diff --git a/src/server/connection-routes.ts b/src/server/connection-routes.ts
index fd0d550d..d15669de 100644
--- a/src/server/connection-routes.ts
+++ b/src/server/connection-routes.ts
@@ -132,6 +132,15 @@ export function connectionRoutes(
     const earlier = recovered();
     if (earlier) return earlier;
     const { approval, exposed } = approvalFor(thread.id, body.approvalId);
+    // An approval runs its stored request once. The claim below binds one
+    // tool call id, so without this check the same approval could execute
+    // again for every fresh tool call id sent with it.
+    const claimed = connections.store.actionForApproval(approval.id);
+    if (claimed && claimed.toolCallId !== body.toolCallId)
+      return c.json(
+        { error: 'This approval request already ran its stored action.' },
+        409,
+      );
     if (
       !connections.store.claimAction(
         thread.id,
diff --git a/src/server/connection-store.ts b/src/server/connection-store.ts
index bc53c1b7..2fc3908d 100644
--- a/src/server/connection-store.ts
+++ b/src/server/connection-store.ts
@@ -153,6 +153,18 @@ export class ConnectionStore {
           : null,
     };
   }
+  // Looks up what an approval was already claimed for, so one approval can
+  // never run its stored request twice under different tool call ids.
+  actionForApproval(approvalId: string) {
+    const row = this.db
+      .prepare(
+        'SELECT threadId, toolCallId FROM mcp_actions WHERE approvalId=?',
+      )
+      .get(approvalId);
+    return row
+      ? { threadId: String(row.threadId), toolCallId: String(row.toolCallId) }
+      : undefined;
+  }
   // Claim an approved action once. Returns false if it was already claimed,
   // so a double click or a retried request never executes twice.
   claimAction(
diff --git a/tests/connections.test.ts b/tests/connections.test.ts
index 80332791..f07cb0e2 100644
--- a/tests/connections.test.ts
+++ b/tests/connections.test.ts
@@ -486,3 +486,31 @@ it('returns a saved result only for the approval that produced it', async () =>
   expect(sent).toHaveBeenCalledOnce();
   expect(sent.mock.calls[0][0]).toMatchObject({ to: 'alice@example.com' });
 });
+
+it('runs an approved request once, even under a fresh toolCallId', async () => {
+  const { dot, connections, request, sent } = fixture();
+  await connections.add(dot.id, {
+    name: 'Mail',
+    url: 'https://mail.example.com/mcp',
+  });
+  const approvalId = await requestApproval(
+    connections,
+    dot.id,
+    'mail__send_mail',
+    { to: 'a@example.com', body: 'Hi' },
+  );
+  const approve = (toolCallId: string) =>
+    request('/conversations/thread/connection-actions', 'POST', {
+      toolCallId,
+      approvalId,
+    });
+  expect(await (await approve('tc1')).json()).toEqual({
+    isError: false,
+    text: 'Sent to a@example.com',
+  });
+  // The stored request ran. The same approval must not run it a second
+  // time under a different tool call id.
+  const replay = await approve('tc2');
+  expect(replay.status).toBe(409);
+  expect(sent).toHaveBeenCalledOnce();
+});