diff --git a/src/components/SasquatchGuide.tsx b/src/components/SasquatchGuide.tsx
index 234a798..4c2cb68 100644
--- a/src/components/SasquatchGuide.tsx
+++ b/src/components/SasquatchGuide.tsx
@@ -225,13 +225,19 @@ export function SasquatchGuide({ message, onDismiss }: SasquatchGuideProps) {
         let accumulated = '';
 
         // First pass: get AI response which may include a TOOL: call
-        // Inject system prompt as first user message if system role unsupported
-        const messagesWithSystem = [
-          { role: 'system' as const, content: SYSTEM_PROMPT },
-          ...history,
-        ];
+        // Prefix the system prompt into the first user message for compatibility
+        const historyWithContext = history.length > 0
+          ? [
+              {
+                role: 'user' as const,
+                content: `${SYSTEM_PROMPT}\n\n---\n\nUser question: ${history[0].content}`,
+              },
+              ...history.slice(1),
+            ]
+          : [{ role: 'user' as const, content: SYSTEM_PROMPT }];
+
         const firstResponse = await shakespeare.sendChatMessage(
-          messagesWithSystem,
+          historyWithContext,
           'shakespeare'
         );
 
@@ -278,12 +284,9 @@ export function SasquatchGuide({ message, onDismiss }: SasquatchGuideProps) {
             setStreamingText('');
             const toolResultStr = JSON.stringify(toolResult, null, 2);
             const secondResponse = await shakespeare.sendChatMessage([
-              { role: 'system' as const, content: SYSTEM_PROMPT },
-              ...history,
-              { role: 'assistant' as const, content: aiText },
               {
                 role: 'user' as const,
-                content: `Tool result from ${toolName}:\n${toolResultStr}\n\nNow answer the user's question naturally based on this live data. Be concise and skater-friendly.`,
+                content: `${SYSTEM_PROMPT}\n\n---\n\nUser asked: ${question}\n\nTool result from ${toolName}:\n${toolResultStr}\n\nNow answer the user's question naturally based on this live data. Be concise and skater-friendly.`,
               },
             ], 'shakespeare');