diff --git a/examples/desktop/src/renderer/renderer.js b/examples/desktop/src/renderer/renderer.js
index 3af4cb841f..c092e4ac8e 100644
--- a/examples/desktop/src/renderer/renderer.js
+++ b/examples/desktop/src/renderer/renderer.js
@@ -6635,17 +6635,43 @@ async function dispatchPrompt(sid, text, opts = {}) {
   const meta = state.sessions.get(sid)
   if (meta) meta.running = true
   try {
-    await window.dsh.sendPrompt(sid, text)
+    await sendPromptSettleAware(sid, text, !!opts.settleRetry)
   } catch (err) {
     // Surface the error on the stream (matches the live-send path). We do
     // NOT clear the rest of the queue — a failed drain leaves the remaining
     // items parked so the user can retry / edit rather than losing them.
     appendSystem(`error: ${err.message}`)
+    // A drained message that ultimately failed goes BACK to the queue head
+    // (enqueue + promote) instead of vanishing — the strip stays the source
+    // of truth for "not yet delivered". The already-painted optimistic
+    // bubble stays; the echo adopts it on the eventual successful send.
+    if (opts.requeueOnFailure && msgQueue) {
+      const id = msgQueue.enqueue(sid, text)
+      if (id) msgQueue.promote(sid, id)
+      renderMsgQueueStrip()
+    }
   } finally {
     if (isActive) sendBtn.disabled = false
   }
 }
 
+// The daemon releases a session's prompt reservation at prompt SETTLEMENT,
+// which can lag the turn/end EVENT by a beat — a drain firing exactly on
+// turn/end can hit "session already has an active prompt" even though the
+// turn is over (observed live 2026-07-20 on stdio-deepseek). Retry only that
+// error, with a short backoff ladder; anything else throws immediately.
+async function sendPromptSettleAware(sid, text, settleRetry) {
+  const delays = settleRetry ? [250, 500, 1000, 2000] : []
+  for (;;) {
+    try {
+      return await window.dsh.sendPrompt(sid, text)
+    } catch (err) {
+      if (delays.length === 0 || !/already has an active prompt/i.test(String(err && err.message))) throw err
+      await new Promise((resolve) => setTimeout(resolve, delays.shift()))
+    }
+  }
+}
+
 // Drain exactly one queued message for `sessionId` and send it — guarded so
 // it fires at most once per turn even when both turn/end and
 // session.finished arrive for the same turn. The `_turnDrainPending` flag is
@@ -6666,7 +6692,14 @@ async function drainMsgQueueOnce(sessionId) {
   const next = msgQueue.drain(sessionId)
   renderMsgQueueStrip()
   if (!next) return
-  await dispatchPrompt(sessionId, next.text, { clearComposer: false })
+  await dispatchPrompt(sessionId, next.text, {
+    clearComposer: false,
+    // Drains race the daemon's prompt-reservation release (turn/end event
+    // precedes settlement); retry that one error briefly, and park the
+    // message back at the queue head if it still can't get through.
+    settleRetry: true,
+    requeueOnFailure: true,
+  })
 }
 
 async function cancel() {
diff --git a/examples/desktop/test/renderer-msg-queue.test.js b/examples/desktop/test/renderer-msg-queue.test.js
index 76fcc23983..f16f4486aa 100644
--- a/examples/desktop/test/renderer-msg-queue.test.js
+++ b/examples/desktop/test/renderer-msg-queue.test.js
@@ -194,3 +194,33 @@ test('drained send re-arms inflightTurn so a follow-up Enter queues again', asyn
   assert.equal(sendCalls(dsh).length, before, 'follow-up queued, not sent concurrently')
   assert.deepEqual(renderer.listMsgQueue('s1').map((x) => x.text), ['two', 'three'])
 })
+
+test('drain retries "already has an active prompt" then delivers (settle race)', async () => {
+  const { renderer, document, dsh } = await loadRenderer()
+  const { input } = await activeInflight(renderer, document)
+  input.value = 'parked message'; await renderer.send()
+  let calls = 0
+  dsh.sendPrompt = async (...args) => {
+    dsh.__calls.push(['sendPrompt', ...args])
+    calls += 1
+    if (calls === 1) throw new Error("Error invoking remote method 'session:prompt': Error: session already has an active prompt: x")
+    return { accepted: true }
+  }
+  renderer.onSessionEvent('s1', { type: 'turn/end', seq: 2 })
+  // Retry ladder's first rung is 250ms — wait past it.
+  await new Promise((resolve) => setTimeout(resolve, 450))
+  assert.equal(calls, 2, 'second attempt fired after the settle retry')
+  assert.equal(renderer.listMsgQueue('s1').length, 0, 'queue emptied — message delivered, not dropped')
+})
+
+test('drain requeues at head when the send keeps failing (no message loss)', async () => {
+  const { renderer, document, dsh } = await loadRenderer()
+  const { input } = await activeInflight(renderer, document)
+  input.value = 'doomed message'; await renderer.send()
+  dsh.sendPrompt = async () => { throw new Error('some hard transport failure') }
+  renderer.onSessionEvent('s1', { type: 'turn/end', seq: 2 })
+  await new Promise((resolve) => setTimeout(resolve, 30))
+  const parked = renderer.listMsgQueue('s1')
+  assert.equal(parked.length, 1, 'failed drain went back to the queue')
+  assert.equal(parked[0].text, 'doomed message')
+})