diff --git a/src/components/SasquatchGuide.tsx b/src/components/SasquatchGuide.tsx
index 0caf217..234a798 100644
--- a/src/components/SasquatchGuide.tsx
+++ b/src/components/SasquatchGuide.tsx
@@ -225,9 +225,14 @@ 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,
+        ];
         const firstResponse = await shakespeare.sendChatMessage(
-          [{ role: 'system', content: SYSTEM_PROMPT }, ...history],
-          'shakespeare/claude-sonnet-4-5'
+          messagesWithSystem,
+          'shakespeare'
         );
 
         const aiText = firstResponse.choices[0]?.message?.content as string ?? '';
@@ -273,14 +278,14 @@ export function SasquatchGuide({ message, onDismiss }: SasquatchGuideProps) {
             setStreamingText('');
             const toolResultStr = JSON.stringify(toolResult, null, 2);
             const secondResponse = await shakespeare.sendChatMessage([
-              { role: 'system', content: SYSTEM_PROMPT },
+              { role: 'system' as const, content: SYSTEM_PROMPT },
               ...history,
-              { role: 'assistant', content: aiText },
+              { role: 'assistant' as const, content: aiText },
               {
-                role: 'user',
-                content: `Tool result from ${toolName}:\n${toolResultStr}\n\nNow answer the user's question naturally based on this live data.`,
+                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.`,
               },
-            ], 'shakespeare/claude-sonnet-4-5');
+            ], 'shakespeare');
 
             accumulated = secondResponse.choices[0]?.message?.content as string ?? '';
           } catch (toolErr) {