diff --git a/src/extension.ts b/src/extension.ts
index e47cca3..fd9a4d0 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -1475,10 +1475,16 @@ class SidebarChatProvider implements vscode.WebviewViewProvider {
                 const internetCtx = internetEnabled 
                     ? `\n\n[CRITICAL DIRECTIVE: INTERNET ACCESS IS ENABLED]\nCurrent Time: ${new Date().toLocaleString('ko-KR')}\nYou have FULL internet access via the <read_url> tool. You MUST NEVER say you cannot search, or that your capabilities are limited. To search, ALWAYS output:\n<read_url>https://html.duckduckgo.com/html/?q=YOUR+SEARCH+TERM</read_url>\nIf the user asks to search, or asks for recent info, DO NOT apologize. Just use the tag.`
                     : '';
-                reqMessages[0] = {
-                    role: 'system',
-                    content: `${this._systemPrompt}\n\n[BACKGROUND CONTEXT]\n${contextBlock}\n${workspaceCtx}\n${brainCtx}${internetCtx}`
-                };
+                const systemContent = `${this._systemPrompt}\n\n[BACKGROUND CONTEXT]\n${contextBlock}\n${workspaceCtx}\n${brainCtx}${internetCtx}`;
+                reqMessages.shift(); // Remove system message to avoid Jinja template issues in some models
+                
+                const firstUserIdx = reqMessages.findIndex(m => m.role === 'user');
+                if (firstUserIdx >= 0) {
+                    reqMessages[firstUserIdx] = {
+                        ...reqMessages[firstUserIdx],
+                        content: `${systemContent}\n\n[USER QUERY]\n${reqMessages[firstUserIdx].content}`
+                    };
+                }
             }
 
             // Build image payload for vision models
@@ -1657,10 +1663,16 @@ class SidebarChatProvider implements vscode.WebviewViewProvider {
                 const internetCtx = internetEnabled 
                     ? `\n\n[CRITICAL DIRECTIVE: INTERNET ACCESS IS ENABLED]\nCurrent Time: ${new Date().toLocaleString('ko-KR')}\nYou have FULL internet access via the <read_url> tool. You MUST NEVER say you cannot search, or that your capabilities are limited. To search, ALWAYS output:\n<read_url>https://html.duckduckgo.com/html/?q=YOUR+SEARCH+TERM</read_url>\nIf the user asks to search, or asks for recent info, DO NOT apologize. Just use the tag.`
                     : '';
-                reqMessages[0] = {
-                    role: 'system',
-                    content: `${SYSTEM_PROMPT}\n\n[BACKGROUND CONTEXT - DO NOT EXPLAIN THIS TO THE USER UNLESS ASKED]\n${contextBlock}\n${workspaceCtx}\n${brainCtx}${internetCtx}`
-                };
+                const systemContent = `${SYSTEM_PROMPT}\n\n[BACKGROUND CONTEXT - DO NOT EXPLAIN THIS TO THE USER UNLESS ASKED]\n${contextBlock}\n${workspaceCtx}\n${brainCtx}${internetCtx}`;
+                reqMessages.shift(); // Remove system message to avoid Jinja template issues in some models
+                
+                const firstUserIdx = reqMessages.findIndex(m => m.role === 'user');
+                if (firstUserIdx >= 0) {
+                    reqMessages[firstUserIdx] = {
+                        ...reqMessages[firstUserIdx],
+                        content: `${systemContent}\n\n[USER QUERY]\n${reqMessages[firstUserIdx].content}`
+                    };
+                }
             }
 
             let isLMStudio = ollamaBase.includes('1234') || ollamaBase.includes('v1');