _event_etag(obj) -> str:
+    """Best-effort ETag extraction from python-caldav resources."""
+    try:
+        etag = getattr(obj, "etag", None)
+        if callable(etag):
+            etag = etag()
+        return str(etag or "")
+    except Exception:
+        return ""
+
+
 def _stable_cal_id(remote_url: str, owner: str = "", account_id: str = "") -> str:
     """Deterministic local id for a remote CalDAV calendar, scoped to owner
     and account so two users — or one user with two accounts — pointing at
@@ -316,11 +327,12 @@ def _sync_blocking(owner: str, url: str, username: str, password: str, account_i
                         color="#5b8abf",
                         source="caldav",
                         account_id=account_id or None,
+                        caldav_base_url=remote_url,
                     )
                     db.add(local_cal)
                     db.commit()
                 else:
-                    # Refresh display name and stamp account_id if missing.
+                    # Refresh display name and stamp CalDAV metadata if missing.
                     changed = False
                     if local_cal.name != display_name:
                         local_cal.name = display_name
@@ -328,6 +340,9 @@ def _sync_blocking(owner: str, url: str, username: str, password: str, account_i
                     if account_id and not local_cal.account_id:
                         local_cal.account_id = account_id
                         changed = True
+                    if local_cal.caldav_base_url != remote_url:
+                        local_cal.caldav_base_url = remote_url
+                        changed = True
                     if changed:
                         db.commit()
                 result["calendars"] += 1
@@ -395,6 +410,9 @@ def _sync_blocking(owner: str, url: str, username: str, password: str, account_i
 
                         existing = _find_existing_event(db, pending, uid_val, local_cal.id)
                         if existing:
+                            if existing.caldav_sync_pending in {"create", "update"}:
+                                result["events"] += 1
+                                continue
                             existing.calendar_id = local_cal.id
                             existing.summary = summary
                             existing.description = description
@@ -405,6 +423,9 @@ def _sync_blocking(owner: str, url: str, username: str, password: str, account_i
                             existing.is_utc = row_is_utc
                             existing.rrule = rrule
                             existing.origin = "caldav"
+                            existing.remote_href = str(getattr(obj, "url", "") or "") or None
+                            existing.remote_etag = _event_etag(obj) or None
+                            existing.caldav_sync_pending = None
                         else:
                             new_ev = CalendarEvent(
                                 uid=uid_val,
@@ -418,6 +439,8 @@ def _sync_blocking(owner: str, url: str, username: str, password: str, account_i
                                 is_utc=row_is_utc,
                                 rrule=rrule,
                                 origin="caldav",
+                                remote_href=str(getattr(obj, "url", "") or "") or None,
+                                remote_etag=_event_etag(obj) or None,
                             )
                             db.add(new_ev)
                             pending[uid_val] = new_ev
@@ -442,6 +465,8 @@ def _sync_blocking(owner: str, url: str, username: str, password: str, account_i
                         CalendarEvent.origin == "caldav",
                         CalendarEvent.dtstart >= start,
                         CalendarEvent.dtstart <= end,
+                        CalendarEvent.remote_href.isnot(None),
+                        CalendarEvent.caldav_sync_pending.is_(None),
                         ~CalendarEvent.uid.in_(seen_uids) if seen_uids else CalendarEvent.uid.isnot(None),
                     ).all()
                     for ev in stale:
@@ -458,6 +483,92 @@ def _sync_blocking(owner: str, url: str, username: str, password: str, account_i
     return result
 
 
+def _event_payload(ev) -> dict:
+    return {
+        "uid": ev.uid,
+        "summary": ev.summary,
+        "description": ev.description,
+        "location": ev.location,
+        "dtstart": ev.dtstart,
+        "dtend": ev.dtend,
+        "all_day": ev.all_day,
+        "is_utc": ev.is_utc,
+        "rrule": ev.rrule or "",
+    }
+
+
+def _load_event_for_writeback(owner: str, uid: str) -> tuple[str, str, dict] | None:
+    from core.database import CalendarCal, CalendarEvent, SessionLocal
+
+    db = SessionLocal()
+    try:
+        ev = (
+            db.query(CalendarEvent)
+            .join(CalendarCal)
+            .filter(CalendarEvent.uid == uid, CalendarCal.owner == owner)
+            .first()
+        )
+        if not ev or not ev.calendar or ev.calendar.source != "caldav":
+            return None
+        return ev.calendar.source, ev.calendar.id, _event_payload(ev)
+    finally:
+        db.close()
+
+
+def _load_delete_for_writeback(owner: str, uid: str) -> tuple[str, str, dict] | None:
+    from core.database import CalendarCal, CalendarDeletedEvent, CalendarEvent, SessionLocal
+
+    db = SessionLocal()
+    try:
+        tombstone = db.query(CalendarDeletedEvent).filter(
+            CalendarDeletedEvent.uid == uid,
+            CalendarDeletedEvent.owner == owner,
+        ).first()
+        if tombstone:
+            return "caldav", tombstone.calendar_id, {"uid": uid}
+
+        ev = (
+            db.query(CalendarEvent)
+            .join(CalendarCal)
+            .filter(CalendarEvent.uid == uid, CalendarCal.owner == owner)
+            .first()
+        )
+        if not ev or not ev.calendar or ev.calendar.source != "caldav":
+            return None
+        return ev.calendar.source, ev.calendar.id, {"uid": uid}
+    finally:
+        db.close()
+
+
+def _pending_writeback_uids(owner: str) -> tuple[list[str], list[str]]:
+    from core.database import CalendarCal, CalendarDeletedEvent, CalendarEvent, SessionLocal
+
+    db = SessionLocal()
+    try:
+        rows = (
+            db.query(CalendarEvent.uid)
+            .join(CalendarCal)
+            .filter(
+                CalendarCal.owner == owner,
+                CalendarCal.source == "caldav",
+                CalendarEvent.status != "cancelled",
+                (
+                    (CalendarEvent.caldav_sync_pending.isnot(None))
+                    | (CalendarEvent.remote_href.is_(None))
+                ),
+            )
+            .all()
+        )
+        delete_rows = (
+            db.query(CalendarDeletedEvent.uid)
+            .filter(CalendarDeletedEvent.owner == owner)
+            .all()
+        )
+        return [row[0] for row in rows], [row[0] for row in delete_rows]
+    finally:
+        db.close()
+
+
 def _load_caldav_accounts(owner: str) -> list:
     """Return the list of CalDAV accounts for *owner*, auto-migrating the legacy
     single-account ``caldav`` key to the new ``caldav_accounts`` list on first call.
@@ -533,3 +644,69 @@ async def sync_caldav(owner: str) -> dict:
         for err in result.get("errors", []):
             totals["errors"].append(f"{label}: {err}")
     return totals
+
+
+async def push_event_create(owner: str, uid: str) -> dict:
+    loaded = _load_event_for_writeback(owner, uid)
+    if not loaded:
+        return {"ok": True, "skipped": True}
+    source, calendar_id, payload = loaded
+    from src.caldav_writeback import writeback_event
+    return await writeback_event(owner, source, calendar_id, payload)
+
+
+async def push_event_update(owner: str, uid: str) -> dict:
+    return await push_event_create(owner, uid)
+
+
+async def push_event_delete(owner: str, uid: str) -> dict:
+    loaded = _load_delete_for_writeback(owner, uid)
+    if not loaded:
+        return {"ok": True, "skipped": True}
+    source, calendar_id, payload = loaded
+    from src.caldav_writeback import writeback_event
+    return await writeback_event(owner, source, calendar_id, payload, delete=True)
+
+
+async def push_pending_events(owner: str) -> dict:
+    result = {"events": 0, "errors": []}
+    uids, delete_uids = _pending_writeback_uids(owner)
+    for event_uid in uids:
+        try:
+            out = await push_event_update(owner, event_uid)
+            if out.get("ok"):
+                result["events"] += 1
+            elif not out.get("skipped"):
+                result["errors"].append(f"{event_uid}: {str(out.get('error') or out)[:160]}")
+        except Exception as e:
+            logger.warning("CalDAV pending push failed for uid=%s: %s", event_uid, e)
+            result["errors"].append(f"{event_uid}: {str(e)[:160]}")
+    for event_uid in delete_uids:
+        try:
+            out = await push_event_delete(owner, event_uid)
+            if out.get("ok"):
+                result["events"] += 1
+            elif not out.get("skipped"):
+                result["errors"].append(f"{event_uid}: {str(out.get('error') or out)[:160]}")
+        except Exception as e:
+            logger.warning("CalDAV pending delete failed for uid=%s: %s", event_uid, e)
+            result["errors"].append(f"{event_uid}: {str(e)[:160]}")
+    return result
+
+
+async def sync_caldav_direction(owner: str, direction: str = "pull") -> dict:
+    direction = (direction or "pull").strip().lower()
+    if direction == "pull":
+        return await sync_caldav(owner)
+    if direction == "push":
+        return await push_pending_events(owner)
+    if direction == "both":
+        pushed = await push_pending_events(owner)
+        pulled = await sync_caldav(owner)
+        return {"push": pushed, "pull": pulled}
+    return {
+        "calendars": 0,
+        "events": 0,
+        "deleted": 0,
+        "errors": [f"Unsupported CalDAV sync direction: {direction}"],
+    }

src/caldav_writeback.py

@@ -89,6 +89,23 @@ def find_remote_calendar(calendars, local_cal_id: str, owner: str = "", account_
     return None
 
 
+def _resource_href(obj) -> str:
+    try:
+        return str(getattr(obj, "url", "") or "")
+    except Exception:
+        return ""
+
+
+def _resource_etag(obj) -> str:
+    try:
+        etag = getattr(obj, "etag", None)
+        if callable(etag):
+            etag = etag()
+        return str(etag or "")
+    except Exception:
+        return ""
+
+
 def push_event(calendars, local_cal_id: str, ev: dict, *, delete: bool = False,
                owner: str = "", account_id: str = "") -> dict:
     """Create/update (or delete) ``ev`` on the matching remote calendar.
@@ -105,6 +122,7 @@ def push_event(calendars, local_cal_id: str, ev: dict, *, delete: bool = False,
     remote = find_remote_calendar(calendars, local_cal_id, owner=owner, account_id=account_id)
     if remote is None:
         return {"ok": False, "error": "remote calendar not found"}
+    remote_url = str(getattr(remote, "url", "") or "")
 
     try:
         existing = remote.event_by_uid(uid)
@@ -113,17 +131,34 @@ def push_event(calendars, local_cal_id: str, ev: dict, *, delete: bool = False,
 
     if delete:
         if existing is None:
-            return {"ok": True, "note": "already absent on remote"}
+            return {"ok": True, "note": "already absent on remote", "calendar_url": remote_url}
         existing.delete()
-        return {"ok": True}
+        return {
+            "ok": True,
+            "calendar_url": remote_url,
+            "remote_href": _resource_href(existing),
+            "remote_etag": _resource_etag(existing),
+        }
 
     ical = build_event_ical(ev)
     if existing is not None:
         existing.data = ical
         existing.save()
-        return {"ok": True, "updated": True}
-    remote.save_event(ical)
-    return {"ok": True, "created": True}
+        return {
+            "ok": True,
+            "updated": True,
+            "calendar_url": remote_url,
+            "remote_href": _resource_href(existing),
+            "remote_etag": _resource_etag(existing),
+        }
+    created = remote.save_event(ical)
+    return {
+        "ok": True,
+        "created": True,
+        "calendar_url": remote_url,
+        "remote_href": _resource_href(created),
+        "remote_etag": _resource_etag(created),
+    }
 
 
 def _discover_calendars(client):
@@ -154,6 +189,54 @@ def _writeback_blocking(local_cal_id, ev, delete, url, username, password,
                       owner=owner, account_id=account_id)
 
 
+def _persist_writeback_result(owner: str, calendar_id: str, uid: str, result: dict, *, delete: bool) -> None:
+    from core.database import CalendarCal, CalendarDeletedEvent, CalendarEvent, SessionLocal
+
+    if not uid or not isinstance(result, dict):
+        return
+
+    db = SessionLocal()
+    try:
+        calendar = db.query(CalendarCal).filter(
+            CalendarCal.id == calendar_id,
+            CalendarCal.owner == owner,
+        ).first()
+        if calendar and result.get("calendar_url"):
+            calendar.caldav_base_url = result.get("calendar_url")
+
+        if delete:
+            tombstone = db.query(CalendarDeletedEvent).filter(
+                CalendarDeletedEvent.uid == uid,
+                CalendarDeletedEvent.owner == owner,
+            ).first()
+            if result.get("ok"):
+                if tombstone:
+                    db.delete(tombstone)
+            elif tombstone:
+                tombstone.last_error = str(result.get("error") or result)[:500]
+            db.commit()
+            return
+
+        event = (
+            db.query(CalendarEvent)
+            .join(CalendarCal)
+            .filter(CalendarEvent.uid == uid, CalendarCal.owner == owner)
+            .first()
+        )
+        if event and result.get("ok"):
+            if result.get("remote_href"):
+                event.remote_href = result.get("remote_href")
+            if result.get("remote_etag"):
+                event.remote_etag = result.get("remote_etag")
+            event.caldav_sync_pending = None
+        db.commit()
+    except Exception:
+        db.rollback()
+        logger.exception("CalDAV write-back metadata persistence failed")
+    finally:
+        db.close()
+
+
 async def writeback_event(owner: str, calendar_source: str, calendar_id: str,
                           ev: dict, *, delete: bool = False) -> dict:
     """Best-effort push of a local change to the remote CalDAV server.
@@ -204,9 +287,12 @@ async def writeback_event(owner: str, calendar_source: str, calendar_id: str,
         result = await asyncio.to_thread(
             _writeback_blocking, calendar_id, ev, delete, url, user, pw, owner, acc_id
         )
+        _persist_writeback_result(owner, calendar_id, (ev or {}).get("uid", ""), result, delete=delete)
         if not result.get("ok"):
             logger.warning("CalDAV write-back did not apply: %s", result.get("error") or result)
         return result
     except Exception as e:
         logger.exception("CalDAV write-back raised")
-        return {"ok": False, "error": str(e)[:200]}
+        result = {"ok": False, "error": str(e)[:200]}
+        _persist_writeback_result(owner, calendar_id, (ev or {}).get("uid", ""), result, delete=delete)
+        return result

src/tool_implementations.py

@@ -1445,7 +1445,15 @@ async def do_manage_calendar(content: str, owner: Optional[str] = None) -> Dict:
     """Handle manage_calendar tool calls: list/create/update/delete calendar events (local SQLite)."""
     from datetime import datetime, timedelta
     from core.database import SessionLocal, CalendarCal, CalendarEvent, Note
-    from routes.calendar_routes import _ensure_default_calendar, _parse_dt, _parse_dt_pair, parse_due_for_user, _resolve_base_uid
+    from routes.calendar_routes import (
+        _ensure_default_calendar,
+        _parse_dt,
+        _parse_dt_pair,
+        parse_due_for_user,
+        _resolve_base_uid,
+        _push_caldav_event_after_commit,
+        _record_caldav_delete_tombstone,
+    )
     import uuid as _uuid
 
     try:
@@ -1825,6 +1833,7 @@ async def do_manage_calendar(content: str, owner: Optional[str] = None) -> Dict:
                 rrule=args.get("rrule", "") or "",
                 event_type=event_type,
                 importance=importance,
+                caldav_sync_pending="create" if cal.source == "caldav" else None,
             )
             db.add(ev)
             reminder_note_id = None
@@ -1839,6 +1848,8 @@ async def do_manage_calendar(content: str, owner: Optional[str] = None) -> Dict:
                     dtstart_is_utc and not all_day,
                 )
             db.commit()
+            if cal.source == "caldav":
+                await _push_caldav_event_after_commit(owner, uid, "create")
             tag_blurb = f" [{event_type}]" if event_type else ""
             if minutes_before is None:
                 reminder_blurb = ""
@@ -1896,7 +1907,12 @@ async def do_manage_calendar(content: str, owner: Optional[str] = None) -> Dict:
                 ev.event_type = _tag or None
             if args.get("importance") is not None:
                 ev.importance = args["importance"]
+            is_caldav = ev.calendar and ev.calendar.source == "caldav"
+            if is_caldav:
+                ev.caldav_sync_pending = "update"
             db.commit()
+            if is_caldav:
+                await _push_caldav_event_after_commit(owner, base_uid, "update")
             return {"response": f"Updated event {uid}", "exit_code": 0}
 
         elif action == "delete_event":
@@ -1910,8 +1926,13 @@ async def do_manage_calendar(content: str, owner: Optional[str] = None) -> Dict:
             ev = _event_query().filter(CalendarEvent.uid == base_uid).first()
             if not ev:
                 return {"error": f"Event {uid} not found", "exit_code": 1}
+            is_caldav = ev.calendar and ev.calendar.source == "caldav" and ev.remote_href
+            if is_caldav:
+                _record_caldav_delete_tombstone(db, ev, owner)
             db.delete(ev)
             db.commit()
+            if is_caldav:
+                await _push_caldav_event_after_commit(owner, base_uid, "delete")
             return {"response": f"Deleted event {uid}", "exit_code": 0}
 
         else:

tests/test_caldav_bidirectional_sync.py

@@ -0,0 +1,169 @@
+"""Regression coverage for bidirectional CalDAV sync plumbing.
+
+These tests avoid a live CalDAV server. They pin the local invariants that keep
+Odysseus-created CalDAV events from being pruned before they can be pushed.
+"""
+
+from datetime import datetime
+import importlib.util
+from pathlib import Path
+import sys
+
+from src.caldav_writeback import build_event_ical
+
+
+def test_event_to_ical_serializes_core_fields_and_rrule():
+    ical = build_event_ical({
+        "uid": "evt-123",
+        "summary": "Planning",
+        "description": "Bring notes",
+        "location": "HQ",
+        "dtstart": datetime(2026, 6, 5, 9, 0),
+        "dtend": datetime(2026, 6, 5, 10, 0),
+        "all_day": False,
+        "is_utc": False,
+        "rrule": "FREQ=WEEKLY;COUNT=2",
+    })
+
+    assert "UID:evt-123" in ical
+    assert "SUMMARY:Planning" in ical
+    assert "DESCRIPTION:Bring notes" in ical
+    assert "LOCATION:HQ" in ical
+    assert "RRULE:FREQ=WEEKLY;COUNT=2" in ical
+
+
+def test_caldav_pull_prune_skips_unsynced_or_pending_local_rows():
+    source = Path("src/caldav_sync.py").read_text()
+
+    assert 'existing.caldav_sync_pending in {"create", "update"}' in source
+    assert "CalendarEvent.remote_href.isnot(None)" in source
+    assert "CalendarEvent.caldav_sync_pending.is_(None)" in source
+
+
+def test_http_calendar_writes_mark_pending_and_push_after_commit():
+    source = Path("routes/calendar_routes.py").read_text()
+
+    assert 'caldav_sync_pending="create" if cal.source == "caldav" else None' in source
+    assert 'ev.caldav_sync_pending = "update"' in source
+    assert 'await _push_caldav_event_after_commit(owner, uid, "create")' in source
+    assert 'await _push_caldav_event_after_commit(owner, base_uid, "update")' in source
+    assert 'await _push_caldav_event_after_commit(owner, base_uid, "delete")' in source
+    assert "_record_caldav_delete_tombstone(db, ev, owner)" in source
+    assert 'not result.get("ok")' in source
+
+
+def test_agent_calendar_writes_share_caldav_push_path():
+    source = Path("src/tool_implementations.py").read_text()
+
+    assert "_push_caldav_event_after_commit" in source
+    assert 'caldav_sync_pending="create" if cal.source == "caldav" else None' in source
+    assert 'ev.caldav_sync_pending = "update"' in source
+    assert 'await _push_caldav_event_after_commit(owner, uid, "create")' in source
+    assert 'await _push_caldav_event_after_commit(owner, base_uid, "update")' in source
+    assert 'await _push_caldav_event_after_commit(owner, base_uid, "delete")' in source
+    assert "_record_caldav_delete_tombstone(db, ev, owner)" in source
+
+
+def test_database_declares_and_migrates_caldav_remote_metadata():
+    source = Path("core/database.py").read_text()
+
+    for needle in [
+        "class CalendarDeletedEvent",
+        "remote_href = Column(String, nullable=True)",
+        "remote_etag = Column(String, nullable=True)",
+        "caldav_sync_pending = Column(String, nullable=True)",
+        "caldav_base_url = Column(String, nullable=True)",
+        "ALTER TABLE calendar_events ADD COLUMN remote_href TEXT",
+        "ALTER TABLE calendar_events ADD COLUMN remote_etag TEXT",
+        "ALTER TABLE calendar_events ADD COLUMN caldav_sync_pending TEXT",
+        "ALTER TABLE calendars ADD COLUMN caldav_base_url TEXT",
+        "_migrate_add_caldav_sync_columns()",
+    ]:
+        assert needle in source
+
+
+def test_failed_remote_delete_leaves_tombstone_and_later_retry_cleans_up(tmp_path, monkeypatch):
+    import src.caldav_writeback as writeback
+
+    monkeypatch.setenv("DATABASE_URL", f"sqlite:///{tmp_path / 'calendar.db'}")
+    spec = importlib.util.spec_from_file_location("core.database", Path("core/database.py"))
+    dbmod = importlib.util.module_from_spec(spec)
+    monkeypatch.setitem(sys.modules, "core.database", dbmod)
+    spec.loader.exec_module(dbmod)
+
+    CalendarCal = dbmod.CalendarCal
+    CalendarDeletedEvent = dbmod.CalendarDeletedEvent
+    CalendarEvent = dbmod.CalendarEvent
+    TestingSessionLocal = dbmod.SessionLocal
+
+    session = TestingSessionLocal()
+    try:
+        cal = CalendarCal(
+            id="caldav-test",
+            owner="alice",
+            name="Remote",
+            source="caldav",
+            caldav_base_url="https://caldav.example/calendars/alice/main/",
+        )
+        ev = CalendarEvent(
+            uid="evt-delete",
+            calendar_id=cal.id,
+            summary="Delete me",
+            dtstart=datetime(2026, 6, 5, 9, 0),
+            dtend=datetime(2026, 6, 5, 10, 0),
+            remote_href="https://caldav.example/calendars/alice/main/evt-delete.ics",
+        )
+        session.add(cal)
+        session.add(ev)
+        session.commit()
+
+        tombstone = CalendarDeletedEvent(
+            uid=ev.uid,
+            owner="alice",
+            calendar_id=ev.calendar_id,
+            remote_href=ev.remote_href,
+            remote_etag=ev.remote_etag,
+            caldav_base_url=cal.caldav_base_url,
+            summary=ev.summary,
+        )
+        session.add(tombstone)
+        session.delete(ev)
+        session.commit()
+
+        assert session.query(CalendarEvent).filter_by(uid="evt-delete").first() is None
+        tombstone = session.query(CalendarDeletedEvent).filter_by(uid="evt-delete").first()
+        assert tombstone is not None
+        assert tombstone.remote_href.endswith("evt-delete.ics")
+    finally:
+        session.close()
+
+    writeback._persist_writeback_result(
+        "alice",
+        "caldav-test",
+        "evt-delete",
+        {"ok": False, "error": "temporary remote delete failure"},
+        delete=True,
+    )
+
+    session = TestingSessionLocal()
+    try:
+        tombstone = session.query(CalendarDeletedEvent).filter_by(uid="evt-delete").first()
+        assert tombstone is not None
+        assert "temporary remote delete failure" in tombstone.last_error
+    finally:
+        session.close()
+
+    writeback._persist_writeback_result(
+        "alice",
+        "caldav-test",
+        "evt-delete",
+        {"ok": True},
+        delete=True,
+    )
+
+    session = TestingSessionLocal()
+    try:
+        assert session.query(CalendarDeletedEvent).filter_by(uid="evt-delete").first() is None
+        assert session.query(CalendarEvent).filter_by(uid="evt-delete").first() is None
+    finally:
+        session.close()

tests/test_caldav_writeback.py

@@ -22,7 +22,9 @@ CAL_ID = _stable_cal_id(REMOTE_URL)
 
 
 class FakeEvent:
-    def __init__(self):
+    def __init__(self, url="https://p69-caldav.icloud.com/123/calendars/home/evt-1.ics"):
+        self.url = url
+        self.etag = '"abc123"'
         self.data = "OLD"
         self.saved = False
         self.deleted = False
@@ -39,6 +41,7 @@ class FakeCalendar:
         self.url = url
         self._existing = existing
         self.saved_ical = None
+        self.created = FakeEvent(str(url).rstrip("/") + "/created.ics")
 
     def event_by_uid(self, uid):
         if self._existing is None:
@@ -47,6 +50,7 @@ class FakeCalendar:
 
     def save_event(self, ical):
         self.saved_ical = ical
+        return self.created
 
 
 def _ev(**over):
@@ -91,6 +95,8 @@ def test_push_create_calls_save_event():
     res = push_event([cal], CAL_ID, _ev(), delete=False)
     assert res["ok"] and res.get("created")
     assert cal.saved_ical and "UID:evt-1" in cal.saved_ical
+    assert res["calendar_url"] == REMOTE_URL
+    assert res["remote_href"].endswith("/created.ics")
 
 
 def test_push_update_overwrites_existing():
@@ -100,6 +106,8 @@ def test_push_update_overwrites_existing():
     assert res["ok"] and res.get("updated")
     assert existing.saved and "SUMMARY:Moved" in existing.data
     assert cal.saved_ical is None  # used update path, not create
+    assert res["remote_href"].endswith("evt-1.ics")
+    assert res["remote_etag"] == '"abc123"'
 
 
 def test_push_delete_removes_existing():

tests/test_caldav_writeback_route.py

@@ -20,7 +20,7 @@ from sqlalchemy.pool import NullPool
 
 import core.database as cdb
 import routes.calendar_routes as croutes
-import src.caldav_writeback as wb
+import src.caldav_sync as csync
 from core.database import CalendarCal
 from routes.calendar_routes import EventCreate
 
@@ -39,11 +39,16 @@ croutes.SessionLocal = _TS
 def calls(monkeypatch):
     recorded = []
 
-    async def _fake_writeback(owner, source, cal_id, ev, *, delete=False):
-        recorded.append({"source": source, "cal_id": cal_id, "uid": ev.get("uid"), "delete": delete})
+    async def _fake_create(owner, uid):
+        recorded.append({"uid": uid, "delete": False, "action": "create"})
         return {"ok": True}
 
-    monkeypatch.setattr(wb, "writeback_event", _fake_writeback)
+    async def _fake_delete(owner, uid):
+        recorded.append({"uid": uid, "delete": True, "action": "delete"})
+        return {"ok": True}
+
+    monkeypatch.setattr(csync, "push_event_create", _fake_create)
+    monkeypatch.setattr(csync, "push_event_delete", _fake_delete)
     return recorded
 
 
@@ -77,7 +82,6 @@ async def test_create_on_caldav_calendar_pushes_to_remote(calls):
         summary="Dentist", dtstart="2026-06-10T14:00:00Z", calendar_href=cal_id))
     assert res["ok"] is True
     assert len(calls) == 1
-    assert calls[0]["source"] == "caldav" and calls[0]["cal_id"] == cal_id
     assert calls[0]["delete"] is False
 
 

tests/test_calendar_owner_scope.py

@@ -151,6 +151,7 @@ def _install_calendar_db_stub(monkeypatch):
     db = types.ModuleType("core.database")
     db.SessionLocal = MagicMock()
     db.CalendarCal = _CalendarCal
+    db.CalendarDeletedEvent = MagicMock()
     db.CalendarEvent = _CalendarEvent
     for name in [
         "Base",

tests/test_null_owner_gates.py

@@ -28,7 +28,7 @@ from unittest.mock import MagicMock
 def _null_owner_stubs(monkeypatch):
     for _stub, _attrs in (
         ("core.database", (
-            "Base", "SessionLocal", "CalendarCal", "CalendarEvent",
+            "Base", "SessionLocal", "CalendarCal", "CalendarDeletedEvent", "CalendarEvent",
             "Document", "DocumentVersion", "Session", "ChatMessage",
             "GalleryImage", "GalleryAlbum", "Note", "ScheduledTask",
             "TaskRun", "ModelEndpoint", "Webhook",