From 60fcec99eb061bdc7f5ca80615acace1eb446a94 Mon Sep 17 00:00:00 2001
From: Slava Trofimov <slava@trofimov.ca>
Date: Tue, 2 Jun 2026 09:30:45 -0400
Subject: [PATCH] fix websocket chat history ordering

---
 src/octopal/infrastructure/store/sqlite.py |  2 +-
 tests/test_memory_system.py                | 37 ++++++++++++++++++++++
 2 files changed, 38 insertions(+), 1 deletion(-)

diff --git a/src/octopal/infrastructure/store/sqlite.py b/src/octopal/infrastructure/store/sqlite.py
index e8204450..69f22418 100644
--- a/src/octopal/infrastructure/store/sqlite.py
+++ b/src/octopal/infrastructure/store/sqlite.py
@@ -918,7 +918,7 @@ def list_memory_entries_for_owner(self, owner_id: str, limit: int = 200) -> list
 
     def list_memory_entries_by_chat(self, chat_id: int, limit: int = 50) -> list[MemoryEntry]:
         cursor = self._conn.execute(
-            "SELECT * FROM memory_entries WHERE chat_id = ? ORDER BY id DESC LIMIT ?",
+            "SELECT * FROM memory_entries WHERE chat_id = ? ORDER BY created_at DESC, rowid DESC LIMIT ?",
             (chat_id, limit),
         )
         return [self._row_to_memory(row) for row in cursor.fetchall()]
diff --git a/tests/test_memory_system.py b/tests/test_memory_system.py
index 0b613627..36e51d51 100644
--- a/tests/test_memory_system.py
+++ b/tests/test_memory_system.py
@@ -2,6 +2,7 @@
 
 import asyncio
 import uuid
+from datetime import UTC, datetime, timedelta
 from pathlib import Path
 
 from octopal.infrastructure.store.models import MemoryEntry
@@ -58,6 +59,42 @@ def test_memory_owner_filter(tmp_path: Path) -> None:
     assert rows[0].content == "owned by default"
 
 
+def test_memory_chat_history_orders_by_created_at_not_uuid(tmp_path: Path) -> None:
+    store = SQLiteStore(_StoreSettings(tmp_path / "data", tmp_path / "workspace"))
+    base = datetime(2026, 6, 2, 12, 0, tzinfo=UTC)
+    entries = [
+        MemoryEntry(
+            id="ffffeeee-dddd-cccc-bbbb-aaaaaaaaaaaa",
+            role="user",
+            content="oldest",
+            embedding=None,
+            created_at=base,
+            metadata={"owner_id": "default", "chat_id": 7},
+        ),
+        MemoryEntry(
+            id="11112222-3333-4444-5555-666677778888",
+            role="assistant",
+            content="newest",
+            embedding=None,
+            created_at=base + timedelta(minutes=2),
+            metadata={"owner_id": "default", "chat_id": 7},
+        ),
+        MemoryEntry(
+            id="9999aaaa-bbbb-cccc-dddd-eeeeffffffff",
+            role="user",
+            content="middle",
+            embedding=None,
+            created_at=base + timedelta(minutes=1),
+            metadata={"owner_id": "default", "chat_id": 7},
+        ),
+    ]
+    for entry in entries:
+        store.add_memory_entry(entry)
+
+    rows = store.list_memory_entries_by_chat(7, limit=3)
+    assert [row.content for row in rows] == ["newest", "middle", "oldest"]
+
+
 def test_canon_event_log_and_compaction(tmp_path: Path) -> None:
     canon = CanonService(
         workspace_dir=tmp_path / "workspace",