diff --git a/lib/tasks/__tests__/enrichTasks.test.ts b/lib/tasks/__tests__/enrichTasks.test.ts
index 5ba06b33..41f9b488 100644
--- a/lib/tasks/__tests__/enrichTasks.test.ts
+++ b/lib/tasks/__tests__/enrichTasks.test.ts
@@ -79,6 +79,7 @@ describe("enrichTasks", () => {
         upcoming: ["2026-03-27T09:00:00Z", "2026-04-03T09:00:00Z"],
         owner_email: "owner@example.com",
         timezone: "America/New_York",
+        trigger_lookup_failed: false,
       },
     ]);
     expect(fetchTriggerRuns).toHaveBeenCalledWith({ "filter[schedule]": "sched_abc" }, 5);
@@ -99,6 +100,7 @@ describe("enrichTasks", () => {
         upcoming: [],
         owner_email: null,
         timezone: null,
+        trigger_lookup_failed: false,
       },
     ]);
     expect(fetchTriggerRuns).not.toHaveBeenCalled();
@@ -118,6 +120,7 @@ describe("enrichTasks", () => {
         upcoming: [],
         owner_email: null,
         timezone: null,
+        trigger_lookup_failed: true,
       },
     ]);
   });
@@ -136,8 +139,33 @@ describe("enrichTasks", () => {
         upcoming: [],
         owner_email: null,
         timezone: "UTC",
+        trigger_lookup_failed: false,
       },
     ]);
     expect(retrieveTaskRun).not.toHaveBeenCalled();
   });
+
+  it("flags trigger_lookup_failed when the Trigger lookup throws (chat#1918)", async () => {
+    vi.mocked(fetchTriggerRuns).mockRejectedValue(new Error("Trigger API 503"));
+    vi.mocked(retrieveScheduleTimezone).mockResolvedValue(null as never);
+    vi.mocked(selectAccountEmails).mockResolvedValue([] as never);
+    const [enriched] = await enrichTasks([mockTask]);
+    expect(enriched.trigger_lookup_failed).toBe(true);
+    expect(enriched.upcoming).toEqual([]);
+  });
+
+  it("does NOT flag a live schedule that legitimately has no runs yet", async () => {
+    vi.mocked(fetchTriggerRuns).mockResolvedValue([] as never);
+    vi.mocked(retrieveScheduleTimezone).mockResolvedValue("UTC" as never);
+    vi.mocked(selectAccountEmails).mockResolvedValue([] as never);
+    const [enriched] = await enrichTasks([mockTask]);
+    expect(enriched.trigger_lookup_failed).toBe(false);
+    expect(enriched.upcoming).toEqual([]);
+  });
+
+  it("does NOT flag a task that has no trigger_schedule_id to look up", async () => {
+    vi.mocked(selectAccountEmails).mockResolvedValue([] as never);
+    const [enriched] = await enrichTasks([{ ...mockTask, trigger_schedule_id: null }]);
+    expect(enriched.trigger_lookup_failed).toBe(false);
+  });
 });
diff --git a/lib/tasks/enrichTasks.ts b/lib/tasks/enrichTasks.ts
index b8eece49..5be7ab12 100644
--- a/lib/tasks/enrichTasks.ts
+++ b/lib/tasks/enrichTasks.ts
@@ -12,12 +12,20 @@ export type EnrichedTask = ScheduledAction & {
   owner_email: string | null;
   /** IANA timezone read from the Trigger.dev schedule (source of truth); null when unavailable. */
   timezone: string | null;
+  /**
+   * True when the Trigger.dev lookup errored, so `recent_runs` / `upcoming` /
+   * `timezone` are not authoritative. Without this, a failed lookup and a live
+   * schedule with no runs yet were both an empty `upcoming` — which got a live
+   * schedule misdiagnosed as dead and a duplicate task created (chat#1918).
+   */
+  trigger_lookup_failed: boolean;
 };
 
 interface TriggerInfo {
   recent_runs: TriggerRun[];
   upcoming: string[];
   timezone: string | null;
+  trigger_lookup_failed: boolean;
 }
 
 type TriggerInfoEntry = readonly [string, TriggerInfo];
@@ -34,7 +42,10 @@ export async function enrichTasks(tasks: ScheduledAction[]): Promise<EnrichedTas
       const scheduleId = task.trigger_schedule_id;
 
       if (!scheduleId) {
-        return [task.id, { recent_runs: [], upcoming: [], timezone: null }] as const;
+        return [
+          task.id,
+          { recent_runs: [], upcoming: [], timezone: null, trigger_lookup_failed: false },
+        ] as const;
       }
 
       try {
@@ -64,11 +75,19 @@ export async function enrichTasks(tasks: ScheduledAction[]): Promise<EnrichedTas
 
         return [
           task.id,
-          { recent_runs: recentRuns, upcoming, timezone: timezone ?? null },
+          {
+            recent_runs: recentRuns,
+            upcoming,
+            timezone: timezone ?? null,
+            trigger_lookup_failed: false,
+          },
         ] as const;
       } catch {
-        // Trigger.dev API failed — return task without trigger enrichment
-        return [task.id, { recent_runs: [], upcoming: [], timezone: null }] as const;
+        // Trigger.dev API failed — the enrichment fields are unknown, not empty.
+        return [
+          task.id,
+          { recent_runs: [], upcoming: [], timezone: null, trigger_lookup_failed: true },
+        ] as const;
       }
     }),
   );