diff --git a/src/renderer/src/components/native-chat/session/terminal/send/use-native-chat-interactive-send.test.tsx b/src/renderer/src/components/native-chat/session/terminal/send/use-native-chat-interactive-send.test.tsx
new file mode 100644
index 00000000000..bce39608f40
--- /dev/null
+++ b/src/renderer/src/components/native-chat/session/terminal/send/use-native-chat-interactive-send.test.tsx
@@ -0,0 +1,125 @@
+// @vitest-environment happy-dom
+
+import { act, cleanup, renderHook } from '@testing-library/react'
+import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest'
+import type { AgentStatusEntry } from '../../../../../../../shared/agent-status/contracts/agent-status-types'
+import { AGENT_INTERRUPT_SETTLE_MS } from '../../../../../../../shared/agent-status/lifecycle/agent-interrupt-intent'
+
+const mocks = vi.hoisted(() => ({
+  inferInterrupt: vi.fn(() => Promise.resolve(true)),
+  inferQuestionAnswered: vi.fn(() => Promise.resolve(true)),
+  sendRuntimePtyInputVerified: vi.fn((..._args: unknown[]) => Promise.resolve(true))
+}))
+
+vi.mock('@/runtime/hosted-terminals/input/runtime-terminal-verified-input', () => ({
+  sendRuntimePtyInputVerified: (...args: unknown[]) => mocks.sendRuntimePtyInputVerified(...args)
+}))
+
+import { useAppStore } from '../../../../../store/index'
+import { useNativeChatInteractiveSend } from './use-native-chat-interactive-send'
+
+const PANE_KEY = 'tab-1:11111111-1111-4111-8111-111111111111'
+const initialState = useAppStore.getInitialState()
+
+function workingStatus(prompt: string, startedAt: number): AgentStatusEntry {
+  return {
+    state: 'working',
+    prompt,
+    updatedAt: startedAt,
+    stateStartedAt: startedAt,
+    agentType: 'openclaude',
+    paneKey: PANE_KEY,
+    stateHistory: []
+  }
+}
+
+describe('useNativeChatInteractiveSend Stop interrupt inference', () => {
+  beforeEach(() => {
+    vi.useFakeTimers()
+    vi.setSystemTime(10_000)
+    vi.clearAllMocks()
+    useAppStore.setState(initialState, true)
+    Object.defineProperty(window, 'api', {
+      configurable: true,
+      value: {
+        agentStatus: {
+          inferQuestionAnswered: mocks.inferQuestionAnswered,
+          inferInterrupt: mocks.inferInterrupt
+        }
+      }
+    })
+  })
+
+  afterEach(() => {
+    cleanup()
+    useAppStore.setState(initialState, true)
+    vi.useRealTimers()
+  })
+
+  it.each([
+    [true, 1],
+    [false, 0]
+  ] as const)(
+    'gives an openclaude Stop (Escape accepted: %s) the interrupt inference a typed Escape gets',
+    async (accepted, inferences) => {
+      const startedAt = 10_000
+      useAppStore.setState({
+        agentStatusByPaneKey: { [PANE_KEY]: workingStatus('run sleep 60', startedAt) }
+      })
+      mocks.sendRuntimePtyInputVerified.mockResolvedValueOnce(accepted)
+      const { result } = renderHook(() =>
+        useNativeChatInteractiveSend(PANE_KEY, 'pty-1', 'openclaude')
+      )
+
+      await act(async () => result.current.cancel())
+      expect(mocks.sendRuntimePtyInputVerified).toHaveBeenCalledWith('pty-1', '\x1b', 'driving', {
+        requireWriteSettlement: true
+      })
+      expect(mocks.inferInterrupt).not.toHaveBeenCalled()
+
+      await act(async () => {
+        vi.advanceTimersByTime(AGENT_INTERRUPT_SETTLE_MS)
+      })
+
+      expect(mocks.inferInterrupt).toHaveBeenCalledTimes(inferences)
+      if (inferences > 0) {
+        expect(mocks.inferInterrupt).toHaveBeenCalledWith({
+          paneKey: PANE_KEY,
+          baselineUpdatedAt: startedAt,
+          baselineStateStartedAt: startedAt,
+          baselinePrompt: 'run sleep 60',
+          baselineAgentType: 'openclaude',
+          intent: 'plain-escape'
+        })
+      }
+    }
+  )
+
+  // A slow remote acceptance must not settle a turn that started after the Stop.
+  it('infers a Stop from the status before its Escape, not a turn that began mid-send', async () => {
+    const startedAt = 10_000
+    useAppStore.setState({
+      agentStatusByPaneKey: { [PANE_KEY]: workingStatus('run sleep 60', startedAt) }
+    })
+    let accept: (accepted: boolean) => void = () => {}
+    mocks.sendRuntimePtyInputVerified.mockReturnValueOnce(
+      new Promise<boolean>((resolve) => {
+        accept = resolve
+      })
+    )
+    const { result } = renderHook(() =>
+      useNativeChatInteractiveSend(PANE_KEY, 'pty-1', 'openclaude')
+    )
+
+    act(() => result.current.cancel())
+    useAppStore.setState({
+      agentStatusByPaneKey: { [PANE_KEY]: workingStatus('next prompt', startedAt + 1) }
+    })
+    await act(async () => accept(true))
+    await act(async () => {
+      vi.advanceTimersByTime(AGENT_INTERRUPT_SETTLE_MS)
+    })
+
+    expect(mocks.inferInterrupt).not.toHaveBeenCalled()
+  })
+})
diff --git a/src/renderer/src/components/native-chat/session/terminal/send/use-native-chat-interactive-send.ts b/src/renderer/src/components/native-chat/session/terminal/send/use-native-chat-interactive-send.ts
index 6e2a6392654..676346cb98d 100644
--- a/src/renderer/src/components/native-chat/session/terminal/send/use-native-chat-interactive-send.ts
+++ b/src/renderer/src/components/native-chat/session/terminal/send/use-native-chat-interactive-send.ts
@@ -23,6 +23,7 @@ import {
   type NativeChatSendHandle
 } from './native-chat-runtime-send'
 import { inferQuestionAnsweredFromCurrentStatus } from '../../../../terminal-pane/agent-status/input-inference/agent-question-answered-inference'
+import { createAgentInterruptInference } from '../../../../terminal-pane/agent-status/input-inference/agent-interrupt-inference'
 
 // Agent TUIs use Escape to cancel questions or deny approvals.
 const ESC = '\x1b'
@@ -157,8 +158,23 @@ export function useNativeChatInteractiveSend(
       inFlightRef.current = sendNativeChatAskAnswer(targetPtyId, [{ raw: ESC }, { raw: ESC }])
       return
     }
-    sendRaw(ESC)
-  }, [agent, cancelInFlight, sendRaw, targetPtyId])
+    // Why: this Escape bypasses xterm.onData; infer like an acknowledged typed Escape, from the status before it.
+    const statusBeforeEscape = useAppStore.getState().agentStatusByPaneKey[paneKey] ?? null
+    void sendRawVerified(ESC).then((accepted) => {
+      if (!accepted) {
+        return
+      }
+      void createAgentInterruptInference({
+        paneKey,
+        getStatusEntry: () => useAppStore.getState().agentStatusByPaneKey[paneKey],
+        inferInterrupt: (request) =>
+          window.api.agentStatus.inferInterrupt(request).catch((err) => {
+            console.warn('[agent-interrupt] native-chat inference failed:', err)
+            return false
+          })
+      }).observeInputIntent('plain-escape', statusBeforeEscape)
+    })
+  }, [agent, cancelInFlight, paneKey, sendRawVerified, targetPtyId])
 
   return { sendAnswer, sendRaw, sendRawVerified, cancelPending: cancelInFlight, cancelAsk, cancel }
 }