diff --git a/main.jai b/main.jai
index abbef4b..f79642e 100644
--- a/main.jai
+++ b/main.jai
@@ -374,15 +374,41 @@ start_singbox :: (app: *App_State) -> bool {
     }
 
     if !has_config || !has_outbounds {
+        if !url_present {
+            // Prompt configuration dialog
+            changed := show_config_url_dialog(app.hwnd, app.is_test_mode);
+            if changed {
+                // reload config to verify and fetch URL
+                config_data, read_ok := read_entire_file(config_filename);
+                if read_ok {
+                    url := get_json_string_field(config_data, "\"_url\"");
+                    if url {
+                        url_present = true;
+                    }
+                    free(config_data);
+                }
+            }
+        }
+
         if url_present {
+            // Trigger animation for downloading config
+            app.is_updating = true;
+            app.animation_frame = 0;
+            SetTimer(app.hwnd, TIMER_ANIMATION, 150, null);
+            update_tray(app);
+
             changed, success, err_msg := perform_update(app.is_test_mode);
+
+            app.is_updating = false;
+            KillTimer(app.hwnd, TIMER_ANIMATION);
+            update_tray(app);
+
             if !success {
                 msg := tprint("Could not download configuration.\nError: %", err_msg);
                 MessageBoxW(app.hwnd, utf8_to_wide(msg), utf8_to_wide("Sing-box Tray"), MB_ICONERROR);
                 return false;
             }
         } else {
-            MessageBoxW(app.hwnd, utf8_to_wide("No configuration found. Please configure the Config URL first."), utf8_to_wide("Sing-box Tray"), MB_ICONWARNING);
             return false;
         }
     }
@@ -596,11 +622,17 @@ show_context_menu :: (app: *App_State) {
 
     toggle_str := ifx app.singbox_running then "Stop Sing-box" else "Start Sing-box";
     AppendMenuW(hMenu, MF_STRING, CMD_START_STOP, utf8_to_wide(toggle_str));
-
-    AppendMenuW(hMenu, MF_STRING, CMD_SET_URL, utf8_to_wide("Configure URL..."));
-    AppendMenuW(hMenu, MF_STRING, CMD_SET_PORT, utf8_to_wide("Configure Port..."));
     AppendMenuW(hMenu, MF_STRING, CMD_UPDATE_NOW, utf8_to_wide("Update Config Now"));
 
+    hConfigureMenu := CreatePopupMenu();
+    AppendMenuW(hConfigureMenu, MF_STRING, CMD_SET_URL, utf8_to_wide("Configure URL..."));
+    AppendMenuW(hConfigureMenu, MF_STRING, CMD_SET_PORT, utf8_to_wide("Configure Port..."));
+    autostart_flags := MF_STRING;
+    if is_autostart_enabled() {
+        autostart_flags |= MF_CHECKED;
+    }
+    AppendMenuW(hConfigureMenu, autostart_flags, CMD_TOGGLE_AUTOSTART, utf8_to_wide("Start on Windows boot"));
+
     hUpdateMenu := CreatePopupMenu();
     current_interval := app.updater_data.update_interval_seconds;
     AppendMenuW(hUpdateMenu, MF_STRING | (ifx current_interval == 0 then MF_CHECKED else 0), CMD_UPDATE_NEVER, utf8_to_wide("Never"));
@@ -611,7 +643,9 @@ show_context_menu :: (app: *App_State) {
     AppendMenuW(hUpdateMenu, MF_STRING | (ifx current_interval == 86400 then MF_CHECKED else 0), CMD_UPDATE_DAILY, utf8_to_wide("Daily"));
     AppendMenuW(hUpdateMenu, MF_STRING | (ifx current_interval == 259200 then MF_CHECKED else 0), CMD_UPDATE_3D, utf8_to_wide("3 days"));
     AppendMenuW(hUpdateMenu, MF_STRING | (ifx current_interval == 604800 then MF_CHECKED else 0), CMD_UPDATE_WEEKLY, utf8_to_wide("weekly"));
-    AppendMenuW(hMenu, MF_POPUP, cast(s64) hUpdateMenu, utf8_to_wide("Config Auto-Update"));
+    AppendMenuW(hConfigureMenu, MF_POPUP, cast(s64) hUpdateMenu, utf8_to_wide("Auto-update"));
+
+    AppendMenuW(hMenu, MF_POPUP, cast(s64) hConfigureMenu, utf8_to_wide("Configure"));
 
     AppendMenuW(hMenu, MF_SEPARATOR, 0, null);
 
@@ -627,14 +661,6 @@ show_context_menu :: (app: *App_State) {
 
     AppendMenuW(hMenu, MF_SEPARATOR, 0, null);
 
-    autostart_flags := MF_STRING;
-    if is_autostart_enabled() {
-        autostart_flags |= MF_CHECKED;
-    }
-    AppendMenuW(hMenu, autostart_flags, CMD_TOGGLE_AUTOSTART, utf8_to_wide("Start on Windows boot"));
-
-    AppendMenuW(hMenu, MF_SEPARATOR, 0, null);
-
     AppendMenuW(hMenu, MF_STRING, CMD_EXIT, utf8_to_wide("Exit"));
 
     cursor_pos: POINT;
@@ -1094,9 +1120,9 @@ main :: () {
     }
     defer Shell_NotifyIconW(NIM_DELETE, *nid);
 
-    if file_exists(config_filename) {
-        start_singbox(*app_state);
-    }
+    // Try to run / start sing-box. On first start (or if config/outbounds are missing),
+    // this will prompt the configuration dialog instead of silently failing or erroring.
+    start_singbox(*app_state);
 
     SetTimer(hwnd, TIMER_PROCESS_CHECK, 1000, null);
     defer KillTimer(hwnd, TIMER_PROCESS_CHECK);