diff --git a/src/infra/approval-handler-runtime.test.ts b/src/infra/approval-handler-runtime.test.ts
index 9d6922866d26..61ecdb1a1383 100644
--- a/src/infra/approval-handler-runtime.test.ts
+++ b/src/infra/approval-handler-runtime.test.ts
@@ -364,4 +364,44 @@ describe("createLazyChannelApprovalNativeRuntimeAdapter", () => {
     expect(onDelivered).toHaveBeenCalledWith({ request: { id: "exec:1" } });
     expect(load).toHaveBeenCalledTimes(1);
   });
+
+  it("unbinds in-flight wrapped entry when stop() fires between deliverPending and bindPending", async () => {
+    const deliverGate = { resolve: () => {}, promise: Promise.resolve() };
+    const deliverPromise = new Promise<void>((resolve) => {
+      deliverGate.resolve = resolve;
+    });
+    deliverGate.promise = deliverPromise;
+    const deliverPending = vi.fn(async () => {
+      await deliverPromise;
+      return { messageId: "in-flight" };
+    });
+    const bindPending = vi.fn().mockResolvedValue({ bindingId: "bound-in-flight" });
+    const unbindPending = vi.fn();
+
+    const runtime = await createTestApprovalHandler(
+      makeNativeApprovalCapability({
+        deliverPending,
+        bindPending,
+        unbindPending,
+      }),
+    );
+    const approvalRuntime = expectApprovalRuntime(runtime);
+    const request = makeExecApprovalRequest("exec:in-flight");
+
+    const inflight = approvalRuntime.handleRequested(request);
+    await new Promise((r) => setTimeout(r, 0));
+
+    // stop() while deliverPending is parked — onStopped flips the closure flag.
+    await approvalRuntime.stop();
+    deliverGate.resolve();
+    await inflight;
+
+    expect(unbindPending).toHaveBeenCalledTimes(1);
+    const unbind = firstCallArg(unbindPending) as
+      | { entry?: unknown; binding?: unknown; request?: unknown }
+      | undefined;
+    expect(unbind?.entry).toEqual({ messageId: "in-flight" });
+    expect(unbind?.request).toBe(request);
+    expect(bindPending).not.toHaveBeenCalled();
+  });
 });
diff --git a/src/infra/approval-handler-runtime.ts b/src/infra/approval-handler-runtime.ts
index 494d70c907b1..bd3ddb975f4b 100644
--- a/src/infra/approval-handler-runtime.ts
+++ b/src/infra/approval-handler-runtime.ts
@@ -442,6 +442,7 @@ export async function createChannelApprovalHandlerFromCapability(params: {
   }
   const log = createSubsystemLogger(params.label);
   const activeEntries = new Map<string, ActiveApprovalEntries>();
+  let stopped = false;
   const resolveApprovalKind =
     nativeRuntime.resolveApprovalKind ??
     ((request: ApprovalRequest) =>
@@ -514,6 +515,15 @@ export async function createChannelApprovalHandlerFromCapability(params: {
         if (!entry) {
           return null;
         }
+        if (stopped) {
+          await nativeRuntime.interactions?.unbindPending?.({
+            ...baseContext,
+            entry,
+            request,
+            approvalKind,
+          });
+          return null;
+        }
         const binding = await nativeRuntime.interactions?.bindPending?.({
           ...baseContext,
           entry,
@@ -522,6 +532,16 @@ export async function createChannelApprovalHandlerFromCapability(params: {
           view: pendingContent.view,
           pendingPayload: pendingContent.payload,
         });
+        if (stopped) {
+          await nativeRuntime.interactions?.unbindPending?.({
+            ...baseContext,
+            entry,
+            ...(binding === undefined || binding === null ? {} : { binding }),
+            request,
+            approvalKind,
+          });
+          return null;
+        }
         const wrapped: WrappedPendingEntry = {
           entry,
           ...(binding === undefined || binding === null ? {} : { binding }),
@@ -654,6 +674,7 @@ export async function createChannelApprovalHandlerFromCapability(params: {
         });
       },
       onStopped: async () => {
+        stopped = true;
         if (activeEntries.size === 0) {
           activeEntries.clear();
           return;