diff --git a/hermes_cli/web_server.py b/hermes_cli/web_server.py
index c5978ebfff4..5645f91ddf7 100644
--- a/hermes_cli/web_server.py
+++ b/hermes_cli/web_server.py
@@ -9306,7 +9306,7 @@ def _session_latest_descendant(session_id: str, db):
             """
             WITH RECURSIVE descendants(id, parent_session_id, started_at) AS (
                 SELECT id, parent_session_id, started_at FROM sessions WHERE id = ?
-                UNION ALL
+                UNION
                 SELECT s.id, s.parent_session_id, s.started_at
                 FROM sessions s
                 JOIN descendants d ON s.parent_session_id = d.id
diff --git a/tests/hermes_cli/test_web_server.py b/tests/hermes_cli/test_web_server.py
index 748800ca1b2..c67371b4e33 100644
--- a/tests/hermes_cli/test_web_server.py
+++ b/tests/hermes_cli/test_web_server.py
@@ -1138,6 +1138,29 @@ class TestWebServerEndpoints:
         assert worker_resp.status_code == 200
         assert worker_resp.json()["session_id"] == "worker-tip"
 
+    def test_latest_descendant_survives_parent_cycle(self):
+        """Regression for the #39140 CTE salvage: a corrupted parent chain
+        that loops (a -> b -> a) must terminate (UNION dedup) instead of
+        recursing forever like UNION ALL would."""
+        from hermes_state import SessionDB
+
+        db = SessionDB()
+        try:
+            db.create_session(session_id="cyc-a", source="cli")
+            db.create_session(
+                session_id="cyc-b", source="cli", parent_session_id="cyc-a"
+            )
+            db._conn.execute(
+                "UPDATE sessions SET parent_session_id='cyc-b' WHERE id='cyc-a'"
+            )
+            db._conn.commit()
+        finally:
+            db.close()
+
+        resp = self.client.get("/api/sessions/cyc-a/latest-descendant")
+        assert resp.status_code == 200
+        assert resp.json()["session_id"] == "cyc-b"
+
     def test_analytics_endpoints_read_requested_profile(self):
         from hermes_state import SessionDB
         from hermes_cli import profiles as profiles_mod