diff --git a/src/renderer/src/components/native-chat/native-chat-draft-cache.test.ts b/src/renderer/src/components/native-chat/native-chat-draft-cache.test.ts
index afd0129611e..2478c106143 100644
--- a/src/renderer/src/components/native-chat/native-chat-draft-cache.test.ts
+++ b/src/renderer/src/components/native-chat/native-chat-draft-cache.test.ts
@@ -66,12 +66,29 @@ describe('returnNativeChatDraftText', () => {
     expect(readNativeChatDraftCache('agent-session:s1')).toBe('typed meanwhile\n\nunsent message')
   })
 
-  it('is idempotent: text the draft already holds is not added again', () => {
+  it('is idempotent: text the draft already ends with is not added again', () => {
     returnNativeChatDraftText('agent-session:s1', 'unsent message')
     returnNativeChatDraftText('agent-session:s1', 'unsent message')
-    writeNativeChatDraftCache('agent-session:s1', 'before\n\nunsent message\n\nafter')
-    returnNativeChatDraftText('agent-session:s1', '\nunsent message  ')
-    expect(readNativeChatDraftCache('agent-session:s1')).toBe('before\n\nunsent message\n\nafter')
+    expect(readNativeChatDraftCache('agent-session:s1')).toBe('unsent message')
+    writeNativeChatDraftCache('agent-session:s1', 'before\n\nunsent message  \n')
+    returnNativeChatDraftText('agent-session:s1', 'unsent message  ')
+    expect(readNativeChatDraftCache('agent-session:s1')).toBe('before\n\nunsent message  \n')
+  })
+
+  it('still returns text that only appears inside a longer draft', () => {
+    writeNativeChatDraftCache('agent-session:s1', 'use the other algorithm and go')
+    returnNativeChatDraftText('agent-session:s1', 'go')
+    expect(readNativeChatDraftCache('agent-session:s1')).toBe(
+      'use the other algorithm and go\n\ngo'
+    )
+    writeNativeChatDraftCache('agent-session:s1', 'yes\n\nthen run the tests')
+    returnNativeChatDraftText('agent-session:s1', 'yes')
+    expect(readNativeChatDraftCache('agent-session:s1')).toBe('yes\n\nthen run the tests\n\nyes')
+  })
+
+  it("keeps the returned text's leading indentation", () => {
+    returnNativeChatDraftText('agent-session:s1', '    indented code\n')
+    expect(readNativeChatDraftCache('agent-session:s1')).toBe('    indented code')
   })
 
   it('puts no blank lines before text returned to a whitespace-only draft', () => {
diff --git a/src/renderer/src/components/native-chat/native-chat-draft-cache.ts b/src/renderer/src/components/native-chat/native-chat-draft-cache.ts
index b730beea333..89092a6d01b 100644
--- a/src/renderer/src/components/native-chat/native-chat-draft-cache.ts
+++ b/src/renderer/src/components/native-chat/native-chat-draft-cache.ts
@@ -60,16 +60,19 @@ export function appendNativeChatDraftCache(scopeKey: string, text: string): void
 
 /**
  * Hands text Orca could not deliver back to the person, with or without a composer showing it.
- * Why skipped when already there: a hand-back can repeat (a crash before its copy was removed,
- * two windows settling one message), and the person must see it once.
+ * Why skipped when the draft already ends with it: a hand-back can repeat (a crash before its copy
+ * was removed, two windows settling one message), and the person must see it once. Only the end
+ * counts, so text that merely appears inside a longer draft, or a second copy, still comes back.
  */
 export function returnNativeChatDraftText(scopeKey: string, text: string): void {
-  const returned = text.trim()
-  if (returned === '') {
+  // Only the end is trimmed, as a send trims it: a first line's indentation is part of the text.
+  const returned = text.trimEnd()
+  if (returned.trim() === '') {
     return
   }
   const previous = readNativeChatDraftCache(scopeKey)
-  if (previous.includes(returned)) {
+  const draft = previous.trimEnd()
+  if (draft === returned || draft.endsWith(`\n\n${returned}`)) {
     return
   }
   appendToDraft(scopeKey, returned, previous)