diff --git a/packages/web/src/components/ui/__tests__/ContextMenuCheckbox.test.tsx b/packages/web/src/components/ui/__tests__/ContextMenuCheckbox.test.tsx
new file mode 100644
index 00000000..1fe57a02
--- /dev/null
+++ b/packages/web/src/components/ui/__tests__/ContextMenuCheckbox.test.tsx
@@ -0,0 +1,144 @@
+import { describe, it, expect, vi, beforeEach } from 'vitest';
+import { render, screen, act } from '@testing-library/react';
+import userEvent from '@testing-library/user-event';
+import { useContextMenuStore } from '../../../stores/contextMenuStore';
+import { ContextMenuRenderer } from '../ContextMenuRenderer';
+
+// Minimal mock for uiStore (ContextMenuRenderer reads isMobile)
+vi.mock('../../../stores/uiStore', () => ({
+  useUIStore: (selector: (s: { isMobile: boolean }) => unknown) =>
+    selector({ isMobile: false }),
+}));
+
+beforeEach(() => {
+  // Reset the context menu store to closed state between tests to prevent
+  // state leaking from one test into the next.
+  useContextMenuStore.getState().close();
+});
+
+describe('ContextMenu checkbox reactivity', () => {
+  it('updates checkbox indicator when store value changes on click', async () => {
+    const user = userEvent.setup();
+
+    // External state the checkbox subscribes to
+    let currentValue = false;
+    const listeners = new Set<() => void>();
+
+    const subscribe = (cb: () => void) => {
+      listeners.add(cb);
+      return () => listeners.delete(cb);
+    };
+    const getChecked = () => currentValue;
+    const onChange = (checked: boolean) => {
+      currentValue = checked;
+      listeners.forEach((cb) => cb());
+    };
+
+    // Open context menu with a reactive checkbox
+    useContextMenuStore.getState().open({ x: 100, y: 100 }, [
+      {
+        key: 'test-checkbox',
+        type: 'checkbox',
+        label: 'Test Mute',
+        subscribe,
+        getChecked,
+        onChange,
+      },
+    ]);
+
+    render(<ContextMenuRenderer />);
+
+    const button = screen.getByText('Test Mute').closest('button')!;
+    expect(button).toBeTruthy();
+
+    // Checkbox should start unchecked — the indicator's inner SVG checkmark should not be present
+    const getCheckmark = () => button.querySelector('svg[viewBox="0 0 24 24"]');
+    expect(getCheckmark()).toBeNull();
+
+    // Click to mute
+    await user.click(button);
+
+    // Checkbox should now be checked
+    expect(currentValue).toBe(true);
+    expect(getCheckmark()).not.toBeNull();
+
+    // Click again to unmute
+    await user.click(button);
+
+    // Checkbox should be unchecked again
+    expect(currentValue).toBe(false);
+    expect(getCheckmark()).toBeNull();
+  });
+
+  it('does not close the menu after toggling a checkbox', async () => {
+    const user = userEvent.setup();
+
+    let currentValue = false;
+    const listeners = new Set<() => void>();
+
+    useContextMenuStore.getState().open({ x: 100, y: 100 }, [
+      {
+        key: 'test-checkbox',
+        type: 'checkbox',
+        label: 'Stay Open',
+        subscribe: (cb: () => void) => {
+          listeners.add(cb);
+          return () => listeners.delete(cb);
+        },
+        getChecked: () => currentValue,
+        onChange: (checked: boolean) => {
+          currentValue = checked;
+          listeners.forEach((cb) => cb());
+        },
+      },
+    ]);
+
+    render(<ContextMenuRenderer />);
+
+    await user.click(screen.getByText('Stay Open'));
+
+    // Menu should still be open (item still visible)
+    expect(screen.getByText('Stay Open')).toBeTruthy();
+    expect(useContextMenuStore.getState().menu).not.toBeNull();
+  });
+
+  it('updates checkbox when external code changes the store (not via click)', async () => {
+    // External state the checkbox subscribes to
+    let currentValue = false;
+    const listeners = new Set<() => void>();
+
+    const subscribe = (cb: () => void) => {
+      listeners.add(cb);
+      return () => listeners.delete(cb);
+    };
+    const getChecked = () => currentValue;
+
+    useContextMenuStore.getState().open({ x: 100, y: 100 }, [
+      {
+        key: 'test-checkbox',
+        type: 'checkbox',
+        label: 'External Update',
+        subscribe,
+        getChecked,
+        onChange: () => {},
+      },
+    ]);
+
+    render(<ContextMenuRenderer />);
+
+    const button = screen.getByText('External Update').closest('button')!;
+    const getCheckmark = () => button.querySelector('svg[viewBox="0 0 24 24"]');
+
+    // Starts unchecked
+    expect(getCheckmark()).toBeNull();
+
+    // Simulate external store change (e.g., another component or WebSocket event)
+    act(() => {
+      currentValue = true;
+      listeners.forEach((cb) => cb());
+    });
+
+    // Checkbox should now show as checked without any click
+    expect(getCheckmark()).not.toBeNull();
+  });
+});