diff --git a/src-tauri/src/wsl_bridge.rs b/src-tauri/src/wsl_bridge.rs
index 0ce6121..3056305 100644
--- a/src-tauri/src/wsl_bridge.rs
+++ b/src-tauri/src/wsl_bridge.rs
@@ -1225,7 +1225,17 @@ fn process_json_line(
                         .map(|d| d.tool_use_id.clone())
                         .collect();
 
+                    // Helper function to check if a tool is a system tool that should never require permission
+                    let is_system_tool = |tool_name: &str| -> bool {
+                        matches!(tool_name, "ExitPlanMode" | "EnterPlanMode")
+                    };
+
                     for denial in denials {
+                    // Skip system tools that should never require permission
+                    if is_system_tool(&denial.tool_name) {
+                        continue;
+                    }
+
                     // Special handling for AskUserQuestion tool
                     if denial.tool_name == "AskUserQuestion" {
                         if let Some(questions) = denial