diff --git a/html/kidsai/script-new.js b/html/kidsai/script-new.js
index 984ac80..e47d15f 100644
--- a/html/kidsai/script-new.js
+++ b/html/kidsai/script-new.js
@@ -458,11 +458,32 @@ class KidsAIExplorer {
             // Pure "don't know" without additional thinking
             const isPureDontKnow = (hasDontKnowPhrase || isOnlyWhyQuestion || answer.trim().length < 5) && !hasSubstantialThinking && !isExpressingConfusion && !isAskingForHelp;
 
+            // Check conversation history for repeated "don't know" responses (Chat Mode)
+            const conversationHistoryChat = Array.from(this.conversationContainer.querySelectorAll('.user-message .message-content'))
+                .map(el => el.textContent.toLowerCase().trim())
+                .slice(-4); // Last 4 user responses
+            
+            console.log('🔍 Recent conversation history (Chat):', conversationHistoryChat);
+            
+            const recentDontKnowCountChat = conversationHistoryChat.filter(msg => 
+                msg.includes('weiß nicht') || msg.includes('weis nicht') || msg.includes('weiss nicht') ||
+                msg.includes("don't know") || msg.includes('i dont know') || msg.includes('keine ahnung') ||
+                msg.includes('das weiß ich nicht') || msg.includes('das weiss ich nicht') || 
+                msg.includes('das weis ich nicht') || msg.includes('weiß ich auch nicht')
+            ).length;
+            
+            console.log(`🔢 Recent "don't know" count (Chat): ${recentDontKnowCountChat}`);
+            
+            // If child has said "don't know" 2 or more times recently, they need help
+            const needsExplanationDueToRepeatedDontKnowChat = recentDontKnowCountChat >= 2;
+
             let response;
 
-            if (isExpressingConfusion) {
-                // Child is expressing confusion - provide a simple explanation
-                console.log('📤 Sending explanation request for confused child');
+            if (isExpressingConfusion || needsExplanationDueToRepeatedDontKnowChat) {
+                // Child is expressing confusion or repeatedly saying "don't know" - provide a simple explanation
+                console.log('📤 Sending explanation request for confused child or repeated dont know (Chat mode)');
+                
+                const contextReason = needsExplanationDueToRepeatedDontKnowChat ? 'repeated_dont_know' : 'confusion_explanation';
                 
                 response = await fetch('/api/respond-to-answer', {
                     method: 'POST',
@@ -474,11 +495,15 @@ class KidsAIExplorer {
                         question: currentQuestion,
                         originalTopic: originalQuestion,
                         language: this.currentLanguage,
-                        context: 'confusion_explanation',
+                        context: contextReason,
                         stepIndex: questionIndex,
-                        instructions: this.currentLanguage === 'de' 
-                            ? 'Das Kind ist verwirrt und braucht eine einfache Erklärung. Gib eine klare, konkrete Antwort für Kinder. Erkläre das Konzept mit alltäglichen Beispielen. Verwende einfache Wörter und lade zum Ausprobieren ein. Keine weiteren Fragen stellen - erst erklären!'
-                            : 'The child is confused and needs a simple explanation. Give a clear, concrete answer for children. Explain the concept with everyday examples. Use simple words and invite experimentation. Don\'t ask more questions - explain first!'
+                        instructions: needsExplanationDueToRepeatedDontKnowChat
+                            ? (this.currentLanguage === 'de' 
+                                ? 'Das Kind braucht jetzt eine einfache, klare Erklärung. Es hat bereits mehrmals "weiß nicht" gesagt. Gib eine vollständige Antwort mit praktischen Beispielen. Erkläre das Konzept Schritt für Schritt mit alltäglichen Vergleichen. Keine weiteren Fragen - das Kind braucht Wissen!'
+                                : 'The child needs a simple, clear explanation now. They have said "don\'t know" multiple times. Give a complete answer with practical examples. Explain the concept step by step with everyday comparisons. No more questions - the child needs knowledge!')
+                            : (this.currentLanguage === 'de' 
+                                ? 'Das Kind ist verwirrt und braucht eine einfache Erklärung. Gib eine klare, konkrete Antwort für Kinder. Erkläre das Konzept mit alltäglichen Beispielen. Verwende einfache Wörter und lade zum Ausprobieren ein. Keine weiteren Fragen stellen - erst erklären!'
+                                : 'The child is confused and needs a simple explanation. Give a clear, concrete answer for children. Explain the concept with everyday examples. Use simple words and invite experimentation. Don\'t ask more questions - explain first!')
                     })
                 });
             } else if (isNegative || isPureDontKnow) {
diff --git a/html/kidsai/server.js b/html/kidsai/server.js
index e919348..b263884 100755
--- a/html/kidsai/server.js
+++ b/html/kidsai/server.js
@@ -716,7 +716,8 @@ The child is asking for a definition, explanation, or clarification about locati
         console.log(`🔍 Answer analysis - isDontKnow: ${isDontKnowResponse}, answer: "${answer}"`);
         
         // If this is a "don't know" response and we're in a loop, provide explanation
-        if (isDontKnowResponse && (context === 'repeated_dont_know' || instructions.includes('mehrmals') || instructions.includes('multiple times'))) {
+        if (isDontKnowResponse && (context === 'repeated_dont_know' || 
+            (instructions && (instructions.includes('mehrmals') || instructions.includes('multiple times'))))) {
             console.log('🎯 Detected repeated "don\'t know" - providing explanation instead of more questions');
             
             const explanationPrompt = isGerman ?