diff --git a/apps/desktop/src/app/chat/composer/index.tsx b/apps/desktop/src/app/chat/composer/index.tsx
index d41d25d1a23..37360f39f05 100644
--- a/apps/desktop/src/app/chat/composer/index.tsx
+++ b/apps/desktop/src/app/chat/composer/index.tsx
@@ -31,6 +31,7 @@ import {
   enqueueQueuedPrompt,
   type QueuedPromptEntry,
   removeQueuedPrompt,
+  shouldAutoDrainOnSettle,
   updateQueuedPrompt
 } from '@/store/composer-queue'
 import { $messages } from '@/store/session'
@@ -124,6 +125,12 @@ export function ChatBar({
   const draftRef = useRef(draft)
   const previousBusyRef = useRef(busy)
   const drainingQueueRef = useRef(false)
+  // Set when the user explicitly interrupts the running turn via the Stop
+  // button (busy + empty composer). It suppresses the next busy→false
+  // auto-drain so an explicit Stop actually halts instead of immediately
+  // firing the head of the queue. The queue is preserved; the user resumes
+  // it deliberately via Cmd/Ctrl+K, Enter, or the per-row "send now" arrow.
+  const userInterruptedRef = useRef(false)
   const urlInputRef = useRef<HTMLInputElement | null>(null)
 
   const [urlOpen, setUrlOpen] = useState(false)
@@ -859,26 +866,42 @@ export function ChatBar({
     [queueEdit, runDrain]
   )
 
-  const interruptAndSendNextQueued = useCallback(async () => {
-    if (queuedPrompts.length === 0) {
-      return false
-    }
-
-    await Promise.resolve(onCancel())
-
-    return drainNextQueued()
-  }, [drainNextQueued, onCancel, queuedPrompts.length])
-
-  // Auto-drain on busy → false (turn settled).
+  // Auto-drain on busy → false (turn settled). An explicit user interrupt
+  // (Stop button) sets userInterruptedRef so we skip exactly one auto-drain:
+  // the user asked to halt, so we must not immediately re-send the queue.
+  // The queued turns stay intact and the user resumes them on demand.
   useEffect(() => {
     const wasBusy = previousBusyRef.current
     previousBusyRef.current = busy
 
-    if (busy || !wasBusy || queuedPrompts.length === 0) {
+    // Clear the interrupt latch when a new turn starts (false → true). This
+    // guards the sub-frame race where a Stop click lands after busy already
+    // flipped false (button not yet unmounted): the stale latch can no longer
+    // survive into the next turn and wrongly suppress its natural auto-drain.
+    if (busy && !wasBusy) {
+      userInterruptedRef.current = false
+
       return
     }
 
-    void drainNextQueued()
+    const interrupted = userInterruptedRef.current
+
+    // Consume the interrupt latch on any settle so a later natural completion
+    // is not wrongly suppressed.
+    if (!busy && wasBusy && interrupted) {
+      userInterruptedRef.current = false
+    }
+
+    if (
+      shouldAutoDrainOnSettle({
+        isBusy: busy,
+        queueLength: queuedPrompts.length,
+        userInterrupted: interrupted,
+        wasBusy
+      })
+    ) {
+      void drainNextQueued()
+    }
   }, [busy, drainNextQueued, queuedPrompts.length])
 
   // Clean up queue edit when its target disappears (session swap or external delete).
@@ -901,9 +924,13 @@ export function ChatBar({
     } else if (busy) {
       if (hasComposerPayload) {
         queueCurrentDraft()
-      } else if (queuedPrompts.length > 0) {
-        void interruptAndSendNextQueued()
       } else {
+        // Stop button: an explicit interrupt must actually halt the running
+        // turn. Mark the interrupt so the busy→false auto-drain effect skips
+        // re-sending the queue — otherwise a queued follow-up would fire the
+        // instant we cancel and Stop would appear to "never work". Queued
+        // turns are preserved; the user sends them on demand.
+        userInterruptedRef.current = true
         triggerHaptic('cancel')
         void Promise.resolve(onCancel())
       }
diff --git a/apps/desktop/src/store/composer-queue.test.ts b/apps/desktop/src/store/composer-queue.test.ts
index 9f15232aecb..c00cc4c2b21 100644
--- a/apps/desktop/src/store/composer-queue.test.ts
+++ b/apps/desktop/src/store/composer-queue.test.ts
@@ -8,6 +8,7 @@ import {
   enqueueQueuedPrompt,
   getQueuedPrompts,
   removeQueuedPrompt,
+  shouldAutoDrainOnSettle,
   updateQueuedPrompt,
   updateQueuedPromptText
 } from './composer-queue'
@@ -100,3 +101,37 @@ describe('composer queue store', () => {
     expect(parsed[SESSION_KEY]?.[0]?.text).toBe('persist me')
   })
 })
+
+describe('shouldAutoDrainOnSettle', () => {
+  const base = { isBusy: false, queueLength: 1, userInterrupted: false, wasBusy: true }
+
+  it('drains the next queued prompt when a turn completes naturally', () => {
+    expect(shouldAutoDrainOnSettle(base)).toBe(true)
+  })
+
+  it('does NOT drain when the user explicitly interrupted (Stop button)', () => {
+    // Regression: previously the Stop button "never worked" because cancelling
+    // a turn flipped busy → false and the queue immediately re-fired its head.
+    expect(shouldAutoDrainOnSettle({ ...base, userInterrupted: true })).toBe(false)
+  })
+
+  it('does not drain when the queue is empty', () => {
+    expect(shouldAutoDrainOnSettle({ ...base, queueLength: 0 })).toBe(false)
+  })
+
+  it('does not drain when interrupted even if the queue is also empty', () => {
+    expect(shouldAutoDrainOnSettle({ ...base, queueLength: 0, userInterrupted: true })).toBe(false)
+  })
+
+  it('ignores steady busy state (no true → false transition)', () => {
+    expect(shouldAutoDrainOnSettle({ ...base, isBusy: true })).toBe(false)
+  })
+
+  it('ignores busy entry (false → true, not a settle)', () => {
+    expect(shouldAutoDrainOnSettle({ ...base, isBusy: true, wasBusy: false })).toBe(false)
+  })
+
+  it('ignores steady idle state (was not busy)', () => {
+    expect(shouldAutoDrainOnSettle({ ...base, wasBusy: false })).toBe(false)
+  })
+})
diff --git a/apps/desktop/src/store/composer-queue.ts b/apps/desktop/src/store/composer-queue.ts
index 3f231fb7b2a..9bc3f9270d6 100644
--- a/apps/desktop/src/store/composer-queue.ts
+++ b/apps/desktop/src/store/composer-queue.ts
@@ -188,3 +188,39 @@ export const clearQueuedPrompts = (key: string | null | undefined) => {
 
   writeSession(sid, [])
 }
+
+/** Inputs to {@link shouldAutoDrainOnSettle}, captured at a `busy` transition. */
+export interface AutoDrainSettleInput {
+  wasBusy: boolean
+  isBusy: boolean
+  queueLength: number
+  userInterrupted: boolean
+}
+
+/**
+ * Decide whether the composer should auto-drain the next queued prompt when a
+ * turn settles (busy transitions true → false).
+ *
+ * The queue auto-advances when a turn *completes naturally*, but must NOT
+ * advance when the user *explicitly interrupted* the turn via the Stop button.
+ * Conflating the two made the Stop button appear to "never work": cancelling a
+ * turn flipped busy → false, the queue immediately re-fired its head, and the
+ * agent kept running. An explicit interrupt means stop — the queued turns are
+ * preserved and the user resumes them deliberately (Cmd/Ctrl+K, Enter, or the
+ * per-row "send now" arrow).
+ */
+export const shouldAutoDrainOnSettle = (params: AutoDrainSettleInput): boolean => {
+  const { isBusy, queueLength, userInterrupted, wasBusy } = params
+
+  // Only react to a true → false transition; ignore steady state and entry.
+  if (isBusy || !wasBusy) {
+    return false
+  }
+
+  // An explicit Stop suppresses exactly one auto-drain.
+  if (userInterrupted) {
+    return false
+  }
+
+  return queueLength > 0
+}