diff --git a/packages/xl-ai/src/AIExtension.test.ts b/packages/xl-ai/src/AIExtension.test.ts
new file mode 100644
index 0000000000..73e6dc3dff
--- /dev/null
+++ b/packages/xl-ai/src/AIExtension.test.ts
@@ -0,0 +1,144 @@
+/**
+ * Regression test for https://github.com/TypeCellOS/BlockNote/issues/3275
+ *
+ * `invokeAI` with the AI menu closed used to resolve on failure, because
+ * `setAIResponseStatus` drops updates while `aiMenuState` is `"closed"`.
+ */
+import { BlockNoteEditor } from "@blocknote/core";
+import { afterEach, describe, expect, it, vi } from "vite-plus/test";
+import { AIExtension } from "./AIExtension.js";
+
+const sendMessageWithAIRequest = vi.hoisted(() => vi.fn());
+
+vi.mock("./api/index.js", async (importOriginal) => {
+  const actual = await importOriginal<typeof import("./api/index.js")>();
+  return {
+    ...actual,
+    sendMessageWithAIRequest,
+  };
+});
+
+const mountedEditors: BlockNoteEditor[] = [];
+
+function createEditor() {
+  const editor = BlockNoteEditor.create({
+    initialContent: [
+      {
+        id: "paragraph-1",
+        type: "paragraph",
+        content: "Hello",
+      },
+    ],
+    extensions: [AIExtension()],
+  });
+  editor.mount(document.createElement("div"));
+  mountedEditors.push(editor);
+  return editor;
+}
+
+// jsdom does not implement scrolling. Opening the menu calls it on the block.
+function withScrollIntoView(run: () => void) {
+  const descriptor = Object.getOwnPropertyDescriptor(
+    HTMLElement.prototype,
+    "scrollIntoView",
+  );
+  Object.defineProperty(HTMLElement.prototype, "scrollIntoView", {
+    configurable: true,
+    value: () => {},
+  });
+  try {
+    run();
+  } finally {
+    if (descriptor) {
+      Object.defineProperty(
+        HTMLElement.prototype,
+        "scrollIntoView",
+        descriptor,
+      );
+    } else {
+      Reflect.deleteProperty(HTMLElement.prototype, "scrollIntoView");
+    }
+  }
+}
+
+afterEach(() => {
+  sendMessageWithAIRequest.mockReset();
+  while (mountedEditors.length > 0) {
+    mountedEditors.pop()?._tiptapEditor.destroy();
+  }
+});
+
+describe("invokeAI errors when the AI menu is closed", () => {
+  it("rejects with the chat error when the transport fails", async () => {
+    const error = new Error("HTTP 500");
+    sendMessageWithAIRequest.mockImplementation(async (chat: object) => {
+      Object.defineProperty(chat, "status", {
+        configurable: true,
+        get: () => "error",
+      });
+      Object.defineProperty(chat, "error", {
+        configurable: true,
+        get: () => error,
+      });
+      return { ok: true, value: undefined };
+    });
+    const ai = createEditor().getExtension(AIExtension)!;
+
+    await expect(ai.invokeAI({ userPrompt: "edit this" })).rejects.toBe(error);
+    expect(ai.store.state.aiMenuState).toBe("closed");
+  });
+
+  it("rejects with a tool-execution error", async () => {
+    const error = new Error("tool failed");
+    sendMessageWithAIRequest.mockResolvedValue({ ok: false, error });
+    const ai = createEditor().getExtension(AIExtension)!;
+
+    await expect(ai.invokeAI({ userPrompt: "edit this" })).rejects.toBe(error);
+    expect(ai.store.state.aiMenuState).toBe("closed");
+  });
+
+  it("rejects when the request throws", async () => {
+    const error = new Error("network down");
+    sendMessageWithAIRequest.mockRejectedValue(error);
+    const ai = createEditor().getExtension(AIExtension)!;
+
+    await expect(ai.invokeAI({ userPrompt: "edit this" })).rejects.toBe(error);
+    expect(ai.store.state.aiMenuState).toBe("closed");
+  });
+
+  it("records a failed result in the menu instead of rejecting when the menu is open", async () => {
+    const error = new Error("HTTP 500");
+    sendMessageWithAIRequest.mockResolvedValue({ ok: false, error });
+    const ai = createEditor().getExtension(AIExtension)!;
+    withScrollIntoView(() => {
+      ai.openAIMenuAtBlock("paragraph-1");
+    });
+
+    await expect(
+      ai.invokeAI({ userPrompt: "edit this" }),
+    ).resolves.toBeUndefined();
+    expect(ai.store.state.aiMenuState).toEqual({
+      status: "error",
+      error,
+      blockId: "paragraph-1",
+    });
+  });
+
+  it("records a thrown failure in the menu instead of rejecting when the menu is open", async () => {
+    const error = new Error("network down");
+    sendMessageWithAIRequest.mockRejectedValue(error);
+    const ai = createEditor().getExtension(AIExtension)!;
+    withScrollIntoView(() => {
+      ai.openAIMenuAtBlock("paragraph-1");
+    });
+
+    await expect(
+      ai.invokeAI({ userPrompt: "edit this" }),
+    ).resolves.toBeUndefined();
+    expect(ai.store.state.aiMenuState).toEqual({
+      status: "error",
+      error,
+      blockId: "paragraph-1",
+    });
+  });
+});
diff --git a/packages/xl-ai/src/AIExtension.ts b/packages/xl-ai/src/AIExtension.ts
index 7853ee8fd7..0b8ae07c7d 100644
--- a/packages/xl-ai/src/AIExtension.ts
+++ b/packages/xl-ai/src/AIExtension.ts
@@ -382,10 +382,26 @@ export const AIExtension = createExtension(
        * Execute a call to an LLM and apply the result to the editor
        */
       async invokeAI(opts: InvokeAIOptions) {
+        // Calls that start with the menu open keep today's behavior: the error
+        // is stored for the menu and the promise resolves. Programmatic calls
+        // leave the menu closed, and `setAIResponseStatus` drops that update,
+        // so reject instead — otherwise failure looks like success.
+        const invokedWhileMenuClosed = store.state.aiMenuState === "closed";
         this.setAIResponseStatus("thinking");
         // If in collaboration mode, fork the yDoc to allow modifications without affecting the remote
         editor.getExtension<typeof ForkYDocExtension>("yForkDoc")?.fork();
 
+        let closedMenuFailure: { error: unknown } | undefined;
+        const reportError = (error: unknown) => {
+          this.setAIResponseStatus({
+            status: "error",
+            error,
+          });
+          if (invokedWhileMenuClosed) {
+            closedMenuFailure = { error };
+          }
+        };
+
         try {
           // Create a new AbortController for this request
           const abortController = new AbortController();
@@ -505,16 +521,10 @@ export const AIExtension = createExtension(
               chatStatus: chat.status,
               chatError: chat.error,
             });
-            this.setAIResponseStatus({
-              status: "error",
-              error: result.ok ? chat.error : result.error,
-            });
+            reportError(result.ok ? chat.error : result.error);
           }
         } catch (e) {
-          this.setAIResponseStatus({
-            status: "error",
-            error: e,
-          });
+          reportError(e);
           // eslint-disable-next-line no-console
           console.error(
             "Unexpected error calling LLM",
@@ -522,6 +532,10 @@ export const AIExtension = createExtension(
             chatSession?.chat.messages,
           );
         }
+
+        if (closedMenuFailure) {
+          throw closedMenuFailure.error;
+        }
       },
     };
   },