diff --git a/native/libwinbridge/bridge.cpp b/native/libwinbridge/bridge.cpp
index 01024c1..4aa279f 100644
--- a/native/libwinbridge/bridge.cpp
+++ b/native/libwinbridge/bridge.cpp
@@ -62,6 +62,7 @@ HWND nw = NULL;
 HWND hwnd_st_u = NULL;
 HBITMAP g_espanso_bmp = NULL;
 HICON g_espanso_ico = NULL;
+HICON g_espanso_red_ico = NULL;
 NOTIFYICONDATA nid = {};
 
 UINT WM_TASKBARCREATED = RegisterWindowMessage(L"TaskbarCreated");
@@ -309,13 +310,14 @@ LRESULT CALLBACK window_procedure(HWND window, unsigned int msg, WPARAM wp, LPAR
     }
 }
 
-int32_t initialize(void * self, wchar_t * ico_path, wchar_t * bmp_path, int32_t _show_icon) {
+int32_t initialize(void * self, wchar_t * ico_path, wchar_t * red_ico_path, wchar_t * bmp_path, int32_t _show_icon) {
     manager_instance = self;
     show_icon = _show_icon;
 
     // Load the images
     g_espanso_bmp = (HBITMAP)LoadImage(NULL, bmp_path, IMAGE_BITMAP, 0, 0, LR_LOADFROMFILE);
     g_espanso_ico = (HICON)LoadImage(NULL, ico_path, IMAGE_ICON, 0, 0, LR_DEFAULTCOLOR | LR_SHARED | LR_DEFAULTSIZE | LR_LOADFROMFILE);
+    g_espanso_red_ico = (HICON)LoadImage(NULL, red_ico_path, IMAGE_ICON, 0, 0, LR_DEFAULTCOLOR | LR_SHARED | LR_DEFAULTSIZE | LR_LOADFROMFILE);
 
     // Make the notification capable of handling different screen definitions
     SetThreadDpiAwarenessContext(DPI_AWARENESS_CONTEXT_PER_MONITOR_AWARE);
@@ -472,6 +474,19 @@ void eventloop() {
     // Something went wrong, this should have been an infinite loop.
 }
 
+void update_tray_icon(int32_t enabled) {
+    if (enabled) {
+        nid.hIcon = g_espanso_ico;
+    }else{
+        nid.hIcon = g_espanso_red_ico;
+    }
+
+    // Update the icon
+    if (show_icon) {
+        Shell_NotifyIcon(NIM_MODIFY, &nid);
+    }
+}
+
 /*
  * Type the given string simulating keyboard presses.
  */
diff --git a/native/libwinbridge/bridge.h b/native/libwinbridge/bridge.h
index f0ef9eb..7db802a 100644
--- a/native/libwinbridge/bridge.h
+++ b/native/libwinbridge/bridge.h
@@ -33,7 +33,7 @@ extern void * manager_instance;
  * Initialize the Windows parameters
  * return: 1 if OK, -1 otherwise.
  */
-extern "C" int32_t initialize(void * self, wchar_t * ico_path, wchar_t * bmp_path, int32_t show_icon);
+extern "C" int32_t initialize(void * self, wchar_t * ico_path, wchar_t * red_ico_path, wchar_t * bmp_path, int32_t show_icon);
 
 #define LEFT_VARIANT 1
 #define RIGHT_VARIANT 2
@@ -152,6 +152,11 @@ extern "C" int32_t show_notification(wchar_t * message);
  */
 extern "C" void close_notification();
 
+/*
+ * Update the tray icon status
+ */
+extern "C" void update_tray_icon(int32_t enabled);
+
 // CLIPBOARD
 
 /*
diff --git a/src/bridge/windows.rs b/src/bridge/windows.rs
index 35cec74..dd7ed32 100644
--- a/src/bridge/windows.rs
+++ b/src/bridge/windows.rs
@@ -33,6 +33,7 @@ extern "C" {
     pub fn initialize(
         s: *const c_void,
         ico_path: *const u16,
+        red_ico_path: *const u16,
         bmp_path: *const u16,
         show_icon: i32,
     ) -> i32;
@@ -48,6 +49,7 @@ extern "C" {
     pub fn register_icon_click_callback(cb: extern "C" fn(_self: *mut c_void));
     pub fn register_context_menu_click_callback(cb: extern "C" fn(_self: *mut c_void, id: i32));
     pub fn cleanup_ui();
+    pub fn update_tray_icon(enabled: i32);
 
     // CLIPBOARD
     pub fn get_clipboard(buffer: *mut u16, size: i32) -> i32;
diff --git a/src/context/mod.rs b/src/context/mod.rs
index 50805fb..cd3a5aa 100644
--- a/src/context/mod.rs
+++ b/src/context/mod.rs
@@ -48,6 +48,11 @@ pub fn new(
     macos::MacContext::new(config, send_channel, is_injecting)
 }
 
+#[cfg(target_os = "macos")]
+pub fn update_icon(enabled: bool) {
+    // TODO: add update icon on macOS
+}
+
 // LINUX IMPLEMENTATION
 #[cfg(target_os = "linux")]
 pub fn new(
@@ -58,6 +63,11 @@ pub fn new(
     linux::LinuxContext::new(config, send_channel, is_injecting)
 }
 
+#[cfg(target_os = "linux")]
+pub fn update_icon(enabled: bool) {
+    // No icon on Linux
+}
+
 // WINDOWS IMPLEMENTATION
 #[cfg(target_os = "windows")]
 pub fn new(
@@ -68,6 +78,11 @@ pub fn new(
     windows::WindowsContext::new(config, send_channel, is_injecting)
 }
 
+#[cfg(target_os = "windows")]
+pub fn update_icon(enabled: bool) {
+    windows::update_icon(enabled);
+}
+
 // espanso directories
 
 static WARING_INIT: Once = Once::new();
diff --git a/src/context/windows.rs b/src/context/windows.rs
index 07eeffa..e1cf95a 100644
--- a/src/context/windows.rs
+++ b/src/context/windows.rs
@@ -32,6 +32,7 @@ use widestring::{U16CStr, U16CString};
 
 const BMP_BINARY: &[u8] = include_bytes!("../res/win/espanso.bmp");
 const ICO_BINARY: &[u8] = include_bytes!("../res/win/espanso.ico");
+const RED_ICO_BINARY: &[u8] = include_bytes!("../res/win/espansored.ico");
 
 pub struct WindowsContext {
     send_channel: Sender<Event>,
@@ -77,8 +78,22 @@ impl WindowsContext {
             );
         }
 
+        let espanso_red_ico_image = espanso_dir.join("espansored.ico");
+        if espanso_red_ico_image.exists() {
+            info!("red ICO already initialized, skipping.");
+        } else {
+            fs::write(&espanso_red_ico_image, RED_ICO_BINARY)
+                .expect("Unable to write windows ico file");
+
+            info!(
+                "Extracted 'red ico' icon to: {}",
+                espanso_red_ico_image.to_str().unwrap_or("error")
+            );
+        }
+
         let bmp_icon = espanso_bmp_image.to_str().unwrap_or_default();
         let ico_icon = espanso_ico_image.to_str().unwrap_or_default();
+        let red_ico_icon = espanso_red_ico_image.to_str().unwrap_or_default();
 
         let send_channel = send_channel;
 
@@ -96,6 +111,7 @@ impl WindowsContext {
             register_context_menu_click_callback(context_menu_click_callback);
 
             let ico_file_c = U16CString::from_str(ico_icon).unwrap();
+            let red_ico_file_c = U16CString::from_str(red_ico_icon).unwrap();
             let bmp_file_c = U16CString::from_str(bmp_icon).unwrap();
 
             let show_icon = if config.show_icon { 1 } else { 0 };
@@ -104,6 +120,7 @@ impl WindowsContext {
             let res = initialize(
                 context_ptr,
                 ico_file_c.as_ptr(),
+                red_ico_file_c.as_ptr(),
                 bmp_file_c.as_ptr(),
                 show_icon,
             );
@@ -126,6 +143,12 @@ impl super::Context for WindowsContext {
 
 // Native bridge code
 
+pub fn update_icon(enabled: bool) {
+    unsafe {
+        crate::bridge::windows::update_tray_icon(if enabled { 1 } else { 0 });
+    }
+}
+
 extern "C" fn keypress_callback(
     _self: *mut c_void,
     raw_buffer: *const u16,
diff --git a/src/engine.rs b/src/engine.rs
index 2042fcd..3e2a534 100644
--- a/src/engine.rs
+++ b/src/engine.rs
@@ -377,6 +377,9 @@ impl<
         if config.show_notifications {
             self.ui_manager.notify(message);
         }
+
+        // Update the icon on supported OSes.
+        crate::context::update_icon(status);
     }
 
     fn on_passive(&self) {
diff --git a/src/res/win/espansored.ico b/src/res/win/espansored.ico
new file mode 100644
index 0000000..334bab0
Binary files /dev/null and b/src/res/win/espansored.ico differ