The conversations fix

application/api/user/agents/routes.py

@@ -28,6 +28,7 @@ from application.api.user.team_sharing import (
 )
 from application.storage.db.repositories.agent_folders import AgentFoldersRepository
 from application.storage.db.repositories.agents import AgentsRepository
+from application.storage.db.repositories.conversations import ConversationsRepository
 from application.storage.db.repositories.stack_logs import StackLogsRepository
 from application.storage.db.repositories.token_usage import TokenUsageRepository
 from application.storage.db.repositories.users import UsersRepository
@@ -1359,19 +1360,22 @@ class RegenerateAgentKey(Resource):
                         500,
                     )
 
-                # Re-point key-string history to the new key. conversations,
-                # token_usage and stack_logs (since 0026) all carry agent_id, so
-                # per-agent analytics survive rotation via agent_id regardless.
-                # These rewrites still run to (a) preserve the 24h rate-limit
-                # window, which is keyed by api_key only (token_usage), and (b)
-                # keep the api_key column consistent / re-attach any legacy rows
-                # whose agent_id is NULL. Runs in the same transaction as the swap.
+                # Re-point key-string history to the new key so per-agent
+                # analytics survive rotation. token_usage/stack_logs (0026)
+                # carry agent_id, but rows can still be api_key-only:
+                # conversations set api_key without an agent_id unless the caller
+                # passes one, stack_logs rows may have a NULL agent_id, and the
+                # 24h rate-limit window is keyed by api_key only (token_usage).
+                # All three rewrites run in the same transaction as the swap.
                 StackLogsRepository(conn).reassign_api_key(
                     old_key=old_key, new_key=new_key
                 )
                 TokenUsageRepository(conn).reassign_api_key(
                     old_key=old_key, new_key=new_key
                 )
+                ConversationsRepository(conn).reassign_api_key(
+                    old_key=old_key, new_key=new_key
+                )
         except Exception as err:
             current_app.logger.error(
                 f"Error regenerating agent key: {err}", exc_info=True

application/storage/db/repositories/conversations.py

@@ -574,6 +574,27 @@ class ConversationsRepository:
         self._reap_artifact_storage(paths)
         return result.rowcount
 
+    def reassign_api_key(self, *, old_key: str, new_key: str) -> int:
+        """Re-point conversation rows from ``old_key`` to ``new_key``.
+
+        Called when an agent's key is rotated. Per-agent analytics match
+        ``c.api_key = :api_key OR c.agent_id = :agent_pg_id``, but a
+        conversation created from api-key traffic may have ``api_key`` set and
+        ``agent_id`` NULL (``conversation_service`` only sets ``agent_id`` when
+        the caller passes one). Rewriting ``api_key`` keeps those rows attached
+        to the agent after rotation instead of orphaning them.
+
+        Matched by ``api_key`` only — ``agents.key`` is globally unique so a key
+        maps to exactly one agent. Returns the number of rows updated.
+        """
+        if not old_key or not new_key:
+            return 0
+        result = self._conn.execute(
+            text("UPDATE conversations SET api_key = :new_key WHERE api_key = :old_key"),
+            {"old_key": old_key, "new_key": new_key},
+        )
+        return result.rowcount
+
     @staticmethod
     def _reap_artifact_storage(paths: list) -> None:
         """Best-effort delete artifact bytes whose rows were cascade-removed; never raises."""

tests/api/user/agents/test_routes_happy.py

@@ -1343,11 +1343,16 @@ class TestRegenerateAgentKey:
         assert repo.find_by_key(new_key)["id"] == agent["id"]
 
     def test_migrates_historical_logs_and_usage(self, app, pg_conn):
-        """stack_logs + token_usage rows follow the key so analytics and the
-        rate-limit window are not orphaned. The stack_logs row is stamped with
-        a *different* user_id (a caller, not the owner) to prove the migration
-        is not owner-scoped."""
+        """stack_logs + token_usage + conversations rows follow the key so
+        analytics and the rate-limit window are not orphaned. The stack_logs row
+        is stamped with a *different* user_id (a caller, not the owner) to prove
+        the migration is not owner-scoped, and the conversation is created with
+        api_key set but agent_id NULL to prove the api_key-only path is covered.
+        """
         from application.api.user.agents.routes import RegenerateAgentKey
+        from application.storage.db.repositories.conversations import (
+            ConversationsRepository,
+        )
         from application.storage.db.repositories.stack_logs import (
             StackLogsRepository,
         )
@@ -1369,6 +1374,10 @@ class TestRegenerateAgentKey:
         TokenUsageRepository(pg_conn).insert(
             api_key=old_key, prompt_tokens=7, generated_tokens=3,
         )
+        # api_key set, agent_id intentionally omitted (NULL) — the orphan case.
+        ConversationsRepository(pg_conn).create(
+            user, "conv", api_key=old_key,
+        )
 
         with _patch_db(pg_conn), app.test_request_context(
             f"/api/regenerate_agent_key/{agent['id']}", method="POST"
@@ -1380,24 +1389,19 @@ class TestRegenerateAgentKey:
         new_key = response.json["key"]
 
         from sqlalchemy import text
-        stack_old = pg_conn.execute(
-            text("SELECT COUNT(*) FROM stack_logs WHERE api_key = :k"),
-            {"k": old_key},
-        ).scalar()
-        stack_new = pg_conn.execute(
-            text("SELECT COUNT(*) FROM stack_logs WHERE api_key = :k"),
-            {"k": new_key},
-        ).scalar()
-        usage_old = pg_conn.execute(
-            text("SELECT COUNT(*) FROM token_usage WHERE api_key = :k"),
-            {"k": old_key},
-        ).scalar()
-        usage_new = pg_conn.execute(
-            text("SELECT COUNT(*) FROM token_usage WHERE api_key = :k"),
-            {"k": new_key},
-        ).scalar()
-        assert stack_old == 0 and stack_new == 1
-        assert usage_old == 0 and usage_new == 1
+
+        def _count(table, key):
+            return pg_conn.execute(
+                text(f"SELECT COUNT(*) FROM {table} WHERE api_key = :k"),
+                {"k": key},
+            ).scalar()
+
+        assert _count("stack_logs", old_key) == 0
+        assert _count("stack_logs", new_key) == 1
+        assert _count("token_usage", old_key) == 0
+        assert _count("token_usage", new_key) == 1
+        assert _count("conversations", old_key) == 0
+        assert _count("conversations", new_key) == 1
 
     def test_db_error_returns_500(self, app):
         from application.api.user.agents.routes import RegenerateAgentKey

tests/storage/db/repositories/test_conversations.py

@@ -885,3 +885,32 @@ class TestUuidShapeGate:
         msg = repo.get_message_at(conv["id"], 0)
         assert msg is not None
         assert msg["prompt"] == "q"
+
+
+class TestReassignApiKey:
+    def test_rewrites_matching_rows_including_null_agent(self, pg_conn):
+        # A conversation created from api-key traffic can have api_key set and
+        # agent_id NULL; on key rotation it must follow the key so per-agent
+        # analytics (api_key OR agent_id) don't orphan it.
+        repo = _repo(pg_conn)
+        repo.create("owner", "c1", api_key="conv-old")
+        repo.create("caller", "c2", api_key="conv-old")
+        repo.create("owner", "c3", api_key="conv-other")
+
+        moved = repo.reassign_api_key(old_key="conv-old", new_key="conv-new")
+        assert moved == 2
+
+        assert pg_conn.execute(
+            text("SELECT COUNT(*) FROM conversations WHERE api_key = 'conv-old'")
+        ).scalar() == 0
+        assert pg_conn.execute(
+            text("SELECT COUNT(*) FROM conversations WHERE api_key = 'conv-new'")
+        ).scalar() == 2
+        assert pg_conn.execute(
+            text("SELECT COUNT(*) FROM conversations WHERE api_key = 'conv-other'")
+        ).scalar() == 1
+
+    def test_noop_on_blank_keys(self, pg_conn):
+        repo = _repo(pg_conn)
+        assert repo.reassign_api_key(old_key="", new_key="x") == 0
+        assert repo.reassign_api_key(old_key="x", new_key="") == 0