diff --git a/src/renderer/src/components/native-chat/native-chat-runtime-send-launch-draft.test.ts b/src/renderer/src/components/native-chat/native-chat-runtime-send-launch-draft.test.ts
index 41b510e2b50..35837d3e029 100644
--- a/src/renderer/src/components/native-chat/native-chat-runtime-send-launch-draft.test.ts
+++ b/src/renderer/src/components/native-chat/native-chat-runtime-send-launch-draft.test.ts
@@ -13,6 +13,7 @@ vi.mock('@/runtime/runtime-terminal-inspection', () => ({
 import {
   NATIVE_CHAT_CLEAR_CONFIRM_MS,
   NATIVE_CHAT_CLEAR_UNSUBMITTED_INPUT,
+  NATIVE_CHAT_IMAGE_ATTACHMENT_SETTLE_MS,
   NATIVE_CHAT_SUBMIT_DELAY_MS,
   resetNativeChatPtySendQueuesForTests,
   sendNativeChatMessage,
@@ -103,6 +104,25 @@ describe('sendNativeChatMessage with a parked multi-line draft', () => {
       NATIVE_CHAT_SUBMIT_DELAY_MS + NATIVE_CHAT_CLEAR_CONFIRM_MS
     )
   })
+
+  it('submits before a queued send starts after clear confirmation', async () => {
+    const clearInput = buildAgentTuiClearInputForText(DRAFT)
+    sendNativeChatMessage(SETTINGS, PTY, 'first', {
+      clearInput,
+      confirmCleared: () => true
+    })
+    sendNativeChatMessage(SETTINGS, PTY, 'second')
+
+    await vi.advanceTimersByTimeAsync(NATIVE_CHAT_CLEAR_CONFIRM_MS + NATIVE_CHAT_SUBMIT_DELAY_MS)
+
+    expect(writes()).toEqual([
+      clearInput,
+      buildNativeChatPasteBytes('first'),
+      NATIVE_CHAT_SUBMIT,
+      NATIVE_CHAT_CLEAR_UNSUBMITTED_INPUT,
+      buildNativeChatPasteBytes('second')
+    ])
+  })
 })
 
 describe('image sends with a parked multi-line draft', () => {
@@ -122,4 +142,23 @@ describe('image sends with a parked multi-line draft', () => {
     vi.advanceTimersByTime(10_000)
     expect(writes().filter((write) => write === clearInput)).toHaveLength(1)
   })
+
+  it('submits the image send before a queued message starts', async () => {
+    const clearInput = buildAgentTuiClearInputForText(DRAFT)
+    sendNativeChatMessageWithImageAttachments(SETTINGS, PTY, 'caption', ['/tmp/a.png'], {
+      clearInput,
+      confirmCleared: () => true
+    })
+    sendNativeChatMessage(SETTINGS, PTY, 'second')
+
+    await vi.advanceTimersByTimeAsync(
+      NATIVE_CHAT_CLEAR_CONFIRM_MS +
+        NATIVE_CHAT_IMAGE_ATTACHMENT_SETTLE_MS +
+        NATIVE_CHAT_SUBMIT_DELAY_MS
+    )
+
+    expect(writes().indexOf(NATIVE_CHAT_SUBMIT)).toBeLessThan(
+      writes().indexOf(NATIVE_CHAT_CLEAR_UNSUBMITTED_INPUT)
+    )
+  })
 })
diff --git a/src/renderer/src/components/native-chat/native-chat-runtime-send.ts b/src/renderer/src/components/native-chat/native-chat-runtime-send.ts
index e1f5e5ca18d..3f2544c7323 100644
--- a/src/renderer/src/components/native-chat/native-chat-runtime-send.ts
+++ b/src/renderer/src/components/native-chat/native-chat-runtime-send.ts
@@ -130,15 +130,15 @@ export function sendNativeChatMessage(
       if (isCancelled()) {
         return
       }
+      delay(NATIVE_CHAT_SUBMIT_DELAY_MS + clearConfirmDurationMs(options), () => {
+        sendRuntimePtyInput(settings, ptyId, NATIVE_CHAT_SUBMIT)
+        markSubmitted()
+      })
       clearThenWrite(settings, ptyId, options, delay, () => {
         if (isCancelled()) {
           return
         }
         sendRuntimePtyInput(settings, ptyId, buildNativeChatPasteBytes(text))
-        delay(NATIVE_CHAT_SUBMIT_DELAY_MS, () => {
-          sendRuntimePtyInput(settings, ptyId, NATIVE_CHAT_SUBMIT)
-          markSubmitted()
-        })
       })
     },
     {
@@ -225,6 +225,16 @@ export function sendNativeChatMessageWithImageAttachments(
       if (isCancelled()) {
         return
       }
+      const clearConfirmMs = clearConfirmDurationMs(options)
+      if (trimmedText.length > 0) {
+        delay(clearConfirmMs + NATIVE_CHAT_IMAGE_ATTACHMENT_SETTLE_MS, () => {
+          sendRuntimePtyInput(settings, ptyId, buildNativeChatPasteBytes(text))
+        })
+      }
+      delay(durationMs, () => {
+        sendRuntimePtyInput(settings, ptyId, NATIVE_CHAT_SUBMIT)
+        markSubmitted()
+      })
       clearThenWrite(settings, ptyId, options, delay, () => {
         if (isCancelled()) {
           return
@@ -232,20 +242,6 @@ export function sendNativeChatMessageWithImageAttachments(
         for (const imagePath of imagePaths) {
           sendRuntimePtyInput(settings, ptyId, buildNativeChatImagePasteBytes(imagePath))
         }
-        if (trimmedText.length > 0) {
-          delay(NATIVE_CHAT_IMAGE_ATTACHMENT_SETTLE_MS, () => {
-            sendRuntimePtyInput(settings, ptyId, buildNativeChatPasteBytes(text))
-          })
-          delay(NATIVE_CHAT_IMAGE_ATTACHMENT_SETTLE_MS + NATIVE_CHAT_SUBMIT_DELAY_MS, () => {
-            sendRuntimePtyInput(settings, ptyId, NATIVE_CHAT_SUBMIT)
-            markSubmitted()
-          })
-          return
-        }
-        delay(NATIVE_CHAT_SUBMIT_DELAY_MS, () => {
-          sendRuntimePtyInput(settings, ptyId, NATIVE_CHAT_SUBMIT)
-          markSubmitted()
-        })
       })
     },
     {