diff --git a/cache.db b/cache.db
index 51b4a12..8d6e153 100644
Binary files a/cache.db and b/cache.db differ
diff --git a/main.jai b/main.jai
index d3a2b59..fd039c9 100644
--- a/main.jai
+++ b/main.jai
@@ -229,6 +229,43 @@ file_exists :: (path: string) -> bool {
     return attribs != INVALID_FILE_ATTRIBUTES && !(attribs & FILE_ATTRIBUTE_DIRECTORY);
 }
 
+is_autostart_enabled :: () -> bool {
+    hKey: HKEY;
+    subkey := utf8_to_wide("Software\\Microsoft\\Windows\\CurrentVersion\\Run");
+    status := RegOpenKeyExW(HKEY_CURRENT_USER, subkey, 0, KEY_READ, *hKey);
+    if status != 0 return false;
+    defer RegCloseKey(hKey);
+
+    value_name := utf8_to_wide("SingboxTray");
+    
+    type: DWORD;
+    status = RegQueryValueExW(hKey, value_name, null, *type, null, null);
+    return status == 0;
+}
+
+set_autostart :: (enable: bool) -> bool {
+    hKey: HKEY;
+    subkey := utf8_to_wide("Software\\Microsoft\\Windows\\CurrentVersion\\Run");
+    status := RegOpenKeyExW(HKEY_CURRENT_USER, subkey, 0, KEY_WRITE, *hKey);
+    if status != 0 return false;
+    defer RegCloseKey(hKey);
+
+    value_name := utf8_to_wide("SingboxTray");
+
+    if enable {
+        path_buffer: [MAX_PATH] u16;
+        len := GetModuleFileNameW(null, path_buffer.data, MAX_PATH);
+        if len == 0 return false;
+
+        path_len_bytes := cast(DWORD) ((len + 1) * 2);
+        status = RegSetValueExW(hKey, value_name, 0, REG_SZ, cast(*u8) path_buffer.data, path_len_bytes);
+        return status == 0;
+    } else {
+        status = RegDeleteValueW(hKey, value_name);
+        return status == 0 || status == 2; // ERROR_FILE_NOT_FOUND is 2
+    }
+}
+
 // Hidden Process Spawning with Job Object configuration and stdout/stderr redirection
 create_process_hidden :: (cmd: string, stdout_handle: HANDLE = INVALID_HANDLE_VALUE) -> HANDLE, PROCESS_INFORMATION, bool {
     startup_info: STARTUPINFOW;
@@ -579,6 +616,14 @@ 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;
@@ -678,6 +723,21 @@ show_context_menu :: (app: *App_State) {
                 }
             }
         }
+        case CMD_TOGGLE_AUTOSTART; {
+            currently_enabled := is_autostart_enabled();
+            success := set_autostart(!currently_enabled);
+            if success {
+                new_state := !currently_enabled;
+                if new_state {
+                    log_info("Autostart on boot enabled.\n");
+                } else {
+                    log_info("Autostart on boot disabled.\n");
+                }
+            } else {
+                log_error("Failed to toggle autostart registry configuration.\n");
+                MessageBoxW(app.hwnd, utf8_to_wide("Failed to update Windows registry autostart configuration."), utf8_to_wide("Sing-box Tray"), MB_ICONERROR);
+            }
+        }
         case CMD_EXIT; {
             DestroyWindow(app.hwnd);
         }
@@ -767,6 +827,25 @@ main :: () {
     }
     global_is_test_mode = is_test;
 
+    // Change working directory to the executable's directory to resolve relative paths
+    // correctly when started via Windows autostart/registry.
+    {
+        buffer: [2048] u16;
+        len := GetModuleFileNameW(null, buffer.data, 2048);
+        if len > 0 {
+            last_backslash_idx := -1;
+            for i: 0..len-1 {
+                if buffer[i] == #char "\\" || buffer[i] == #char "/" {
+                    last_backslash_idx = i;
+                }
+            }
+            if last_backslash_idx != -1 {
+                buffer[last_backslash_idx] = 0;
+                SetCurrentDirectoryW(buffer.data);
+            }
+        }
+    }
+
     hInstance := GetModuleHandleW(null);
     class_name_str := ifx is_test then "SingboxTrayControllerClassTest" else "SingboxTrayControllerClass";
     class_name := utf8_to_wide(class_name_str);
diff --git a/win32.jai b/win32.jai
index 0c6e1d8..d63a100 100644
--- a/win32.jai
+++ b/win32.jai
@@ -82,6 +82,7 @@ CMD_EXIT            :: 1005;
 CMD_MODE_PROXY      :: 1006;
 CMD_MODE_SYS_PROXY  :: 1007;
 CMD_SET_PORT        :: 1008;
+CMD_TOGGLE_AUTOSTART:: 1009;
 
 // Boolean constants
 FALSE               :: 0;
@@ -143,6 +144,7 @@ REGSAM :: u32;
 HKEY_CURRENT_USER :: cast(HKEY) 0x80000001;
 
 KEY_WRITE     :: 0x20006;
+KEY_READ      :: 0x20019;
 
 INTERNET_OPTION_SETTINGS_CHANGED :: 39;
 INTERNET_OPTION_REFRESH          :: 37;
@@ -150,6 +152,15 @@ INTERNET_OPTION_REFRESH          :: 37;
 RegOpenKeyExW :: (hKey: HKEY, lpSubKey: LPCWSTR, ulOptions: DWORD, samDesired: REGSAM, phkResult: *HKEY) -> LSTATUS #foreign advapi32;
 RegSetValueExW :: (hKey: HKEY, lpValueName: LPCWSTR, Reserved: DWORD, dwType: DWORD, lpData: *u8, cbData: DWORD) -> LSTATUS #foreign advapi32;
 RegCloseKey :: (hKey: HKEY) -> LSTATUS #foreign advapi32;
+RegDeleteValueW :: (hKey: HKEY, lpValueName: LPCWSTR) -> LSTATUS #foreign advapi32;
+RegQueryValueExW :: (
+    hKey: HKEY,
+    lpValueName: LPCWSTR,
+    lpReserved: *DWORD,
+    lpType: *DWORD,
+    lpData: *u8,
+    lpcbData: *DWORD
+) -> LSTATUS #foreign advapi32;
 
 InternetSetOptionW :: (hInternet: HANDLE, dwOption: DWORD, lpBuffer: *void, dwBufferLength: DWORD) -> BOOL #foreign wininet;
 
@@ -265,3 +276,4 @@ set_windows_system_proxy :: (enable: bool, server: string) -> bool {
 
 
 
+