fix(chats): preserve saved conversations during tidy

routes/session_routes.py

@@ -1305,7 +1305,7 @@ def setup_session_routes(
     def auto_sort_sessions(request: Request, skip_llm: bool = False):
         """Use AI to categorize all sessions into folders.
 
-        Phase 1 deletes empty/throwaway sessions and Phase 2 asks the LLM
+        Phase 1 deletes empty/Incognito sessions and Phase 2 asks the LLM
         to assign folders. When `skip_llm=true` the endpoint returns
         after Phase 1 — used by the "Tidy (no AI)" UI affordance so
         users can clean junk without spending tokens.
@@ -1315,21 +1315,11 @@ def setup_session_routes(
         single_user_mode = not user and _auth_disabled()
         user_sessions = session_manager.get_sessions_for_user(user)
 
-        # Delete empty and throwaway sessions before sorting
+        # Saved conversations are never disposable based on their title or prompt.
         from core.database import ChatMessage as DbMsg
         db = SessionLocal()
         deleted_empty = 0
         deleted_throwaway = 0
-        # Names that indicate a throwaway/test session (case-insensitive exact or prefix match)
-        _THROWAWAY_NAMES = {
-            "test", "testing", "asdf", "asd", "hello", "hi", "hey",
-            "yo", "sup", "hola", "hii", "hiii", "heyo",
-            "foo", "bar", "baz", "tmp", "temp", "scratch", "untitled",
-            "new chat", "delete", "remove", "junk", "trash", "xxx",
-            "abc", "qwerty", "blah", "stuff", "whatever", "idk",
-            "ok", "lol", "bruh", "hmm", "hm", "meh",
-        }
-        _THROWAWAY_MAX_MESSAGES = 4  # only delete if <= this many messages
         try:
             rows_q = db.query(DbSession).filter(DbSession.archived == False)
             if user:
@@ -1338,15 +1328,11 @@ def setup_session_routes(
                 rows_q = rows_q.filter(DbSession.owner == user)
             rows = rows_q.limit(2000).all()
             folder_map = {r.id: r.folder for r in rows}
-            # Precompute per-session message counts in TWO aggregate queries
+            # Precompute per-session message counts in one aggregate query
             # instead of 1–3 queries PER session — with many chats the per-row
             # loop was doing thousands of round-trips and blowing the timeout.
             from sqlalchemy import func as _sa_func
             _counts = dict(db.query(DbMsg.session_id, _sa_func.count(DbMsg.id)).group_by(DbMsg.session_id).all())
-            _asst_counts = dict(
-                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
@@ -1356,9 +1342,10 @@ def setup_session_routes(
                 if (row.name or "").strip() == "Incognito":
                     should_delete = True
                     deleted_throwaway += 1
-                    db.delete(row)
                     if hasattr(session_manager, 'delete_session'):
                         session_manager.delete_session(row.id)
+                    else:
+                        db.delete(row)
                     continue
                 if is_session_recently_active(row, now=cleanup_now):
                     continue
@@ -1367,31 +1354,11 @@ def setup_session_routes(
                 if msg_count == 0:
                     should_delete = True
                     deleted_empty += 1
-                elif msg_count <= _THROWAWAY_MAX_MESSAGES:
-                    name = (row.name or "").strip().lower()
-                    # Check first user message content (AI renames sessions, so
-                    # "hi" becomes "Casual Greeting Exchange" — name alone won't match)
-                    first_msg = db.query(DbMsg.content).filter(
-                        DbMsg.session_id == row.id, DbMsg.role == "user"
-                    ).order_by(DbMsg.timestamp).first()
-                    first_text = (first_msg[0] or "").strip().lower() if first_msg else ""
-                    # Count assistant messages — if user sent something but AI never replied, it's dead
-                    assistant_count = _asst_counts.get(row.id, 0)
-                    if name in _THROWAWAY_NAMES or name.startswith("chat:") or first_text in _THROWAWAY_NAMES:
-                        should_delete = True
-                        deleted_throwaway += 1
-                    # Single user message with no AI response = dead session
-                    elif msg_count == 1 and assistant_count == 0:
-                        should_delete = True
-                        deleted_throwaway += 1
-                    # Short phrase (1-3 words) with no real AI conversation (<=2 msgs)
-                    elif msg_count <= 2 and first_text and len(first_text.split()) <= 3 and len(first_text) <= 40:
-                        should_delete = True
-                        deleted_throwaway += 1
                 if should_delete:
-                    db.delete(row)
                     if hasattr(session_manager, 'delete_session'):
                         session_manager.delete_session(row.id)
+                    else:
+                        db.delete(row)
             if deleted_empty or deleted_throwaway:
                 db.commit()
                 logger.info(f"Auto-sort: deleted {deleted_empty} empty + {deleted_throwaway} throwaway sessions")

src/session_actions.py

@@ -12,16 +12,6 @@ from datetime import datetime, timedelta, timezone
 
 logger = logging.getLogger(__name__)
 
-# Names that indicate a throwaway/test session
-_THROWAWAY_NAMES = {
-    "test", "testing", "asdf", "asd", "hello", "hi", "hey",
-    "yo", "sup", "hola", "hii", "hiii", "heyo",
-    "foo", "bar", "baz", "tmp", "temp", "scratch", "untitled",
-    "new chat", "delete", "remove", "junk", "trash", "xxx",
-    "abc", "qwerty", "blah", "stuff", "whatever", "idk",
-    "ok", "lol", "bruh", "hmm", "hm", "meh",
-}
-_THROWAWAY_MAX_MESSAGES = 4
 _FRESH_EMPTY_SESSION_GRACE = timedelta(minutes=10)
 _FRESH_SESSION_GRACE = _FRESH_EMPTY_SESSION_GRACE
 
@@ -54,14 +44,15 @@ def is_session_recently_active(row, now=None, grace=_FRESH_SESSION_GRACE) -> boo
 
 
 async def run_auto_sort(owner: str, skip_llm: bool = False, delete_throwaway: bool = True) -> str:
-    """Run session cleanup + (optional) AI folder sort for the given owner.
+    """Remove empty/Incognito sessions and optionally organize saved chats.
 
     Args:
         owner: user whose sessions to process
-        skip_llm: when True, do only Phase 1 (delete empty/throwaway sessions);
+        skip_llm: when True, do only Phase 1 (delete empty/Incognito sessions);
             skip Phase 2 (AI folder assignment). Used by the built-in daily
             background sweep so it never burns LLM tokens.
-        delete_throwaway: when False, only empty/incognito sessions are deleted.
+        delete_throwaway: retained for caller compatibility. Ordinary sessions
+            with saved messages are always preserved, regardless of this flag.
 
     Returns a human-readable summary of what was done.
     """
@@ -71,7 +62,7 @@ async def run_auto_sort(owner: str, skip_llm: bool = False, delete_throwaway: bo
 
     db = SessionLocal()
     try:
-        # ── Phase 1: Delete empty/throwaway sessions ──
+        # ── Phase 1: Delete only empty and explicitly Incognito sessions ──
         deleted_empty = 0
         deleted_throwaway = 0
 
@@ -93,47 +84,13 @@ async def run_auto_sort(owner: str, skip_llm: bool = False, delete_throwaway: bo
             if is_session_recently_active(row, now=cleanup_now):
                 continue
 
-            msg_count = db.query(DbMsg.id).filter(
+            has_messages = db.query(DbMsg.id).filter(
                 DbMsg.session_id == row.id
-            ).limit(_THROWAWAY_MAX_MESSAGES + 1).count()
+            ).first() is not None
-            should_delete = False
+            if not has_messages:
-
-            if msg_count == 0:
                 if is_fresh:
                     continue
-                should_delete = True
                 deleted_empty += 1
-            elif delete_throwaway and msg_count <= _THROWAWAY_MAX_MESSAGES:
-                name = (row.name or "").strip().lower()
-                first_msg = db.query(DbMsg.content).filter(
-                    DbMsg.session_id == row.id, DbMsg.role == "user"
-                ).order_by(DbMsg.timestamp).first()
-                first_text = (first_msg[0] or "").strip().lower() if first_msg else ""
-                assistant_count = db.query(DbMsg.id).filter(
-                    DbMsg.session_id == row.id, DbMsg.role == "assistant"
-                ).limit(1).count()
-
-                if name in _THROWAWAY_NAMES or name.startswith("chat:") or first_text in _THROWAWAY_NAMES:
-                    should_delete = True
-                    deleted_throwaway += 1
-                elif msg_count == 1 and assistant_count == 0:
-                    should_delete = True
-                    deleted_throwaway += 1
-                elif msg_count <= 4 and first_text and len(first_text.split()) <= 8 and len(first_text) <= 80:
-                    # Short trivial chats — e.g. "write hi to a friend" → "Hi!"
-                    should_delete = True
-                    deleted_throwaway += 1
-                else:
-                    # Aggressive: total message text under 250 chars combined = trivial
-                    msg_rows = db.query(DbMsg.content).filter(
-                        DbMsg.session_id == row.id
-                    ).all()
-                    total_chars = sum(len(m[0] or "") for m in msg_rows)
-                    if total_chars <= 250:
-                        should_delete = True
-                        deleted_throwaway += 1
-
-            if should_delete:
                 db.delete(row)
 
         if deleted_empty or deleted_throwaway:

tests/test_chat_tidy_content_preservation.py

@@ -0,0 +1,148 @@
+"""Both chat tidy entry points retain saved conversations and still remove empties."""
+import asyncio
+from datetime import datetime, timedelta, timezone
+
+import pytest
+from fastapi import APIRouter, FastAPI
+from fastapi.testclient import TestClient
+from sqlalchemy import create_engine
+from sqlalchemy.orm import sessionmaker
+
+import core.database as database
+import core.session_manager as manager_module
+import routes.session_routes as routes
+import src.session_actions as actions
+
+
+@pytest.fixture
+def tidy_api(tmp_path, monkeypatch):
+    engine = create_engine(
+        f"sqlite:///{(tmp_path / 'tidy.db').as_posix()}",
+        connect_args={"check_same_thread": False},
+    )
+    database.Base.metadata.create_all(engine)
+    factory = sessionmaker(bind=engine, autoflush=False)
+    monkeypatch.setattr(database, "SessionLocal", factory)
+    monkeypatch.setattr(manager_module, "SessionLocal", factory)
+    monkeypatch.setattr(routes, "SessionLocal", factory)
+    monkeypatch.setattr(routes, "router", APIRouter(prefix="/api"))
+    monkeypatch.setattr(routes, "effective_user", lambda request: "alice")
+    manager = manager_module.SessionManager.__new__(manager_module.SessionManager)
+    manager.sessions = {}
+    manager.upload_handler = None
+    monkeypatch.setattr(manager, "get_sessions_for_user", lambda owner: {})
+    app = FastAPI()
+    app.include_router(routes.setup_session_routes(manager, {}))
+    with TestClient(app) as client:
+        yield client, factory, manager
+    engine.dispose()
+
+
+def run_tidy(client, entrypoint):
+    if entrypoint == "action":
+        return asyncio.run(actions.run_auto_sort("alice", skip_llm=True))
+    response = client.post("/api/sessions/auto-sort?skip_llm=true")
+    assert response.status_code == 200, response.text
+    return response.json()
+
+
+@pytest.mark.parametrize("entrypoint", ["route", "action"])
+@pytest.mark.parametrize("title,prompt", [
+    ("New chat", "Please analyze the following contract and retain all details. " * 20),
+    ("Contract analysis", "Review contract"),
+    ("Chat: analysis", "Explain these results and retain the full answer"),
+    ("Test", "Here is a large input that should be analyzed and retained"),
+], ids=["generic-title", "short-prompt", "title-prefix", "test-title"])
+def test_tidy_preserves_nontrivial_saved_answer(tidy_api, title, prompt, entrypoint):
+    client, factory, manager = tidy_api
+    old = datetime.now(timezone.utc).replace(tzinfo=None) - timedelta(hours=2)
+    answer = "Clause analysis and recommended changes.\n" * 2000
+    with factory() as db:
+        db.add(database.Session(
+            id="valuable-chat", name=title, owner="alice", endpoint_url="", model="",
+            archived=False, is_important=False, message_count=2,
+            created_at=old, updated_at=old, last_accessed=old, last_message_at=old,
+        ))
+        db.commit()
+        db.add_all([
+            database.ChatMessage(id="prompt", session_id="valuable-chat", role="user",
+                                 content=prompt, timestamp=old),
+            database.ChatMessage(id="answer", session_id="valuable-chat", role="assistant",
+                                 content=answer, timestamp=old + timedelta(seconds=1)),
+        ])
+        db.commit()
+    run_tidy(client, entrypoint)
+    with factory() as db:
+        remaining = db.query(database.ChatMessage).filter_by(session_id="valuable-chat").count()
+        survives = db.get(database.Session, "valuable-chat") is not None
+    assert survives and remaining == 2, "Title/prompt heuristics must not erase saved answers"
+    with factory() as db:
+        assert db.get(database.ChatMessage, "answer").content == answer
+
+
+@pytest.mark.parametrize("entrypoint", ["route", "action"])
+@pytest.mark.parametrize("kind", ["unanswered", "greeting", "empty", "fresh-empty", "starred-empty", "archived", "other-owner", "incognito"])
+def test_tidy_cleanup_boundaries(tidy_api, entrypoint, kind):
+    client, factory, manager = tidy_api
+    now = datetime.now(timezone.utc).replace(tzinfo=None)
+    timestamp = now if kind == "fresh-empty" else now - timedelta(hours=2)
+    message = kind in {"unanswered", "greeting", "archived", "other-owner", "incognito"}
+    with factory() as db:
+        db.add(database.Session(
+            id="boundary-chat", name="Incognito" if kind == "incognito" else "New chat",
+            owner="bob" if kind == "other-owner" else "alice", endpoint_url="", model="",
+            archived=kind == "archived", is_important=kind == "starred-empty",
+            # Deliberately inaccurate metadata: cleanup must use message rows.
+            message_count=0 if message else 40,
+            created_at=timestamp, updated_at=timestamp, last_accessed=timestamp, last_message_at=timestamp,
+        ))
+        db.commit()
+        if message:
+            db.add(database.ChatMessage(id="boundary-message", session_id="boundary-chat", role="user",
+                                        content="hi" if kind == "greeting" else "Pending question " * 100,
+                                        timestamp=timestamp))
+            db.commit()
+    run_tidy(client, entrypoint)
+    deleted = kind in {"empty", "incognito"}
+    with factory() as db:
+        assert (db.get(database.Session, "boundary-chat") is None) == deleted
+        assert db.query(database.ChatMessage).filter_by(session_id="boundary-chat").count() == int(message and not deleted)
+
+
+@pytest.mark.parametrize("entrypoint", ["route", "action"])
+def test_tidy_keeps_folder_assignment_working(tidy_api, monkeypatch, entrypoint):
+    from types import SimpleNamespace
+    import src.llm_core as llm
+    import src.task_endpoint as endpoints
+    client, factory, manager = tidy_api
+    old = datetime.now(timezone.utc).replace(tzinfo=None) - timedelta(hours=2)
+    for sid in ["chat-one-long-id", "chat-two-long-id"]:
+        with factory() as db:
+            db.add(database.Session(id=sid, name="New chat", owner="alice", endpoint_url="", model="",
+                                    archived=False, created_at=old, updated_at=old,
+                                    last_accessed=old, last_message_at=old))
+            db.commit()
+            db.add(database.ChatMessage(id=f"{sid}-message", session_id=sid, role="user",
+                                        content="Saved question", timestamp=old))
+            db.commit()
+        manager.sessions[sid] = SimpleNamespace(id=sid, name="New chat", archived=False,
+                                                updated_at=old.isoformat(), created_at=old.isoformat())
+    monkeypatch.setattr(manager, "get_sessions_for_user", lambda owner: manager.sessions)
+    monkeypatch.setattr(endpoints, "resolve_task_endpoint", lambda **kwargs: ("http://model.invalid", "test", {}))
+    response_text = '{"folders":{"Projects":["chat-one","chat-two"]}}'
+    monkeypatch.setattr(llm, "llm_call", lambda *args, **kwargs: response_text)
+
+    async def async_response(*args, **kwargs):
+        return response_text
+
+    monkeypatch.setattr(llm, "llm_call_async", async_response)
+    if entrypoint == "action":
+        result = asyncio.run(actions.run_auto_sort("alice"))
+        assert "Sorted 2 sessions" in result
+    else:
+        response = client.post("/api/sessions/auto-sort")
+        assert response.status_code == 200, response.text
+        assert response.json()["updated"] == 2
+    with factory() as db:
+        assert db.query(database.ChatMessage).count() == 2
+        assert {row.folder for row in db.query(database.Session).all()} == {"Projects"}

tests/test_session_actions_cleanup.py

@@ -128,7 +128,7 @@ def test_auto_sort_keeps_fresh_session_while_first_response_is_pending(monkeypat
         db.close()
 
 
-def test_auto_sort_still_deletes_old_throwaway_sessions(monkeypatch):
+def test_auto_sort_keeps_old_nonempty_sessions_even_with_throwaway_title(monkeypatch):
     session_factory = _make_session_factory()
     _install_session_factory(monkeypatch, session_factory)
 
@@ -160,7 +160,8 @@ def test_auto_sort_still_deletes_old_throwaway_sessions(monkeypatch):
 
     db = session_factory()
     try:
-        assert db.query(DbSession).filter(DbSession.id == sid).first() is None
+        assert db.query(DbSession).filter(DbSession.id == sid).first() is not None
-        assert "Cleaned 1 sessions" in result
+        assert db.query(DbMessage).filter(DbMessage.session_id == sid).count() == 1
+        assert "Cleaned 0 sessions" in result
     finally:
         db.close()

tests/test_session_list_owner_scope.py

@@ -19,6 +19,7 @@ from core.database import ChatMessage as DbMessage
 from core.database import Session as DbSession
 
 _TMPDB = tempfile.NamedTemporaryFile(suffix=".db", delete=False)
+_TMPDB.close()  # SQLite owns its connections; release the Windows file handle.
 _ENGINE = create_engine(
     f"sqlite:///{_TMPDB.name}",
     connect_args={"check_same_thread": False},
@@ -230,12 +231,14 @@ def test_patch_session_updates_persisted_cwd(monkeypatch):
 
 def test_auto_sort_skip_llm_cleans_owner_stamped_sessions_when_auth_disabled(monkeypatch):
     import routes.session_routes as sr
+    from fastapi import APIRouter
     from unittest.mock import MagicMock
 
     _stub_multipart_if_missing(monkeypatch)
     monkeypatch.setenv("AUTH_ENABLED", "false")
     monkeypatch.setattr(sr, "SessionLocal", _TS)
     monkeypatch.setattr(sr, "effective_user", lambda request: None)
+    monkeypatch.setattr(sr, "router", APIRouter(prefix="/api"))
 
     sid = str(uuid.uuid4())
     old_time = cdb.utcnow_naive() - timedelta(hours=2)
@@ -250,19 +253,12 @@ def test_auto_sort_skip_llm_cleans_owner_stamped_sessions_when_auth_disabled(mon
             endpoint_url="http://localhost",
             model="gpt-4",
             archived=False,
-            message_count=1,
+            message_count=0,
             created_at=old_time,
             updated_at=old_time,
             last_message_at=old_time,
             last_accessed=old_time,
         ))
-        db.add(DbMessage(
-            id="m-" + uuid.uuid4().hex,
-            session_id=sid,
-            role="user",
-            content="hi",
-            timestamp=old_time,
-        ))
         db.commit()
     finally:
         db.close()
@@ -270,6 +266,13 @@ def test_auto_sort_skip_llm_cleans_owner_stamped_sessions_when_auth_disabled(mon
     session = MagicMock(id=sid, name="New chat", model="gpt-4", endpoint_url="http://localhost", rag=False, archived=False)
     sm = MagicMock()
     sm.get_sessions_for_user.return_value = {sid: session}
+
+    def delete_session(session_id):
+        with _TS() as db:
+            db.query(DbSession).filter(DbSession.id == session_id).delete()
+            db.commit()
+
+    sm.delete_session.side_effect = delete_session
     router = sr.setup_session_routes(sm, {})
     endpoint = next(r.endpoint for r in router.routes
                     if getattr(r, "path", "") == "/api/sessions/auto-sort"
@@ -277,7 +280,8 @@ def test_auto_sort_skip_llm_cleans_owner_stamped_sessions_when_auth_disabled(mon
 
     result = endpoint(request=MagicMock(), skip_llm=True)
 
-    assert result["deleted_throwaway"] == 1
+    assert result["deleted_empty"] == 1
+    assert result["deleted_throwaway"] == 0
     db = _TS()
     try:
         assert db.query(DbSession).filter(DbSession.id == sid).first() is None