diff --git a/vibn-frontend/app/api/chat/route.ts b/vibn-frontend/app/api/chat/route.ts
index 10186d2..ac8080f 100644
--- a/vibn-frontend/app/api/chat/route.ts
+++ b/vibn-frontend/app/api/chat/route.ts
@@ -698,13 +698,29 @@ export async function POST(request: Request) {
           for (const tc of resp.toolCalls) {
             toolFingerprints.push(fingerprintToolCall(tc));
           }
-          // Sliding window of 10 (was 8); threshold 3 stays the same
+          // Sliding window of 10 (was 8)
           const window = toolFingerprints.slice(-10);
           const counts = new Map<string, number>();
           for (const fp of window) counts.set(fp, (counts.get(fp) ?? 0) + 1);
-          const repeated = [...counts.entries()].find(([, n]) => n >= 3);
-          if (repeated) {
-            loopBreakReason = `Repeated ${repeated[0]} ${repeated[1]}× in last 10 calls`;
+
+          // Find highest repeating tool call
+          let maxRepeats = 0;
+          let repeatedCmd = "";
+          for (const [fp, n] of counts.entries()) {
+            if (n > maxRepeats) {
+              maxRepeats = n;
+              repeatedCmd = fp.split("|")[0];
+            }
+          }
+
+          // Stage 1: Warning at 3 repeats
+          if (maxRepeats === 3) {
+            extraSystem += `\n\n[WARNING] You have called ${repeatedCmd} 3 times recently. Please wrap up this approach or try a completely different tool.`;
+          }
+
+          // Stage 2: Hard Break at 5 repeats
+          if (maxRepeats >= 5) {
+            loopBreakReason = `Repeated ${repeatedCmd} ${maxRepeats}× in last 10 calls`;
           }
 
           // Execute tool calls and add results. OpenAI-compatible APIs