diff --git a/packages/kilo-vscode/webview-ui/src/components/chat/ChatView.tsx b/packages/kilo-vscode/webview-ui/src/components/chat/ChatView.tsx
index 448f9e39d3a..6e6c106e162 100644
--- a/packages/kilo-vscode/webview-ui/src/components/chat/ChatView.tsx
+++ b/packages/kilo-vscode/webview-ui/src/components/chat/ChatView.tsx
@@ -134,7 +134,7 @@ export const ChatView: Component<ChatViewProps> = (props) => {
             </div>
           </Show>
           <Show when={!props.readonly}>
-            <PromptInput />
+            <PromptInput blocked={blocked} />
           </Show>
         </div>
       </Show>
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 0a8332605d5..a9759a6c575 100644
--- a/packages/kilo-vscode/webview-ui/src/components/chat/PromptInput.tsx
+++ b/packages/kilo-vscode/webview-ui/src/components/chat/PromptInput.tsx
@@ -41,7 +41,11 @@ function mergeReviewComments(current: ReviewComment[], incoming: ReviewComment[]
   return [...map.values()]
 }
 
-export const PromptInput: Component = () => {
+interface PromptInputProps {
+  blocked?: () => boolean
+}
+
+export const PromptInput: Component<PromptInputProps> = (props) => {
   const session = useSession()
   const server = useServer()
   const language = useLanguage()
@@ -172,7 +176,7 @@ export const PromptInput: Component = () => {
   const isBusy = () => session.status() === "busy"
   const isDisabled = () => !server.isConnected()
   const hasInput = () => text().trim().length > 0 || imageAttach.images().length > 0 || reviewComments().length > 0
-  const canSend = () => hasInput() && !isDisabled()
+  const canSend = () => hasInput() && !isDisabled() && !props.blocked?.()
   const showStop = () => isBusy() && !hasInput()
   const placeholder = () => {
     switch (server.connectionState()) {
@@ -450,7 +454,7 @@ export const PromptInput: Component = () => {
     const pending = reviewComments()
     const review = pending.length > 0 ? formatReviewCommentsMarkdown(pending) : ""
     const message = draft && review ? `${review}\n\n${draft}` : draft || review
-    if ((!message && imgs.length === 0) || isDisabled()) return
+    if ((!message && imgs.length === 0) || isDisabled() || props.blocked?.()) return
 
     const mentionFiles = mention.parseFileAttachments(draft)
     const imgFiles = imgs.map((img) => ({ mime: img.mime, url: img.dataUrl, filename: img.filename }))
@@ -639,7 +643,10 @@ export const PromptInput: Component = () => {
           <Show
             when={showStop()}
             fallback={
-              <Tooltip value={language.t("prompt.action.send")} placement="top">
+              <Tooltip
+                value={props.blocked?.() ? language.t("prompt.action.send.blocked") : language.t("prompt.action.send")}
+                placement="top"
+              >
                 <Button
                   variant="ghost"
                   size="small"
diff --git a/packages/kilo-vscode/webview-ui/src/i18n/ar.ts b/packages/kilo-vscode/webview-ui/src/i18n/ar.ts
index c4fa3f25acb..5c369fdb3ac 100644
--- a/packages/kilo-vscode/webview-ui/src/i18n/ar.ts
+++ b/packages/kilo-vscode/webview-ui/src/i18n/ar.ts
@@ -229,6 +229,7 @@ export const dict = {
   "prompt.action.attachFile": "إرفاق ملف",
   "prompt.attachment.remove": "إزالة المرفق",
   "prompt.action.send": "إرسال",
+  "prompt.action.send.blocked": "أجب عن السؤال المعلق أو تجاهله أولاً",
   "prompt.action.stop": "توقف",
   "prompt.action.enhance": "تحسين النص",
   "prompt.action.resetModel": "إعادة تعيين النموذج إلى الافتراضي",
diff --git a/packages/kilo-vscode/webview-ui/src/i18n/br.ts b/packages/kilo-vscode/webview-ui/src/i18n/br.ts
index e8a16504af0..f6a6989a2e8 100644
--- a/packages/kilo-vscode/webview-ui/src/i18n/br.ts
+++ b/packages/kilo-vscode/webview-ui/src/i18n/br.ts
@@ -230,6 +230,7 @@ export const dict = {
   "prompt.action.attachFile": "Anexar arquivo",
   "prompt.attachment.remove": "Remover anexo",
   "prompt.action.send": "Enviar",
+  "prompt.action.send.blocked": "Responda ou feche a pergunta pendente primeiro",
   "prompt.action.stop": "Parar",
   "prompt.action.enhance": "Melhorar prompt",
   "prompt.action.resetModel": "Redefinir modelo para o padrão",
diff --git a/packages/kilo-vscode/webview-ui/src/i18n/bs.ts b/packages/kilo-vscode/webview-ui/src/i18n/bs.ts
index 5097fd6a307..d48fe6e7892 100644
--- a/packages/kilo-vscode/webview-ui/src/i18n/bs.ts
+++ b/packages/kilo-vscode/webview-ui/src/i18n/bs.ts
@@ -231,6 +231,7 @@ export const dict = {
   "prompt.action.attachFile": "Priloži datoteku",
   "prompt.attachment.remove": "Ukloni prilog",
   "prompt.action.send": "Pošalji",
+  "prompt.action.send.blocked": "Prvo odgovorite ili odbacite pitanje na čekanju",
   "prompt.action.stop": "Zaustavi",
   "prompt.action.enhance": "Poboljšaj prompt",
   "prompt.action.resetModel": "Resetuj model na zadani",
diff --git a/packages/kilo-vscode/webview-ui/src/i18n/da.ts b/packages/kilo-vscode/webview-ui/src/i18n/da.ts
index 1e979d37779..92a32f99213 100644
--- a/packages/kilo-vscode/webview-ui/src/i18n/da.ts
+++ b/packages/kilo-vscode/webview-ui/src/i18n/da.ts
@@ -230,6 +230,7 @@ export const dict = {
   "prompt.action.attachFile": "Vedhæft fil",
   "prompt.attachment.remove": "Fjern vedhæftning",
   "prompt.action.send": "Send",
+  "prompt.action.send.blocked": "Besvar eller afvis det afventende spørgsmål først",
   "prompt.action.stop": "Stop",
   "prompt.action.enhance": "Forbedr prompt",
   "prompt.action.resetModel": "Nulstil model til standard",
diff --git a/packages/kilo-vscode/webview-ui/src/i18n/de.ts b/packages/kilo-vscode/webview-ui/src/i18n/de.ts
index 99f0f585e0a..3e8faf74290 100644
--- a/packages/kilo-vscode/webview-ui/src/i18n/de.ts
+++ b/packages/kilo-vscode/webview-ui/src/i18n/de.ts
@@ -234,6 +234,7 @@ export const dict = {
   "prompt.action.attachFile": "Datei anhängen",
   "prompt.attachment.remove": "Anhang entfernen",
   "prompt.action.send": "Senden",
+  "prompt.action.send.blocked": "Beantworten oder verwerfen Sie zuerst die ausstehende Frage",
   "prompt.action.stop": "Stopp",
   "prompt.action.enhance": "Prompt verbessern",
   "prompt.action.resetModel": "Modell auf Standard zurücksetzen",
diff --git a/packages/kilo-vscode/webview-ui/src/i18n/en.ts b/packages/kilo-vscode/webview-ui/src/i18n/en.ts
index 23eef2801c6..a790127685d 100644
--- a/packages/kilo-vscode/webview-ui/src/i18n/en.ts
+++ b/packages/kilo-vscode/webview-ui/src/i18n/en.ts
@@ -231,6 +231,7 @@ export const dict = {
   "prompt.action.attachFile": "Attach file",
   "prompt.attachment.remove": "Remove attachment",
   "prompt.action.send": "Send",
+  "prompt.action.send.blocked": "Answer or dismiss the pending question first",
   "prompt.action.stop": "Stop",
   "prompt.action.enhance": "Enhance prompt",
   "prompt.action.resetModel": "Reset model to default",
diff --git a/packages/kilo-vscode/webview-ui/src/i18n/es.ts b/packages/kilo-vscode/webview-ui/src/i18n/es.ts
index 47d663824f3..2f05b99b27e 100644
--- a/packages/kilo-vscode/webview-ui/src/i18n/es.ts
+++ b/packages/kilo-vscode/webview-ui/src/i18n/es.ts
@@ -230,6 +230,7 @@ export const dict = {
   "prompt.action.attachFile": "Adjuntar archivo",
   "prompt.attachment.remove": "Eliminar adjunto",
   "prompt.action.send": "Enviar",
+  "prompt.action.send.blocked": "Responda o descarte la pregunta pendiente primero",
   "prompt.action.stop": "Detener",
   "prompt.action.enhance": "Mejorar prompt",
   "prompt.action.resetModel": "Restablecer modelo al predeterminado",
diff --git a/packages/kilo-vscode/webview-ui/src/i18n/fr.ts b/packages/kilo-vscode/webview-ui/src/i18n/fr.ts
index da0135db55d..a9a877d78dd 100644
--- a/packages/kilo-vscode/webview-ui/src/i18n/fr.ts
+++ b/packages/kilo-vscode/webview-ui/src/i18n/fr.ts
@@ -231,6 +231,7 @@ export const dict = {
   "prompt.action.attachFile": "Joindre un fichier",
   "prompt.attachment.remove": "Supprimer la pièce jointe",
   "prompt.action.send": "Envoyer",
+  "prompt.action.send.blocked": "Répondez ou rejetez d'abord la question en attente",
   "prompt.action.stop": "Arrêter",
   "prompt.action.enhance": "Améliorer le prompt",
   "prompt.action.resetModel": "Réinitialiser le modèle par défaut",
diff --git a/packages/kilo-vscode/webview-ui/src/i18n/ja.ts b/packages/kilo-vscode/webview-ui/src/i18n/ja.ts
index 7c7e68c0ced..a6e05c59afb 100644
--- a/packages/kilo-vscode/webview-ui/src/i18n/ja.ts
+++ b/packages/kilo-vscode/webview-ui/src/i18n/ja.ts
@@ -229,6 +229,7 @@ export const dict = {
   "prompt.action.attachFile": "ファイルを添付",
   "prompt.attachment.remove": "添付ファイルを削除",
   "prompt.action.send": "送信",
+  "prompt.action.send.blocked": "最初に保留中の質問に答えるか、閉じてください",
   "prompt.action.stop": "停止",
   "prompt.action.enhance": "プロンプトを改善",
   "prompt.action.resetModel": "モデルをデフォルトにリセット",
diff --git a/packages/kilo-vscode/webview-ui/src/i18n/ko.ts b/packages/kilo-vscode/webview-ui/src/i18n/ko.ts
index db088d27173..81ff34c49f3 100644
--- a/packages/kilo-vscode/webview-ui/src/i18n/ko.ts
+++ b/packages/kilo-vscode/webview-ui/src/i18n/ko.ts
@@ -233,6 +233,7 @@ export const dict = {
   "prompt.action.attachFile": "파일 첨부",
   "prompt.attachment.remove": "첨부 파일 제거",
   "prompt.action.send": "전송",
+  "prompt.action.send.blocked": "먼저 대기 중인 질문에 답하거나 닫아주세요",
   "prompt.action.stop": "중지",
   "prompt.action.enhance": "프롬프트 개선",
   "prompt.action.resetModel": "모델을 기본값으로 재설정",
diff --git a/packages/kilo-vscode/webview-ui/src/i18n/no.ts b/packages/kilo-vscode/webview-ui/src/i18n/no.ts
index 5a5205d4532..1afdf0d376e 100644
--- a/packages/kilo-vscode/webview-ui/src/i18n/no.ts
+++ b/packages/kilo-vscode/webview-ui/src/i18n/no.ts
@@ -233,6 +233,7 @@ export const dict = {
   "prompt.action.attachFile": "Legg ved fil",
   "prompt.attachment.remove": "Fjern vedlegg",
   "prompt.action.send": "Send",
+  "prompt.action.send.blocked": "Svar på eller avvis det ventende spørsmålet først",
   "prompt.action.stop": "Stopp",
   "prompt.action.enhance": "Forbedre prompt",
   "prompt.action.resetModel": "Tilbakestill modell til standard",
diff --git a/packages/kilo-vscode/webview-ui/src/i18n/pl.ts b/packages/kilo-vscode/webview-ui/src/i18n/pl.ts
index 97923dc9774..c6271d13ebc 100644
--- a/packages/kilo-vscode/webview-ui/src/i18n/pl.ts
+++ b/packages/kilo-vscode/webview-ui/src/i18n/pl.ts
@@ -230,6 +230,7 @@ export const dict = {
   "prompt.action.attachFile": "Załącz plik",
   "prompt.attachment.remove": "Usuń załącznik",
   "prompt.action.send": "Wyślij",
+  "prompt.action.send.blocked": "Najpierw odpowiedz na oczekujące pytanie lub je odrzuć",
   "prompt.action.stop": "Zatrzymaj",
   "prompt.action.enhance": "Ulepsz prompt",
   "prompt.action.resetModel": "Zresetuj model do domyślnego",
diff --git a/packages/kilo-vscode/webview-ui/src/i18n/ru.ts b/packages/kilo-vscode/webview-ui/src/i18n/ru.ts
index 08100091c9e..c053b8eecf6 100644
--- a/packages/kilo-vscode/webview-ui/src/i18n/ru.ts
+++ b/packages/kilo-vscode/webview-ui/src/i18n/ru.ts
@@ -230,6 +230,7 @@ export const dict = {
   "prompt.action.attachFile": "Прикрепить файл",
   "prompt.attachment.remove": "Удалить вложение",
   "prompt.action.send": "Отправить",
+  "prompt.action.send.blocked": "Сначала ответьте на ожидающий вопрос или отклоните его",
   "prompt.action.stop": "Остановить",
   "prompt.action.enhance": "Улучшить промпт",
   "prompt.action.resetModel": "Сбросить модель на значение по умолчанию",
diff --git a/packages/kilo-vscode/webview-ui/src/i18n/th.ts b/packages/kilo-vscode/webview-ui/src/i18n/th.ts
index cdfd4b6bf06..4f8b251c94f 100644
--- a/packages/kilo-vscode/webview-ui/src/i18n/th.ts
+++ b/packages/kilo-vscode/webview-ui/src/i18n/th.ts
@@ -230,6 +230,7 @@ export const dict = {
   "prompt.action.attachFile": "แนบไฟล์",
   "prompt.attachment.remove": "เอาไฟล์แนบออก",
   "prompt.action.send": "ส่ง",
+  "prompt.action.send.blocked": "โปรดตอบหรือข้ามคำถามที่รอดำเนินการก่อน",
   "prompt.action.stop": "หยุด",
   "prompt.action.enhance": "ปรับปรุงพรอมต์",
   "prompt.action.resetModel": "รีเซ็ตโมเดลเป็นค่าเริ่มต้น",
diff --git a/packages/kilo-vscode/webview-ui/src/i18n/zh.ts b/packages/kilo-vscode/webview-ui/src/i18n/zh.ts
index ab749eb7c67..7ea0099dc29 100644
--- a/packages/kilo-vscode/webview-ui/src/i18n/zh.ts
+++ b/packages/kilo-vscode/webview-ui/src/i18n/zh.ts
@@ -230,6 +230,7 @@ export const dict = {
   "prompt.action.attachFile": "附加文件",
   "prompt.attachment.remove": "移除附件",
   "prompt.action.send": "发送",
+  "prompt.action.send.blocked": "请先回答或忽略待处理的问题",
   "prompt.action.stop": "停止",
   "prompt.action.enhance": "优化提示词",
   "prompt.action.resetModel": "重置模型为默认值",
diff --git a/packages/kilo-vscode/webview-ui/src/i18n/zht.ts b/packages/kilo-vscode/webview-ui/src/i18n/zht.ts
index 07ae7f89231..53c5b71f696 100644
--- a/packages/kilo-vscode/webview-ui/src/i18n/zht.ts
+++ b/packages/kilo-vscode/webview-ui/src/i18n/zht.ts
@@ -230,6 +230,7 @@ export const dict = {
   "prompt.action.attachFile": "附加檔案",
   "prompt.attachment.remove": "移除附件",
   "prompt.action.send": "傳送",
+  "prompt.action.send.blocked": "請先回答或忽略待處理的問題",
   "prompt.action.stop": "停止",
   "prompt.action.enhance": "改善提示詞",
   "prompt.action.resetModel": "重置模型為預設值",