fix(sessions): keep fresh chats during auto tidy (#1871)

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

routes/session_routes.py

@@ -10,8 +10,9 @@ import logging
 from core.session_manager import SessionManager
 from core.models import ChatMessage
 from src.request_models import SessionResponse
-from core.database import Session as DbSession, SessionLocal, Document, GalleryImage
+from core.database import Session as DbSession, SessionLocal, Document, GalleryImage, utcnow_naive
 from src.auth_helpers import get_current_user, effective_user, _auth_disabled
+from src.session_actions import is_session_recently_active
 
 
 def _sanitize_export_filename(name: str) -> str:
@@ -1028,6 +1029,7 @@ def setup_session_routes(session_manager: SessionManager, config: dict, webhook_
                 db.query(DbMsg.session_id, _sa_func.count(DbMsg.id))
                 .filter(DbMsg.role == "assistant").group_by(DbMsg.session_id).all()
             )
+            cleanup_now = utcnow_naive()
             for row in rows:
                 # Never delete important sessions
                 if getattr(row, 'is_important', False):
@@ -1040,6 +1042,8 @@ def setup_session_routes(session_manager: SessionManager, config: dict, webhook_
                     if hasattr(session_manager, 'delete_session'):
                         session_manager.delete_session(row.id)
                     continue
+                if is_session_recently_active(row, now=cleanup_now):
+                    continue
                 msg_count = _counts.get(row.id, 0)
                 should_delete = False
                 if msg_count == 0:

src/session_actions.py

@@ -8,7 +8,7 @@ and the task scheduler / builtin actions system.
 import json
 import logging
 import re
-from datetime import datetime, timedelta
+from datetime import datetime, timedelta, timezone
 
 logger = logging.getLogger(__name__)
 
@@ -23,6 +23,34 @@ _THROWAWAY_NAMES = {
 }
 _THROWAWAY_MAX_MESSAGES = 4
 _FRESH_EMPTY_SESSION_GRACE = timedelta(minutes=10)
+_FRESH_SESSION_GRACE = _FRESH_EMPTY_SESSION_GRACE
+
+
+def _utcnow_naive() -> datetime:
+    """Return naive UTC for existing session DateTime columns."""
+    return datetime.now(timezone.utc).replace(tzinfo=None)
+
+
+def _as_naive_utc(value):
+    if value is None:
+        return None
+    if getattr(value, "tzinfo", None) is not None:
+        return value.astimezone(timezone.utc).replace(tzinfo=None)
+    return value
+
+
+def is_session_recently_active(row, now=None, grace=_FRESH_SESSION_GRACE) -> bool:
+    """Return True while a new or active session is too fresh to auto-delete."""
+    now = _as_naive_utc(now) or _utcnow_naive()
+    for attr in ("last_message_at", "last_accessed", "updated_at", "created_at"):
+        value = _as_naive_utc(getattr(row, attr, None))
+        if not value:
+            continue
+        if value >= now:
+            return True
+        if now - value <= grace:
+            return True
+    return False
 
 
 async def run_auto_sort(owner: str, skip_llm: bool = False, delete_throwaway: bool = True) -> str:
@@ -52,15 +80,18 @@ async def run_auto_sort(owner: str, skip_llm: bool = False, delete_throwaway: bo
             *([DbSession.owner == owner] if owner else []),
         ).all()
 
+        cleanup_now = _utcnow_naive()
         for row in rows:
             if getattr(row, 'is_important', False):
                 continue
-            created_at = row.created_at or row.updated_at or datetime.utcnow()
-            is_fresh = (datetime.utcnow() - created_at) < _FRESH_EMPTY_SESSION_GRACE
+            created_at = _as_naive_utc(row.created_at or row.updated_at) or _utcnow_naive()
+            is_fresh = (_utcnow_naive() - created_at) < _FRESH_EMPTY_SESSION_GRACE
             if (row.name or "").strip() == "Incognito":
                 deleted_throwaway += 1
                 db.delete(row)
                 continue
+            if is_session_recently_active(row, now=cleanup_now):
+                continue
 
             msg_count = db.query(DbMsg.id).filter(
                 DbMsg.session_id == row.id
@@ -208,7 +239,7 @@ async def run_auto_sort(owner: str, skip_llm: bool = False, delete_throwaway: bo
                     db_sess = db.query(DbSession).filter(DbSession.id == full_id).first()
                     if db_sess:
                         db_sess.folder = folder_name
-                        db_sess.updated_at = datetime.utcnow()
+                        db_sess.updated_at = _utcnow_naive()
                         updated += 1
         db.commit()
 

tests/test_session_actions_cleanup.py

@@ -0,0 +1,166 @@
+"""Regression coverage for auto-sort session cleanup.
+
+Issue #1851 reported fresh chats being deleted immediately after their first
+turn, leaving the browser pointed at a session id that no longer exists.
+"""
+
+import asyncio
+from datetime import timedelta
+import sys
+import tempfile
+import uuid
+
+import pytest
+
+sqlalchemy = pytest.importorskip("sqlalchemy")
+if type(sqlalchemy).__name__ == "MagicMock":
+    pytest.skip("sqlalchemy is stubbed in this environment", allow_module_level=True)
+
+from sqlalchemy import create_engine
+from sqlalchemy.orm import sessionmaker
+from sqlalchemy.pool import NullPool
+
+import core.database as cdb
+from core.database import ChatMessage as DbMessage, Session as DbSession, utcnow_naive
+import src.session_actions as session_actions
+
+
+def _make_session_factory():
+    tmp = tempfile.NamedTemporaryFile(suffix=".db", delete=False)
+    tmp.close()
+    engine = create_engine(
+        f"sqlite:///{tmp.name}",
+        connect_args={"check_same_thread": False},
+        poolclass=NullPool,
+    )
+    DbSession.metadata.create_all(bind=engine)
+    return sessionmaker(bind=engine, autoflush=False, autocommit=False)
+
+
+def _install_session_factory(monkeypatch, session_factory):
+    monkeypatch.setitem(sys.modules, "core.database", cdb)
+    core_pkg = sys.modules.get("core")
+    if core_pkg is not None:
+        monkeypatch.setattr(core_pkg, "database", cdb, raising=False)
+    monkeypatch.setattr(cdb, "SessionLocal", session_factory)
+
+
+def _add_message(db, sid, role, content, timestamp):
+    db.add(
+        DbMessage(
+            id="m-" + uuid.uuid4().hex,
+            session_id=sid,
+            role=role,
+            content=content,
+            timestamp=timestamp,
+        )
+    )
+
+
+def test_auto_sort_keeps_fresh_chat_with_completed_first_turn(monkeypatch):
+    session_factory = _make_session_factory()
+    _install_session_factory(monkeypatch, session_factory)
+
+    sid = "s-" + uuid.uuid4().hex
+    db = session_factory()
+    try:
+        db.add(
+            DbSession(
+                id=sid,
+                owner="alice",
+                name="Quick question",
+                endpoint_url="",
+                model="",
+                archived=False,
+                message_count=2,
+                last_message_at=utcnow_naive(),
+            )
+        )
+        _add_message(db, sid, "user", "hi", utcnow_naive())
+        _add_message(db, sid, "assistant", "Hello! How can I help?", utcnow_naive())
+        db.commit()
+    finally:
+        db.close()
+
+    result = asyncio.run(session_actions.run_auto_sort("alice", skip_llm=True))
+
+    db = session_factory()
+    try:
+        assert db.query(DbSession).filter(DbSession.id == sid).first() is not None
+        assert db.query(DbMessage).filter(DbMessage.session_id == sid).count() == 2
+        assert "Cleaned 0 sessions" in result
+    finally:
+        db.close()
+
+
+def test_auto_sort_keeps_fresh_session_while_first_response_is_pending(monkeypatch):
+    session_factory = _make_session_factory()
+    _install_session_factory(monkeypatch, session_factory)
+
+    sid = "s-" + uuid.uuid4().hex
+    db = session_factory()
+    try:
+        db.add(
+            DbSession(
+                id=sid,
+                owner="alice",
+                name="New chat",
+                endpoint_url="",
+                model="",
+                archived=False,
+                message_count=1,
+                last_message_at=utcnow_naive(),
+            )
+        )
+        _add_message(db, sid, "user", "Tell me a quick joke", utcnow_naive())
+        db.commit()
+    finally:
+        db.close()
+
+    result = asyncio.run(session_actions.run_auto_sort("alice", skip_llm=True))
+
+    db = session_factory()
+    try:
+        assert db.query(DbSession).filter(DbSession.id == sid).first() is not None
+        assert db.query(DbMessage).filter(DbMessage.session_id == sid).count() == 1
+        assert "Cleaned 0 sessions" in result
+    finally:
+        db.close()
+
+
+def test_auto_sort_still_deletes_old_throwaway_sessions(monkeypatch):
+    session_factory = _make_session_factory()
+    _install_session_factory(monkeypatch, session_factory)
+
+    old_time = utcnow_naive() - timedelta(hours=2)
+    sid = "s-" + uuid.uuid4().hex
+    db = session_factory()
+    try:
+        db.add(
+            DbSession(
+                id=sid,
+                owner="alice",
+                name="New chat",
+                endpoint_url="",
+                model="",
+                archived=False,
+                message_count=1,
+                created_at=old_time,
+                updated_at=old_time,
+                last_accessed=old_time,
+                last_message_at=old_time,
+            )
+        )
+        _add_message(db, sid, "user", "hi", old_time)
+        db.commit()
+    finally:
+        db.close()
+
+    result = asyncio.run(session_actions.run_auto_sort("alice", skip_llm=True))
+
+    db = session_factory()
+    try:
+        assert db.query(DbSession).filter(DbSession.id == sid).first() is None
+        assert "Cleaned 1 sessions" in result
+    finally:
+        db.close()