@@ -193,7 +193,7 @@ async function render(
   requestMode: 'agent' | 'assistant' = 'assistant',
   controls: Pick<
     ComponentProps<typeof Composer>,
-    'isSending' | 'showModeSelector' | 'onModeChange' | 'restoredContexts'
+    'isSending' | 'showModeSelector' | 'onModeChange' | 'restoredContexts' | 'onSendQueuedHead'
   > = { isSending: false }
 ) {
   function Harness() {
@@ -215,6 +215,7 @@ async function render(
         isInitialView={isInitialView}
         isSending={controls.isSending}
         onStop={vi.fn()}
+        onSendQueuedHead={controls.onSendQueuedHead}
         onSubmit={(text, contexts) => {
           mocks.submit(text, files.attachedFiles)
           mocks.contexts(contexts)
@@ -919,3 +920,42 @@ it('offers the advanced models and each model’s supported efforts', async () =
     )
   ).toEqual(['Low', 'Medium', 'High', 'Extra High', 'Max'])
 })
+
+it.each([
+  ['agent', false],
+  ['assistant', false],
+  ['agent', true],
+  ['assistant', true],
+] as const)(
+  'queues once then sends immediately on rapid double Enter (%s, attachment: %s)',
+  async (mode, withAttachment) => {
+    const sendHead = vi.fn()
+    await render(false, withAttachment ? '' : 'Use the latest report', mode, {
+      isSending: true,
+      onSendQueuedHead: sendHead,
+    })
+    if (withAttachment) await paste([new File(['image'], 'follow-up.png', { type: 'image/png' })])
+    const input = container.querySelector<HTMLTextAreaElement>('[aria-label="Ask Sim"]')!
+    await act(async () => {
+      input.dispatchEvent(new KeyboardEvent('keydown', { key: 'Enter', bubbles: true }))
+      expect(mocks.submit).toHaveBeenCalledTimes(1)
+      expect(sendHead).not.toHaveBeenCalled()
+      input.dispatchEvent(new KeyboardEvent('keydown', { key: 'Enter', bubbles: true }))
+    })
+    expect(mocks.submit).toHaveBeenCalledTimes(1)
+    expect(sendHead).toHaveBeenCalledExactlyOnceWith()
+    expect(input.value).toBe('')
+  }
+)
+
+it('does not send a queued head on empty Enter when idle', async () => {
+  const sendHead = vi.fn()
+  await render(false, '', 'assistant', { isSending: false, onSendQueuedHead: sendHead })
+  await act(async () => {
+    container
+      .querySelector<HTMLTextAreaElement>('[aria-label="Ask Sim"]')!
+      .dispatchEvent(new KeyboardEvent('keydown', { key: 'Enter', bubbles: true }))
+  })
+  expect(sendHead).not.toHaveBeenCalled()
+  expect(mocks.submit).not.toHaveBeenCalled()
+})
@@ -46,6 +46,7 @@ interface ComposerProps {
   onChange: (value: string, contexts?: ChatContext[]) => void
   restoredContexts?: ChatContext[]
   onSubmit: (text: string, contexts?: ChatContext[]) => void
+  onSendQueuedHead?: () => void
   onStop: () => void
 }
 
@@ -65,9 +66,12 @@ export function Composer({
   isSending,
   onChange,
   onSubmit,
+  onSendQueuedHead,
   restoredContexts,
   onStop,
 }: ComposerProps) {
+  const attachedFilesRef = useRef(files.attachedFiles)
+  attachedFilesRef.current = files.attachedFiles
   const imagesOnly = requestMode === 'assistant'
   const { organization } = useOrganizationContext()
   const { data: allWorkspaces = [] } = useWorkspacesQuery(!imagesOnly)
@@ -147,7 +151,15 @@ export function Composer({
   const placeholder = isInitialView ? animatedPlaceholder : 'Send message to Sim'
 
   const submit = () => {
-    if (!canSubmit) return
+    if (attachedFilesRef.current.some((file) => file.uploading)) return
+    const hasPayload =
+      editor.getValue().trim().length > 0 || attachedFilesRef.current.some((file) => file.key)
+    if (!hasPayload) {
+      if (isSending) onSendQueuedHead?.()
+      return
+    }
+    /** Consume attachments synchronously so a second Enter cannot submit them twice. */
+    attachedFilesRef.current = []
     voice.resetTranscript()
     const contexts = imagesOnly ? [] : editor.getActiveContexts()
     onSubmit(editor.getPlainValue(), contexts.length ? contexts : undefined)
 
@@ -1013,3 +1013,17 @@ it('keeps an attachment-only draft across remounts and clears it when its last f
   ).toBeUndefined()
   expect(composerProps().files.attachedFiles).toEqual([])
 })
+
+it('wires empty Enter to the live queue sender for an active organization chat', async () => {
+  const sendNow = vi.fn()
+  mocks.chat.mockReturnValue({
+    ...mocks.chat(),
+    messages: [{ id: 'user-1', role: 'user', content: 'First message' }],
+    isSending: true,
+    sendNow,
+  })
+  mocks.renderer.mockImplementation(({ composer }: { composer: ReactNode }) => composer)
+  await act(async () => renderHome(<OrganizationHome chatId='chat-a' />))
+  await act(async () => composerProps().onSendQueuedHead?.())
+  expect(sendNow).toHaveBeenCalledExactlyOnceWith()
+})
@@ -315,6 +315,9 @@ function OrganizationHomeContent({
         isSending={chat.isSending || chat.isReconnecting}
         onChange={setDraft}
         onSubmit={submit}
+        onSendQueuedHead={() => {
+          void chat.sendNow()
+        }}
         onStop={() => {
           void chat.stopGeneration()
         }}
 
@@ -6,9 +6,10 @@ import { createRoot } from 'react-dom/client'
 import { expect, it, vi } from 'vitest'
 import type { ChatMessage } from '@/app/workspace/[workspaceId]/home/types'
 
-const { scrollToIndex, renderMessage } = vi.hoisted(() => ({
+const { scrollToIndex, renderMessage, renderInput } = vi.hoisted(() => ({
   scrollToIndex: vi.fn(),
   renderMessage: vi.fn(),
+  renderInput: vi.fn(),
 }))
 
 /** The measured range still covers the old turn while appended rows await measurement. */
@@ -39,7 +40,10 @@ vi.mock('@tanstack/react-virtual', async (importOriginal) => {
 })
 vi.mock('@/app/workspace/[workspaceId]/components', () => ({ MessageActions: () => null }))
 vi.mock('@/app/workspace/[workspaceId]/home/components/user-input', () => ({
-  UserInput: () => null,
+  UserInput: (props: { onSendQueuedHead: () => void }) => {
+    renderInput(props)
+    return null
+  },
 }))
 vi.mock('@/app/workspace/[workspaceId]/home/components/queued-messages', () => ({
   QueuedMessages: () => null,
@@ -231,3 +235,45 @@ it('never restarts the previous response while a new send waits for its deferred
     vi.unstubAllGlobals()
   }
 })
+
+it('delegates empty Enter to the live queue sender before the rendered queue updates', async () => {
+  vi.stubGlobal('IS_REACT_ACT_ENVIRONMENT', true)
+  vi.stubGlobal(
+    'ResizeObserver',
+    class {
+      observe() {}
+      disconnect() {}
+    }
+  )
+  const container = document.createElement('div')
+  const root = createRoot(container)
+  const client = new QueryClient()
+  const sendNow = vi.fn().mockResolvedValue(undefined)
+  try {
+    await act(async () =>
+      root.render(
+        <QueryClientProvider client={client}>
+          <MothershipChat
+            messages={[]}
+            isSending
+            messageQueue={[]}
+            onSubmit={vi.fn()}
+            onStopGeneration={vi.fn()}
+            onSendQueuedMessage={sendNow}
+            editingQueuedId={null}
+            dispatchingHeadId={null}
+            onRemoveQueuedMessage={vi.fn()}
+            onEditQueuedMessage={vi.fn()}
+            onCancelQueueEdit={vi.fn()}
+          />
+        </QueryClientProvider>
+      )
+    )
+    await act(async () => renderInput.mock.lastCall![0].onSendQueuedHead())
+    expect(sendNow).toHaveBeenCalledExactlyOnceWith()
+  } finally {
+    await act(async () => root.unmount())
+    client.clear()
+    vi.unstubAllGlobals()
+  }
+})
@@ -80,7 +80,7 @@ interface MothershipChatProps {
   editingQueuedId: string | null
   dispatchingHeadId: string | null
   onRemoveQueuedMessage: (id: string) => void
-  onSendQueuedMessage: (id: string) => Promise<void>
+  onSendQueuedMessage: (id?: string) => Promise<void>
   onEditQueuedMessage: (id: string) => QueuedMessage | undefined
   onCancelQueueEdit: () => void
   userId?: string
@@ -722,9 +722,8 @@ export function MothershipChat({
   }, [])
 
   const handleSendQueuedHead = useCallback(() => {
-    const topMessage = messageQueueRef.current[0]
-    if (!topMessage) return
-    void onSendQueuedMessage(topMessage.id)
+    /** The first Enter can enqueue before this component has rendered the new queue. */
+    void onSendQueuedMessage()
   }, [onSendQueuedMessage])
 
   const handleEditQueued = useCallback(
 
@@ -68,15 +68,18 @@ vi.mock('@/app/workspace/[workspaceId]/home/components/user-input/components', a
     PromptEditor: ({
       editor,
       placeholder,
+      onSubmit,
     }: {
       editor: PromptEditorInstance
       placeholder: string
+      onSubmit: () => void
     }) => (
       <textarea
         ref={editor.textareaRef}
         value={editor.value}
         placeholder={placeholder}
         onChange={editor.handleInputChange}
+        onKeyDown={(event) => editor.handleKeyDown(event, { onSubmit })}
       />
     ),
     SendButton: ({ onSubmit }: { onSubmit: () => void }) => (
@@ -109,7 +112,7 @@ const QUEUED_MESSAGE: QueuedMessage = {
 let root: Root | null = null
 let container: HTMLDivElement | null = null
 
-function mount() {
+function mount(isSending = false, onSendQueuedHead?: () => void) {
   const inputRef = createRef<UserInputHandle>()
 
   function Composer() {
@@ -127,7 +130,8 @@ function mount() {
           ref={inputRef}
           defaultValue='Initial draft'
           onSubmit={mockSubmit}
-          isSending={false}
+          isSending={isSending}
+          onSendQueuedHead={onSendQueuedHead}
           onStopGeneration={vi.fn()}
         />
       </>
@@ -218,3 +222,19 @@ describe('workspace composer', () => {
     expect(mockResetTranscript).toHaveBeenCalled()
   })
 })
+
+it.each([false, true])(
+  'sends a queued message on the second Enter without resubmitting attachments (%s)',
+  async (withAttachment) => {
+    const sendHead = vi.fn()
+    mount(true, sendHead)
+    if (withAttachment) await clickButton('Edit queued')
+    await act(async () => {
+      textarea().dispatchEvent(new KeyboardEvent('keydown', { key: 'Enter', bubbles: true }))
+      textarea().dispatchEvent(new KeyboardEvent('keydown', { key: 'Enter', bubbles: true }))
+    })
+    expect(mockSubmit).toHaveBeenCalledTimes(1)
+    expect(sendHead).toHaveBeenCalledExactlyOnceWith()
+    expect(textarea().value).toBe('')
+  }
+)
@@ -476,6 +476,7 @@ const UserInputImpl = forwardRef<UserInputHandle, UserInputProps>(function UserI
     prevSelectedContextsRef.current = []
     resetTranscript()
     filesRef.current.clearAttachedFiles()
+    filesRef.current = { ...filesRef.current, attachedFiles: [] }
   }, [resetTranscript])
 
   const handleSubmit = useCallback(() => {
 
@@ -1450,6 +1450,46 @@ describe('useChat remount send recovery', () => {
     }
   )
 
+  it('sends the live queue head once without waiting for a render, after Stop settles', async () => {
+    state.postBehavior = 'task'
+    const { getResult } = renderUseChatInChat('chat-a')
+    await act(async () => {
+      void getResult().sendMessage('Original request')
+    })
+    await waitFor(() => state.postBodies.length === 1 && getResult().isSending)
+    let releaseStop = () => {}
+    const stopGate = new Promise<void>((resolve) => {
+      releaseStop = resolve
+    })
+    let stopRequested = false
+    vi.stubGlobal('fetch', async (input: RequestInfo | URL, init?: RequestInit) => {
+      if (String(input).includes('/api/copilot/chat/abort')) {
+        stopRequested = true
+        await stopGate
+      }
+      return fetchStub(input, init)
+    })
+    state.postBehavior = 'hang'
+    const beforeRender = getResult()
+    await act(async () => {
+      void beforeRender.sendMessage('Use the latest report')
+      void beforeRender.sendNow()
+      void beforeRender.sendNow()
+    })
+    try {
+      await waitFor(() => stopRequested)
+      expect(state.postBodies).toHaveLength(1)
+    } finally {
+      await act(async () => {
+        releaseStop()
+      })
+    }
+    await waitFor(() => state.postBodies.length === 2)
+    expect(state.postBodies[1].message).toBe('Use the latest report')
+    expect(allQueuedMessages()).toHaveLength(0)
+    expect(state.abortBodies).toHaveLength(1)
+  })
+
   it('captures Search levels independently for each queued turn and omits it from Build requests', async () => {
     state.postBehavior = 'task'
     const { getResult } = renderUseChat({ organizationId: 'org-a' }, 'assistant')
 
@@ -271,7 +271,7 @@ export interface UseChatReturn {
   reorderResources: (resources: MothershipResource[]) => void
   messageQueue: QueuedMessage[]
   removeFromQueue: (id: string) => void
-  sendNow: (id: string) => Promise<void>
+  sendNow: (id?: string) => Promise<void>
   editQueuedMessage: (id: string) => QueuedMessage | undefined
   cancelQueueEdit: () => void
   editingQueuedId: string | null
@@ -4784,9 +4784,9 @@ export function useChat(
   }, [])
 
   const sendQueuedMessageImmediately = useCallback(
-    async (id: string) => {
+    async (id?: string) => {
       const queue = useMothershipQueueStore.getState().queues[chatKeyRef.current]
-      const msg = queue?.find((queued) => queued.id === id)
+      const msg = id === undefined ? queue?.[0] : queue?.find((queued) => queued.id === id)
       if (!msg) return
       if (queuedMessageDispatchIdsRef.current.has(msg.id)) return
       const admissionPending = hasPendingChatAdmission()
@@ -4844,7 +4844,7 @@ export function useChat(
   )
 
   const sendNow = useCallback(
-    async (id: string) => {
+    async (id?: string) => {
       await sendQueuedMessageImmediately(id)
     },
     [sendQueuedMessageImmediately]