diff --git a/vibn-frontend/app/api/chat/route.ts b/vibn-frontend/app/api/chat/route.ts
index 1f72d6bd..d36c28a2 100644
--- a/vibn-frontend/app/api/chat/route.ts
+++ b/vibn-frontend/app/api/chat/route.ts
@@ -272,6 +272,26 @@ ${projectsText}
 Today's date: ${new Date().toLocaleDateString("en-US", { weekday: "long", year: "numeric", month: "long", day: "numeric" })}.`;
 }
 
+function lastToolResultsHadFailure(messages: ChatMessage[], lookback = 3) {
+  const toolMsgs = messages.filter((m) => m.role === "tool").slice(-lookback);
+  for (const tm of toolMsgs) {
+    const raw = typeof tm.content === "string" ? tm.content : "";
+    try {
+      const parsed = JSON.parse(raw);
+      if (parsed.ok === false) return true;
+      if (typeof parsed.exitCode === "number" && parsed.exitCode !== 0)
+        return true;
+      if (parsed.healthCheck?.status && parsed.healthCheck.status >= 400)
+        return true;
+      if (typeof parsed.error === "string" && parsed.error.length > 0)
+        return true;
+    } catch {
+      // non-JSON result, skip
+    }
+  }
+  return false;
+}
+
 export async function POST(request: Request) {
   await ensureChatTables();
 
@@ -752,9 +772,14 @@ export async function POST(request: Request) {
           lastTurnHadTools &&
           (round >= MAX_TOOL_ROUNDS ||
             !!loopBreakReason ||
-            assistantText.trim().length === 0);
+            assistantText.trim().length === 0 ||
+            lastToolResultsHadFailure(messages));
 
         if (needsRecovery) {
+          const failureNote = lastToolResultsHadFailure(messages)
+            ? "Your last tool calls returned failures or non-2xx health checks. " +
+              "Do NOT claim those operations succeeded. "
+            : "";
           const reason = loopBreakReason
             ? `LOOP DETECTED: ${loopBreakReason}. Stop trying that approach. `
             : round >= MAX_TOOL_ROUNDS
@@ -764,7 +789,7 @@ export async function POST(request: Request) {
             const summary = await callVibnChat({
               systemPrompt:
                 systemPrompt +
-                `\n\n[RECOVERY] ${reason}Send the user 1–3 short sentences right now: (a) what you actually accomplished or learned, (b) the specific blocker (last error message verbatim if there is one), (c) what you'll try next OR a question for the user. Do NOT call any tools.`,
+                `\n\n[RECOVERY] ${reason}${failureNote}Send the user 1–3 short sentences right now: (a) what you actually accomplished or learned, (b) the specific blocker (last error message verbatim if there is one), (c) what you'll try next OR a question for the user. Do NOT call any tools.`,
               messages,
               tools: [],
               temperature: 0.3,