diff --git a/.changeset/restore-vscode-prompt-history.md b/.changeset/restore-vscode-prompt-history.md
new file mode 100644
index 00000000000..e62af916e4d
--- /dev/null
+++ b/.changeset/restore-vscode-prompt-history.md
@@ -0,0 +1,5 @@
+---
+"kilo-code": patch
+---
+
+Restore the newest prompt to keyboard history when starting a new chat.
diff --git a/packages/kilo-vscode/tests/unit/prompt-input-connection-guard.test.ts b/packages/kilo-vscode/tests/unit/prompt-input-connection-guard.test.ts
index 96e8a2f1985..4c85ed00ce2 100644
--- a/packages/kilo-vscode/tests/unit/prompt-input-connection-guard.test.ts
+++ b/packages/kilo-vscode/tests/unit/prompt-input-connection-guard.test.ts
@@ -21,6 +21,23 @@ describe("PromptInput connection guard", () => {
     expect(send).toBeGreaterThan(guard)
     expect(clear).toBeGreaterThan(send)
   })
+
+  it("records a dispatched prompt before returning for a changed draft scope", () => {
+    // Regression source: fbe5f4cb in PR #11442 made fresh sends set draftSessionID synchronously,
+    // changing draftKey from :new to :pending:<uuid>. The changed key must block UI cleanup,
+    // but it must not skip recording the already-dispatched prompt in keyboard history.
+    const start = src.indexOf("const key = draftKey()")
+    const command = src.indexOf("session.sendCommand(", start)
+    const message = src.indexOf("session.sendMessage(", command)
+    const append = src.indexOf("history.append(draft)", message)
+    const guard = src.indexOf("if (draftKey() !== key) return", message)
+
+    expect(start).toBeGreaterThan(-1)
+    expect(command).toBeGreaterThan(start)
+    expect(message).toBeGreaterThan(command)
+    expect(append).toBeGreaterThan(message)
+    expect(guard).toBeGreaterThan(append)
+  })
 })
 
 describe("PromptInput sandbox toggle", () => {
diff --git a/packages/kilo-vscode/webview-ui/src/components/chat/PromptInput.tsx b/packages/kilo-vscode/webview-ui/src/components/chat/PromptInput.tsx
index b235cc8f8b6..7d29423113c 100644
--- a/packages/kilo-vscode/webview-ui/src/components/chat/PromptInput.tsx
+++ b/packages/kilo-vscode/webview-ui/src/components/chat/PromptInput.tsx
@@ -1079,9 +1079,9 @@ export const PromptInput: Component<PromptInputProps> = (props) => {
     reviewDrafts.delete(key)
     imageDrafts.delete(key)
     scrolls.delete(key)
+    history.append(draft)
     if (draftKey() !== key) return
 
-    history.append(draft)
     history.reset()
     setText("")
     clearReviewComments()