diff --git a/packages/ai/src/chatTransport.test.ts b/packages/ai/src/chatTransport.test.ts
index cba7d672a..5a80b3117 100644
--- a/packages/ai/src/chatTransport.test.ts
+++ b/packages/ai/src/chatTransport.test.ts
@@ -546,6 +546,70 @@ describe("TriggerChatTransport", function () {
     expect(runStore.get("chat-inactive")).toBeUndefined();
   });
 
+  it("reports inactive reconnect cleanup delete failures through onError", async function () {
+    const errors: TriggerChatTransportError[] = [];
+    const runStore = new FailingCleanupDeleteRunStore(1);
+    runStore.set({
+      chatId: "chat-inactive-delete-failure",
+      runId: "run_inactive_delete_failure",
+      publicAccessToken: "pk_inactive_delete_failure",
+      streamKey: "chat-stream",
+      lastEventId: "10-0",
+      isActive: false,
+    });
+
+    const transport = new TriggerChatTransport({
+      task: "chat-task",
+      stream: "chat-stream",
+      accessToken: "pk_trigger",
+      runStore,
+      onError: function onError(error) {
+        errors.push(error);
+      },
+    });
+
+    const stream = await transport.reconnectToStream({
+      chatId: "chat-inactive-delete-failure",
+    });
+
+    expect(stream).toBeNull();
+    expect(errors).toHaveLength(1);
+    expect(errors[0]).toMatchObject({
+      phase: "reconnect",
+      chatId: "chat-inactive-delete-failure",
+      runId: "run_inactive_delete_failure",
+    });
+    expect(errors[0]?.error.message).toBe("cleanup delete failed");
+  });
+
+  it("returns null when inactive reconnect cleanup delete and onError both fail", async function () {
+    const runStore = new FailingCleanupDeleteRunStore(1);
+    runStore.set({
+      chatId: "chat-inactive-delete-onerror-failure",
+      runId: "run_inactive_delete_onerror_failure",
+      publicAccessToken: "pk_inactive_delete_onerror_failure",
+      streamKey: "chat-stream",
+      lastEventId: "10-0",
+      isActive: false,
+    });
+
+    const transport = new TriggerChatTransport({
+      task: "chat-task",
+      stream: "chat-stream",
+      accessToken: "pk_trigger",
+      runStore,
+      onError: async function onError() {
+        throw new Error("onError failed");
+      },
+    });
+
+    const stream = await transport.reconnectToStream({
+      chatId: "chat-inactive-delete-onerror-failure",
+    });
+
+    expect(stream).toBeNull();
+  });
+
   it("supports custom payload mapping and trigger options resolver", async function () {
     let receivedTriggerBody: Record<string, unknown> | undefined;
     let receivedResolverChatId: string | undefined;
diff --git a/packages/ai/src/chatTransport.ts b/packages/ai/src/chatTransport.ts
index 5c6392852..9d5d3465d 100644
--- a/packages/ai/src/chatTransport.ts
+++ b/packages/ai/src/chatTransport.ts
@@ -258,7 +258,16 @@ export class TriggerChatTransport<
     }
 
     if (!runState.isActive) {
-      await this.runStore.delete(options.chatId);
+      try {
+        await this.runStore.delete(options.chatId);
+      } catch (error) {
+        await this.reportError({
+          phase: "reconnect",
+          chatId: runState.chatId,
+          runId: runState.runId,
+          error: normalizeError(error),
+        });
+      }
       return null;
     }