diff --git a/desktop/src/components/chat/AssistantOutputTargetCard.test.tsx b/desktop/src/components/chat/AssistantOutputTargetCard.test.tsx
index 2fd7b836..40e69906 100644
--- a/desktop/src/components/chat/AssistantOutputTargetCard.test.tsx
+++ b/desktop/src/components/chat/AssistantOutputTargetCard.test.tsx
@@ -107,4 +107,17 @@ describe('AssistantOutputTargetCard', () => {
     expect(await screen.findByText('openWith.inAppBrowser')).toBeInTheDocument()
     expect(screen.getByText('openWith.systemBrowser')).toBeInTheDocument()
   })
+
+  it('re-clicking the same open-with trigger TOGGLES the menu closed', async () => {
+    render(<AssistantOutputTargetCard target={localhostTarget} sessionId="s1" />)
+    const trigger = screen.getByLabelText('openWith.title')
+
+    // 1st click → opens
+    fireEvent.click(trigger)
+    expect(await screen.findByText('openWith.inAppBrowser')).toBeInTheDocument()
+
+    // 2nd click on the SAME trigger → closes (toggle)
+    fireEvent.click(trigger)
+    expect(screen.queryByText('openWith.inAppBrowser')).not.toBeInTheDocument()
+  })
 })
diff --git a/desktop/src/components/chat/AssistantOutputTargetCard.tsx b/desktop/src/components/chat/AssistantOutputTargetCard.tsx
index a627c232..8ddca096 100644
--- a/desktop/src/components/chat/AssistantOutputTargetCard.tsx
+++ b/desktop/src/components/chat/AssistantOutputTargetCard.tsx
@@ -21,7 +21,7 @@ type Props = {
 
 export function AssistantOutputTargetCard({ target, sessionId, workDir }: Props) {
   const t = useTranslation()
-  const [openWith, setOpenWith] = useState<{ items: OpenWithItem[]; anchor: DOMRect } | null>(null)
+  const [openWith, setOpenWith] = useState<{ items: OpenWithItem[]; anchor: DOMRect; triggerEl: HTMLElement } | null>(null)
 
   const isLocalhost = target.kind === 'localhost-url'
   const typeInfo = describeFileType(target.normalizedPath ?? target.href)
@@ -60,7 +60,15 @@ export function AssistantOutputTargetCard({ target, sessionId, workDir }: Props)
 
   const handleOpenWith = useCallback((event: ReactMouseEvent<HTMLButtonElement>) => {
     event.stopPropagation()
-    const rect = event.currentTarget.getBoundingClientRect()
+    // Toggle: a second click on the same trigger closes the menu. OpenWithMenu's
+    // outside-mousedown ignores the trigger, so the trigger's own click is the
+    // only path that can close it on re-click.
+    if (openWith) {
+      setOpenWith(null)
+      return
+    }
+    const triggerEl = event.currentTarget
+    const rect = triggerEl.getBoundingClientRect()
     void (async () => {
       await useOpenTargetStore.getState().ensureTargets()
       const targets = useOpenTargetStore.getState().targets
@@ -77,9 +85,9 @@ export function AssistantOutputTargetCard({ target, sessionId, workDir }: Props)
         openTarget: (id, abs) => { void useOpenTargetStore.getState().openTarget(id, abs) },
         t: (k, v) => t(k as TranslationKey, v),
       })
-      setOpenWith({ items, anchor: rect })
+      setOpenWith({ items, anchor: rect, triggerEl })
     })()
-  }, [sessionId, t, target.href, workDir])
+  }, [openWith, sessionId, t, target.href, workDir])
 
   return (
     <section className="flex items-start gap-3 rounded-[var(--radius-lg)] border border-[var(--color-border)]/70 bg-[var(--color-surface-container-low)] px-3 py-2.5 shadow-sm">
@@ -137,7 +145,7 @@ export function AssistantOutputTargetCard({ target, sessionId, workDir }: Props)
         </button>
       </div>
 
-      {openWith && <OpenWithMenu items={openWith.items} anchor={openWith.anchor} onClose={() => setOpenWith(null)} />}
+      {openWith && <OpenWithMenu items={openWith.items} anchor={openWith.anchor} triggerEl={openWith.triggerEl} onClose={() => setOpenWith(null)} />}
     </section>
   )
 }
diff --git a/desktop/src/components/chat/CurrentTurnChangeCard.tsx b/desktop/src/components/chat/CurrentTurnChangeCard.tsx
index 5f4722db..27d29460 100644
--- a/desktop/src/components/chat/CurrentTurnChangeCard.tsx
+++ b/desktop/src/components/chat/CurrentTurnChangeCard.tsx
@@ -38,7 +38,7 @@ export function CurrentTurnChangeCard({
   onUndo,
 }: CurrentTurnChangeCardProps) {
   const t = useTranslation()
-  const [openWith, setOpenWith] = useState<{ items: OpenWithItem[]; anchor: DOMRect } | null>(null)
+  const [openWith, setOpenWith] = useState<{ items: OpenWithItem[]; anchor: DOMRect; triggerEl: HTMLElement } | null>(null)
   const [showAllFiles, setShowAllFiles] = useState(false)
 
   const files = useMemo<ChangedFileEntry[]>(
@@ -63,7 +63,15 @@ export function CurrentTurnChangeCard({
 
   const handleOpenWith = useCallback((event: ReactMouseEvent<HTMLButtonElement>, fileEntry: ChangedFileEntry) => {
     event.stopPropagation()
-    const rect = event.currentTarget.getBoundingClientRect()
+    // Toggle: if the menu is already open, a second click on the trigger closes it
+    // (the OpenWithMenu's outside-mousedown handler excludes the trigger, so its
+    //  own click is the only thing that can close it on re-click).
+    if (openWith) {
+      setOpenWith(null)
+      return
+    }
+    const triggerEl = event.currentTarget
+    const rect = triggerEl.getBoundingClientRect()
     void (async () => {
       await useOpenTargetStore.getState().ensureTargets()
       const targets = useOpenTargetStore.getState().targets
@@ -78,9 +86,9 @@ export function CurrentTurnChangeCard({
         openTarget: (id, abs) => { void useOpenTargetStore.getState().openTarget(id, abs) },
         t: (k, v) => t(k as TranslationKey, v),
       })
-      setOpenWith({ items, anchor: rect })
+      setOpenWith({ items, anchor: rect, triggerEl })
     })()
-  }, [sessionId, t])
+  }, [openWith, sessionId, t])
 
   const cardLabel = isLatest
     ? t('chat.turnChangesLatestCardLabel')
@@ -193,7 +201,7 @@ export function CurrentTurnChangeCard({
         </div>
       )}
 
-      {openWith && <OpenWithMenu items={openWith.items} anchor={openWith.anchor} onClose={() => setOpenWith(null)} />}
+      {openWith && <OpenWithMenu items={openWith.items} anchor={openWith.anchor} triggerEl={openWith.triggerEl} onClose={() => setOpenWith(null)} />}
     </section>
   )
 }
diff --git a/desktop/src/components/common/OpenWithMenu.test.tsx b/desktop/src/components/common/OpenWithMenu.test.tsx
index 27cb52d1..a2481163 100644
--- a/desktop/src/components/common/OpenWithMenu.test.tsx
+++ b/desktop/src/components/common/OpenWithMenu.test.tsx
@@ -69,6 +69,65 @@ describe('OpenWithMenu', () => {
     expect(onClose).toHaveBeenCalledTimes(1)
   })
 
+  describe('triggerEl exclusion (re-click-trigger toggle support)', () => {
+    it('does NOT call onClose when mousedown lands inside triggerEl', () => {
+      // Set up a trigger element + a child within it in the document.
+      const trigger = document.createElement('button')
+      const triggerChild = document.createElement('span')
+      trigger.appendChild(triggerChild)
+      document.body.appendChild(trigger)
+      const onClose = vi.fn()
+      render(<OpenWithMenu items={makeItems()} anchor={anchor} onClose={onClose} triggerEl={trigger} />)
+
+      // mousedown on the trigger itself
+      fireEvent.mouseDown(trigger)
+      expect(onClose).not.toHaveBeenCalled()
+
+      // mousedown on a descendant of the trigger
+      fireEvent.mouseDown(triggerChild)
+      expect(onClose).not.toHaveBeenCalled()
+
+      document.body.removeChild(trigger)
+    })
+
+    it('STILL calls onClose for true outside clicks (not menu, not trigger)', () => {
+      const trigger = document.createElement('button')
+      document.body.appendChild(trigger)
+      const outside = document.createElement('div')
+      document.body.appendChild(outside)
+      const onClose = vi.fn()
+      render(<OpenWithMenu items={makeItems()} anchor={anchor} onClose={onClose} triggerEl={trigger} />)
+
+      fireEvent.mouseDown(outside)
+      expect(onClose).toHaveBeenCalledTimes(1)
+
+      document.body.removeChild(trigger)
+      document.body.removeChild(outside)
+    })
+
+    it('Escape still closes when triggerEl is provided', () => {
+      const trigger = document.createElement('button')
+      document.body.appendChild(trigger)
+      const onClose = vi.fn()
+      render(<OpenWithMenu items={makeItems()} anchor={anchor} onClose={onClose} triggerEl={trigger} />)
+      fireEvent.keyDown(document, { key: 'Escape' })
+      expect(onClose).toHaveBeenCalledTimes(1)
+      document.body.removeChild(trigger)
+    })
+
+    it('item click still closes the menu when triggerEl is provided', () => {
+      const trigger = document.createElement('button')
+      document.body.appendChild(trigger)
+      const onClose = vi.fn()
+      const onSelect1 = vi.fn()
+      render(<OpenWithMenu items={makeItems(onSelect1)} anchor={anchor} onClose={onClose} triggerEl={trigger} />)
+      fireEvent.click(screen.getByText('In-app browser'))
+      expect(onSelect1).toHaveBeenCalledTimes(1)
+      expect(onClose).toHaveBeenCalledTimes(1)
+      document.body.removeChild(trigger)
+    })
+  })
+
   it('flips above the anchor when it would overflow the viewport bottom', () => {
     // The trigger often sits right above the composer; the menu must not render off-screen below it.
     Object.defineProperty(window, 'innerHeight', { value: 300, configurable: true })
diff --git a/desktop/src/components/common/OpenWithMenu.tsx b/desktop/src/components/common/OpenWithMenu.tsx
index 11a2e9cb..ae1f75de 100644
--- a/desktop/src/components/common/OpenWithMenu.tsx
+++ b/desktop/src/components/common/OpenWithMenu.tsx
@@ -8,6 +8,10 @@ type Props = {
   items: OpenWithItem[]
   anchor: { top: number; bottom: number; left: number; right: number }
   onClose: () => void
+  // Optional trigger element to exclude from outside-close detection. When the
+  // user clicks the same trigger that opened this menu, the trigger's own
+  // click handler is responsible for toggling — don't double-close here.
+  triggerEl?: HTMLElement | null
 }
 
 function ItemIcon({ item }: { item: OpenWithItem }) {
@@ -19,7 +23,7 @@ function ItemIcon({ item }: { item: OpenWithItem }) {
 
 const MARGIN = 8
 
-export function OpenWithMenu({ items, anchor, onClose }: Props) {
+export function OpenWithMenu({ items, anchor, onClose, triggerEl }: Props) {
   const ref = useRef<HTMLDivElement>(null)
   // Initial guess; corrected (before paint) by the layout effect once we can measure the menu.
   const [pos, setPos] = useState<{ top: number; left: number }>(() => ({
@@ -47,12 +51,20 @@ export function OpenWithMenu({ items, anchor, onClose }: Props) {
   }, [anchor])
 
   useEffect(() => {
-    const onDown = (e: MouseEvent) => { if (!ref.current?.contains(e.target as Node)) onClose() }
+    const onDown = (e: MouseEvent) => {
+      const target = e.target as Node | null
+      if (!target) return
+      // Ignore clicks inside the menu itself, AND clicks inside the trigger
+      // element that opened it — the trigger's own onClick handler will toggle.
+      if (ref.current?.contains(target)) return
+      if (triggerEl && triggerEl.contains(target)) return
+      onClose()
+    }
     const onKey = (e: KeyboardEvent) => { if (e.key === 'Escape') onClose() }
     document.addEventListener('mousedown', onDown)
     document.addEventListener('keydown', onKey)
     return () => { document.removeEventListener('mousedown', onDown); document.removeEventListener('keydown', onKey) }
-  }, [onClose])
+  }, [onClose, triggerEl])
 
   return createPortal(
     <div