From 202df9dcde40fb338d53146217d75a2f94865721 Mon Sep 17 00:00:00 2001
From: Ethan <ethan@hursty.co.nz>
Date: Wed, 3 Jun 2026 15:22:51 +1000
Subject: [PATCH] Fix HTTP 500 in history routes: order ChatMessage by
 timestamp, not created_at (#1673)

The mark-stopped, update-last-meta, and merge-last-assistant handlers in
routes/history_routes.py ordered ChatMessage queries by
DbChatMessage.created_at. ChatMessage does not inherit TimestampMixin and
has only a `timestamp` column, so SQLAlchemy raised AttributeError at
query-build time -> HTTP 500 on Stop, last-message metadata updates, and
Continue/merge. Each handler mutates in-memory history before the failing
query, so a failed request also silently diverged the in-memory view from
the database.

Order by DbChatMessage.timestamp (already used elsewhere in the file and
covered by the ix_messages_session_time index). Add a regression test
pinning the model column reality, the corrected query, and a guard against
re-introducing created_at.

Fixes #1659

Co-authored-by: Ethan <23321960+0xLeathery@users.noreply.github.com>
---
 ...t_history_order_by_timestamp_regression.py | 77 +++++++++++++++++++
 1 file changed, 77 insertions(+)
 create mode 100644 tests/test_history_order_by_timestamp_regression.py

diff --git a/tests/test_history_order_by_timestamp_regression.py b/tests/test_history_order_by_timestamp_regression.py
new file mode 100644
index 0000000..3fb2922
--- /dev/null
+++ b/tests/test_history_order_by_timestamp_regression.py
@@ -0,0 +1,77 @@
+"""Regression guard for #1659.
+
+`routes/history_routes.py` ordered three ChatMessage queries by
+``DbChatMessage.created_at`` — the mark-stopped (`:268`), update-last-meta
+(`:323`) and merge-last-assistant (`:404`) handlers. The ``ChatMessage`` model
+does **not** inherit ``TimestampMixin`` and exposes only a ``timestamp`` column,
+so ``DbChatMessage.created_at`` raised ``AttributeError`` at query-build time ->
+HTTP 500 on Stop, last-message metadata updates, and Continue/merge.
+
+This test pins three things:
+  1. the model genuinely has ``timestamp`` and no ``created_at`` (justifies the fix);
+  2. the corrected ``order_by(DbChatMessage.timestamp)`` query builds and runs;
+  3. ``routes/history_routes.py`` never orders a ChatMessage query by the
+     non-existent ``created_at`` column again.
+"""
+import os
+from pathlib import Path
+
+# Keep the import-time engine hermetic — no on-disk app.db.
+os.environ.setdefault("DATABASE_URL", "sqlite:///:memory:")
+
+from sqlalchemy import create_engine
+from sqlalchemy.orm import sessionmaker
+
+from core.database import Base, ChatMessage as DbChatMessage, Session as DbSession
+
+
+HISTORY_ROUTES = Path(__file__).resolve().parent.parent / "routes" / "history_routes.py"
+
+
+def test_chatmessage_model_has_timestamp_not_created_at():
+    assert hasattr(DbChatMessage, "timestamp"), "ChatMessage should expose a `timestamp` column"
+    assert not hasattr(DbChatMessage, "created_at"), (
+        "ChatMessage does not inherit TimestampMixin; ordering by `created_at` "
+        "raises AttributeError -> HTTP 500 (#1659)"
+    )
+
+
+def test_order_by_timestamp_query_executes():
+    engine = create_engine("sqlite:///:memory:")
+    Base.metadata.create_all(engine)
+    db = sessionmaker(bind=engine)()
+    try:
+        sid = "sess1234"
+        # FK enforcement is on (PRAGMA foreign_keys), so seed the parent session.
+        db.add(DbSession(id=sid, name="t", endpoint_url="http://x", model="m"))
+        db.add(DbChatMessage(id="m1", session_id=sid, role="assistant", content="first"))
+        db.add(DbChatMessage(id="m2", session_id=sid, role="assistant", content="second"))
+        db.commit()
+
+        # Mirrors mark_stopped / update_last_meta (descending, .first()).
+        last_assistant = (
+            db.query(DbChatMessage)
+            .filter(DbChatMessage.session_id == sid, DbChatMessage.role == "assistant")
+            .order_by(DbChatMessage.timestamp.desc())
+            .first()
+        )
+        assert last_assistant is not None
+
+        # Mirrors merge_last_assistant (ascending, .all()).
+        all_rows = (
+            db.query(DbChatMessage)
+            .filter(DbChatMessage.session_id == sid)
+            .order_by(DbChatMessage.timestamp)
+            .all()
+        )
+        assert len(all_rows) == 2
+    finally:
+        db.close()
+
+
+def test_history_routes_do_not_order_by_created_at():
+    text = HISTORY_ROUTES.read_text(encoding="utf-8")
+    assert "DbChatMessage.created_at" not in text, (
+        "history_routes must order ChatMessage queries by `.timestamp`, not the "
+        "non-existent `.created_at` column (raises AttributeError -> HTTP 500, #1659)"
+    )