diff --git a/cache.db b/cache.db
index 8e64342..ad97aac 100644
Binary files a/cache.db and b/cache.db differ
diff --git a/main.jai b/main.jai
index ab57408..c54f904 100644
--- a/main.jai
+++ b/main.jai
@@ -10,6 +10,7 @@
 
 // Custom constants
 TIMER_PROCESS_CHECK :: 1;
+TIMER_ANIMATION     :: 2;
 
 IDI_APPLICATION   :: cast(*u16) 32512;
 IDI_SHIELD        :: cast(*u16) 32518;
@@ -28,6 +29,12 @@ App_State :: struct {
 
     icon_running: HICON;
     icon_stopped: HICON;
+
+    is_connecting: bool;
+    connecting_ticks: int;
+    is_updating: bool;
+    animation_frame: int;
+    icon_frames: [4] HICON;
 }
 
 // Custom log print sending logs to OutputDebugStringW
@@ -133,7 +140,13 @@ update_tray :: (app: *App_State) {
     nid.uID = 1;
     nid.uFlags = NIF_ICON | NIF_TIP;
 
-    if app.singbox_running {
+    if app.is_connecting {
+        nid.hIcon = app.icon_frames[app.animation_frame];
+        set_tray_tip(*nid, "Sing-box: Connecting...");
+    } else if app.is_updating {
+        nid.hIcon = app.icon_frames[app.animation_frame];
+        set_tray_tip(*nid, "Sing-box: Updating Config...");
+    } else if app.singbox_running {
         nid.hIcon = app.icon_running;
         set_tray_tip(*nid, "Sing-box: Running");
     } else {
@@ -218,6 +231,11 @@ start_singbox :: (app: *App_State) -> bool {
     app.singbox_job_handle = job;
     app.singbox_running = true;
 
+    app.is_connecting = true;
+    app.connecting_ticks = 0;
+    app.animation_frame = 0;
+    SetTimer(app.hwnd, TIMER_ANIMATION, 250, null);
+
     if app.use_system_proxy {
         set_windows_system_proxy(true, tprint("127.0.0.1:%", app.port));
         log_print("System proxy enabled on port %.\n", app.port);
@@ -229,6 +247,9 @@ start_singbox :: (app: *App_State) -> bool {
 }
 
 stop_singbox :: (app: *App_State) {
+    app.is_connecting = false;
+    KillTimer(app.hwnd, TIMER_ANIMATION);
+
     if !app.singbox_running return;
 
     TerminateProcess(app.singbox_process_handle, 0);
@@ -279,7 +300,15 @@ check_process_status :: (app: *App_State) {
 }
 
 trigger_immediate_update :: (app: *App_State) {
+    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_updating = false;
+
     if success {
         if changed {
             log_print("Config updated, restarting Sing-box...\n");
@@ -293,10 +322,15 @@ trigger_immediate_update :: (app: *App_State) {
         } else {
             if !app.singbox_running {
                 start_singbox(app);
+            } else {
+                KillTimer(app.hwnd, TIMER_ANIMATION);
+                update_tray(app);
             }
             MessageBoxW(app.hwnd, utf8_to_wide("Configuration is already up-to-date."), utf8_to_wide("Sing-box Tray"), MB_ICONINFORMATION);
         }
     } else {
+        KillTimer(app.hwnd, TIMER_ANIMATION);
+        update_tray(app);
         msg := tprint("Failed to download configuration.\nError: %", err_msg);
         MessageBoxW(app.hwnd, utf8_to_wide(msg), utf8_to_wide("Sing-box Tray"), MB_ICONERROR);
     }
@@ -464,6 +498,22 @@ app_wnd_proc :: (hwnd: HWND, msg: u32, wparam: WPARAM, lparam: LPARAM) -> LRESUL
             case WM_TIMER; {
                 if wparam == TIMER_PROCESS_CHECK {
                     check_process_status(app);
+                } else if wparam == TIMER_ANIMATION {
+                    if app.is_connecting {
+                        app.connecting_ticks += 1;
+                        app.animation_frame = (app.animation_frame + 1) % 4;
+                        update_tray(app);
+                        
+                        // Stop connecting animation after 12 ticks (3 seconds at 250ms)
+                        if app.connecting_ticks >= 12 {
+                            app.is_connecting = false;
+                            KillTimer(hwnd, TIMER_ANIMATION);
+                            update_tray(app);
+                        }
+                    } else if app.is_updating {
+                        app.animation_frame = (app.animation_frame + 1) % 4;
+                        update_tray(app);
+                    }
                 }
                 return 0;
             }
@@ -504,6 +554,10 @@ main :: () {
     app_state: App_State;
     app_state.icon_running = load_stock_icon(SIID_WORLD);
     app_state.icon_stopped = load_stock_icon(SIID_ERROR);
+    app_state.icon_frames[0] = load_stock_icon(SIID_SERVER);
+    app_state.icon_frames[1] = load_stock_icon(SIID_DRIVENET);
+    app_state.icon_frames[2] = load_stock_icon(SIID_WORLD);
+    app_state.icon_frames[3] = load_stock_icon(SIID_INTERNET);
 
     hwnd := CreateWindowExW(
         0,
@@ -593,4 +647,7 @@ main :: () {
 
     if app_state.icon_running DestroyIcon(app_state.icon_running);
     if app_state.icon_stopped DestroyIcon(app_state.icon_stopped);
+    for app_state.icon_frames {
+        if it DestroyIcon(it);
+    }
 }
diff --git a/win32.jai b/win32.jai
index 9d88e67..3c236af 100644
--- a/win32.jai
+++ b/win32.jai
@@ -207,8 +207,11 @@ SHSTOCKICONINFO :: struct {
     szPath: [260] u16;
 }
 
+SIID_DRIVENET     :: 9;
 SIID_WORLD        :: 13;
+SIID_SERVER       :: 15;
 SIID_ERROR        :: 80;
+SIID_INTERNET     :: 104;
 
 SHGSI_ICON        :: 0x00000100;
 SHGSI_SMALLICON   :: 0x00000001;