diff --git a/desktop/src/components/chat/AskUserQuestion.test.tsx b/desktop/src/components/chat/AskUserQuestion.test.tsx
index 0e4171e1..4e5b030d 100644
--- a/desktop/src/components/chat/AskUserQuestion.test.tsx
+++ b/desktop/src/components/chat/AskUserQuestion.test.tsx
@@ -296,12 +296,12 @@ describe('AskUserQuestion', () => {
     })
     fireEvent.click(screen.getByRole('button', { name: /Q2$/ }))
 
-    expect((screen.getByPlaceholderText('Type your answer...') as HTMLInputElement).value).toBe('')
+    expect((screen.getByPlaceholderText('Type your answer...') as HTMLTextAreaElement).value).toBe('')
 
     fireEvent.click(screen.getByRole('button', { name: /^A2$/ }))
     fireEvent.click(screen.getByRole('button', { name: /Q1$/ }))
 
-    expect((screen.getByPlaceholderText('Type your answer...') as HTMLInputElement).value).toBe('custom-q1')
+    expect((screen.getByPlaceholderText('Type your answer...') as HTMLTextAreaElement).value).toBe('custom-q1')
 
     fireEvent.click(screen.getByRole('button', { name: /submit/i }))
 
@@ -318,4 +318,49 @@ describe('AskUserQuestion', () => {
       },
     })
   })
+
+  it('uses a multiline custom response box and submits it with Ctrl+Enter', () => {
+    render(
+      <AskUserQuestion
+        toolUseId="tool-1"
+        input={{
+          questions: [
+            {
+              question: 'What context should we restore?',
+              options: [{ label: 'Skip' }],
+            },
+          ],
+        }}
+      />,
+    )
+
+    const textarea = screen.getByPlaceholderText('Type your answer...')
+    expect(textarea.tagName).toBe('TEXTAREA')
+    expect(textarea.getAttribute('rows')).toBe('3')
+
+    fireEvent.change(textarea, {
+      target: { value: 'First restored context line\nSecond restored context line' },
+    })
+    fireEvent.keyDown(textarea, { key: 'Enter' })
+    expect(sendMock).not.toHaveBeenCalled()
+
+    fireEvent.keyDown(textarea, { key: 'Enter', ctrlKey: true })
+
+    expect(sendMock).toHaveBeenCalledWith(ACTIVE_TAB, {
+      type: 'permission_response',
+      requestId: 'perm-1',
+      allowed: true,
+      updatedInput: {
+        questions: [
+          {
+            question: 'What context should we restore?',
+            options: [{ label: 'Skip' }],
+          },
+        ],
+        answers: {
+          'What context should we restore?': 'First restored context line\nSecond restored context line',
+        },
+      },
+    })
+  })
 })
diff --git a/desktop/src/components/chat/AskUserQuestion.tsx b/desktop/src/components/chat/AskUserQuestion.tsx
index ecd71cc8..e7acbcc9 100644
--- a/desktop/src/components/chat/AskUserQuestion.tsx
+++ b/desktop/src/components/chat/AskUserQuestion.tsx
@@ -320,18 +320,22 @@ export function AskUserQuestion({ sessionId, toolUseId, input, result }: Props)
             <label className="text-xs text-[var(--color-text-tertiary)] mb-1.5 block">
               {t('question.customResponse')}
             </label>
-            <input
-              type="text"
+            <textarea
               value={freeTexts[safeActiveTab] ?? ''}
               onChange={(e) => handleFreeTextChange(safeActiveTab, e.target.value)}
               onCompositionStart={() => { composingRef.current = true }}
               onCompositionEnd={() => { composingRef.current = false }}
               onKeyDown={(e) => {
                 if (composingRef.current || e.nativeEvent.isComposing || e.keyCode === 229) return
-                if (e.key === 'Enter' && allAnswered) handleSubmit()
+                if (e.key === 'Enter' && (e.ctrlKey || e.metaKey) && allAnswered) {
+                  e.preventDefault()
+                  handleSubmit()
+                }
               }}
               placeholder={t('question.typePlaceholder')}
-              className="w-full px-3 py-2 text-sm bg-[var(--color-surface)] border border-[var(--color-outline-variant)]/40 rounded-[var(--radius-md)] text-[var(--color-text-primary)] placeholder:text-[var(--color-text-tertiary)] focus:outline-none focus:border-[var(--color-secondary)] focus:ring-1 focus:ring-[var(--color-secondary)]/30"
+              rows={3}
+              wrap="soft"
+              className="max-h-48 min-h-[84px] w-full resize-y rounded-[var(--radius-md)] border border-[var(--color-outline-variant)]/40 bg-[var(--color-surface)] px-3 py-2 text-sm leading-relaxed text-[var(--color-text-primary)] placeholder:text-[var(--color-text-tertiary)] focus:border-[var(--color-secondary)] focus:outline-none focus:ring-1 focus:ring-[var(--color-secondary)]/30"
             />
           </div>
         )}
diff --git a/desktop/src/components/chat/MessageList.test.tsx b/desktop/src/components/chat/MessageList.test.tsx
index 12b66416..f03f1c18 100644
--- a/desktop/src/components/chat/MessageList.test.tsx
+++ b/desktop/src/components/chat/MessageList.test.tsx
@@ -153,6 +153,104 @@ describe('MessageList nested tool calls', () => {
     expect(container.querySelector('[data-virtual-message-item]')).toBeNull()
   })
 
+  it('filters duplicate unresolved AskUserQuestion cards while a matching permission is pending', () => {
+    const messages: UIMessage[] = [
+      {
+        id: 'stale-ask',
+        type: 'tool_use',
+        toolName: 'AskUserQuestion',
+        toolUseId: 'stale-tool',
+        input: {
+          questions: [
+            {
+              question: 'Restore this context?',
+              options: [{ label: 'No' }, { label: 'Yes' }],
+            },
+          ],
+        },
+        timestamp: 1,
+      },
+      {
+        id: 'active-ask',
+        type: 'tool_use',
+        toolName: 'AskUserQuestion',
+        toolUseId: 'active-tool',
+        input: {
+          questions: [
+            {
+              question: 'Restore this context?',
+              options: [{ label: 'No' }, { label: 'Yes' }],
+            },
+          ],
+        },
+        timestamp: 2,
+      },
+    ]
+
+    const { renderItems } = buildRenderModel(messages, 'active-tool')
+
+    expect(renderItems).toHaveLength(1)
+    expect(renderItems[0]).toMatchObject({
+      kind: 'message',
+      message: {
+        type: 'tool_use',
+        toolName: 'AskUserQuestion',
+        toolUseId: 'active-tool',
+      },
+    })
+  })
+
+  it('keeps resolved AskUserQuestion history visible when filtering active duplicates', () => {
+    const messages: UIMessage[] = [
+      {
+        id: 'answered-ask',
+        type: 'tool_use',
+        toolName: 'AskUserQuestion',
+        toolUseId: 'answered-tool',
+        input: {
+          questions: [
+            {
+              question: 'Already answered?',
+              options: [{ label: 'No' }, { label: 'Yes' }],
+            },
+          ],
+        },
+        timestamp: 1,
+      },
+      {
+        id: 'answered-result',
+        type: 'tool_result',
+        toolUseId: 'answered-tool',
+        content: { answers: { 'Already answered?': 'Yes' } },
+        isError: false,
+        timestamp: 2,
+      },
+      {
+        id: 'active-ask',
+        type: 'tool_use',
+        toolName: 'AskUserQuestion',
+        toolUseId: 'active-tool',
+        input: {
+          questions: [
+            {
+              question: 'Restore this context?',
+              options: [{ label: 'No' }, { label: 'Yes' }],
+            },
+          ],
+        },
+        timestamp: 3,
+      },
+    ]
+
+    const { renderItems } = buildRenderModel(messages, 'active-tool')
+
+    expect(renderItems).toHaveLength(2)
+    expect(renderItems.map((item) => item.kind === 'message' && item.message.type === 'tool_use'
+      ? item.message.toolUseId
+      : null,
+    )).toEqual(['answered-tool', 'active-tool'])
+  })
+
   it('renders goal events as visible status cards', () => {
     useChatStore.setState({
       sessions: {
diff --git a/desktop/src/components/chat/MessageList.tsx b/desktop/src/components/chat/MessageList.tsx
index 4ccb58f6..3b9da434 100644
--- a/desktop/src/components/chat/MessageList.tsx
+++ b/desktop/src/components/chat/MessageList.tsx
@@ -447,11 +447,12 @@ function appendChildToolCall(
   }
 }
 
-export function buildRenderModel(messages: UIMessage[]): RenderModel {
+export function buildRenderModel(messages: UIMessage[], activeAskUserQuestionToolUseId?: string | null): RenderModel {
   const items: RenderItem[] = []
   const toolResultMap = new Map<string, ToolResult>()
   const childToolCallsByParent = new Map<string, ToolCall[]>()
   const toolUseIds = new Set<string>()
+  const lastUnresolvedAskUserQuestionIndexByToolUseId = new Map<string, number>()
   let pendingToolCalls: ToolCall[] = []
 
   const flushGroup = () => {
@@ -482,6 +483,15 @@ export function buildRenderModel(messages: UIMessage[]): RenderModel {
       toolResultMap.set(msg.toolUseId, msg)
     }
   }
+  messages.forEach((msg, index) => {
+    if (
+      msg.type === 'tool_use' &&
+      msg.toolName === 'AskUserQuestion' &&
+      !toolResultMap.has(msg.toolUseId)
+    ) {
+      lastUnresolvedAskUserQuestionIndexByToolUseId.set(msg.toolUseId, index)
+    }
+  })
 
   for (const msg of messages) {
     if (msg.type === 'assistant_text' && !msg.content.trim()) {
@@ -505,6 +515,18 @@ export function buildRenderModel(messages: UIMessage[]): RenderModel {
         continue
       }
       if (msg.toolName === 'AskUserQuestion') {
+        const isResolved = toolResultMap.has(msg.toolUseId)
+        const lastUnresolvedIndex = lastUnresolvedAskUserQuestionIndexByToolUseId.get(msg.toolUseId)
+        if (!isResolved && lastUnresolvedIndex !== undefined && messages[lastUnresolvedIndex] !== msg) {
+          continue
+        }
+        if (
+          !isResolved &&
+          activeAskUserQuestionToolUseId &&
+          msg.toolUseId !== activeAskUserQuestionToolUseId
+        ) {
+          continue
+        }
         flushGroup()
         items.push({ kind: 'message', message: msg })
       } else {
@@ -822,6 +844,10 @@ export function MessageList({ sessionId, compact = false }: MessageListProps = {
   const streamingText = sessionState?.streamingText ?? ''
   const activeThinkingId = sessionState?.activeThinkingId ?? null
   const agentTaskNotifications = sessionState?.agentTaskNotifications ?? {}
+  const activeAskUserQuestionToolUseId =
+    sessionState?.pendingPermission?.toolName === 'AskUserQuestion'
+      ? sessionState.pendingPermission.toolUseId
+      : null
   const shouldFollowContentResize =
     streamingText.trim().length > 0 ||
     chatState === 'streaming' ||
@@ -975,8 +1001,8 @@ export function MessageList({ sessionId, compact = false }: MessageListProps = {
   }, [scrollToBottom, shouldFollowContentResize])
 
   const { toolResultMap, childToolCallsByParent, renderItems } = useMemo(
-    () => buildRenderModel(messages),
-    [messages],
+    () => buildRenderModel(messages, activeAskUserQuestionToolUseId),
+    [activeAskUserQuestionToolUseId, messages],
   )
   const branchableMessageTargets = useMemo(
     () => branchActionsDisabled ? new Map<string, BranchableMessageTarget>() : getBranchableMessageTargets(messages),