Revert "fix(chats): preserve saved conversations during tidy"

routes/session_routes.py

@@ -1315,7 +1315,7 @@ 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/Incognito sessions and Phase 2 asks the LLM
+        Phase 1 deletes empty/throwaway 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.
@@ -1326,11 +1326,21 @@ def setup_session_routes(
         single_user_mode = not user and _auth_disabled()
         user_sessions = session_manager.get_sessions_for_user(user)
 
-        # Saved conversations are never disposable based on their title or prompt.
+        # Delete empty and throwaway sessions before sorting
         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:
@@ -1339,11 +1349,15 @@ 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 one aggregate query
+            # Precompute per-session message counts in TWO aggregate queries
             # 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
@@ -1353,10 +1367,9 @@ 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
@@ -1365,11 +1378,31 @@ 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

@@ -12,6 +12,16 @@ 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
 
@@ -44,15 +54,14 @@ 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:
-    """Remove empty/Incognito sessions and optionally organize saved chats.
+    """Run session cleanup + (optional) AI folder sort for the given owner.
 
     Args:
         owner: user whose sessions to process
-        skip_llm: when True, do only Phase 1 (delete empty/Incognito sessions);
+        skip_llm: when True, do only Phase 1 (delete empty/throwaway sessions);
             skip Phase 2 (AI folder assignment). Used by the built-in daily
             background sweep so it never burns LLM tokens.
-        delete_throwaway: retained for caller compatibility. Ordinary sessions
-            with saved messages are always preserved, regardless of this flag.
+        delete_throwaway: when False, only empty/incognito sessions are deleted.
 
     Returns a human-readable summary of what was done.
     """
@@ -62,7 +71,7 @@ async def run_auto_sort(owner: str, skip_llm: bool = False, delete_throwaway: bo
 
     db = SessionLocal()
     try:
-        # ── Phase 1: Delete only empty and explicitly Incognito sessions ──
+        # ── Phase 1: Delete empty/throwaway sessions ──
         deleted_empty = 0
         deleted_throwaway = 0
 
@@ -84,13 +93,47 @@ async def run_auto_sort(owner: str, skip_llm: bool = False, delete_throwaway: bo
             if is_session_recently_active(row, now=cleanup_now):
                 continue
 
-            has_messages = db.query(DbMsg.id).filter(
+            msg_count = db.query(DbMsg.id).filter(
                 DbMsg.session_id == row.id
-            ).first() is not None
-            if not has_messages:
+            ).limit(_THROWAWAY_MAX_MESSAGES + 1).count()
+            should_delete = False
+
+            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

@@ -1,148 +0,0 @@
-"""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 *args, **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_keeps_old_nonempty_sessions_even_with_throwaway_title(monkeypatch):
+def test_auto_sort_still_deletes_old_throwaway_sessions(monkeypatch):
     session_factory = _make_session_factory()
     _install_session_factory(monkeypatch, session_factory)
 
@@ -160,8 +160,7 @@ def test_auto_sort_keeps_old_nonempty_sessions_even_with_throwaway_title(monkeyp
 
     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
+        assert db.query(DbSession).filter(DbSession.id == sid).first() is None
+        assert "Cleaned 1 sessions" in result
     finally:
         db.close()

tests/test_session_list_owner_scope.py

@@ -19,7 +19,6 @@ 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},
@@ -231,14 +230,12 @@ 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)
@@ -253,12 +250,19 @@ 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=0,
+            message_count=1,
             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()
@@ -266,13 +270,6 @@ 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"
@@ -280,8 +277,7 @@ def test_auto_sort_skip_llm_cleans_owner_stamped_sessions_when_auth_disabled(mon
 
     result = endpoint(request=MagicMock(), skip_llm=True)
 
-    assert result["deleted_empty"] == 1
-    assert result["deleted_throwaway"] == 0
+    assert result["deleted_throwaway"] == 1
     db = _TS()
     try:
         assert db.query(DbSession).filter(DbSession.id == sid).first() is None