diff --git a/openless-all/app/src-tauri/src/commands.rs b/openless-all/app/src-tauri/src/commands.rs
index 81511a6e..18b1923b 100644
--- a/openless-all/app/src-tauri/src/commands.rs
+++ b/openless-all/app/src-tauri/src/commands.rs
@@ -283,5 +283,52 @@ pub fn trigger_microphone_prompt(app: AppHandle) -> Result<(), String> {
 
 // ─────────────────────────── unused but exported (silences dead_code) ───────────────────────────
 
+#[tauri::command]
+pub fn is_debug_ui_key_events_enabled() -> bool {
+    std::env::var("OPENLESS_DEBUG_UI_KEY_EVENTS")
+        .ok()
+        .as_deref()
+        == Some("1")
+}
+
+#[tauri::command]
+pub fn debug_log_ui_key_event(
+    event_type: String,
+    key: String,
+    code: String,
+    ctrl: bool,
+    alt: bool,
+    shift: bool,
+    meta: bool,
+    repeat: bool,
+) {
+    if !is_debug_ui_key_events_enabled() {
+        return;
+    }
+    log::info!(
+        "[ui-key] type={} key={} code={} ctrl={} alt={} shift={} meta={} repeat={}",
+        event_type,
+        key.replace(' ', "_"),
+        code.replace(' ', "_"),
+        ctrl,
+        alt,
+        shift,
+        meta,
+        repeat
+    );
+}
+
+#[tauri::command]
+pub async fn handle_window_hotkey_event(
+    coord: CoordinatorState<'_>,
+    event_type: String,
+    key: String,
+    code: String,
+    repeat: bool,
+) -> Result<(), String> {
+    coord.handle_window_hotkey_event(&event_type, &key, &code, repeat)
+        .await
+}
+
 #[allow(dead_code)]
 fn _ensure_snapshot_used(_: CredentialsSnapshot) {}
diff --git a/openless-all/app/src-tauri/src/coordinator.rs b/openless-all/app/src-tauri/src/coordinator.rs
index c2d8c9b2..30b7e217 100644
--- a/openless-all/app/src-tauri/src/coordinator.rs
+++ b/openless-all/app/src-tauri/src/coordinator.rs
@@ -28,7 +28,7 @@ use crate::polish::{OpenAICompatibleConfig, OpenAICompatibleLLMProvider};
 use crate::recorder::Recorder;
 use crate::types::{
     CapsulePayload, CapsuleState, DictationSession, HotkeyCapability, HotkeyMode, HotkeyStatus,
-    HotkeyStatusState, InsertStatus, PolishMode,
+    HotkeyStatusState, HotkeyTrigger, InsertStatus, PolishMode,
 };
 
 #[derive(Debug, Clone, Copy, PartialEq, Eq)]
@@ -86,6 +86,7 @@ struct Inner {
     recorder: Mutex<Option<Recorder>>,
     hotkey: Mutex<Option<HotkeyMonitor>>,
     hotkey_status: Mutex<HotkeyStatus>,
+    window_hotkey_held: Mutex<bool>,
 }
 
 impl Coordinator {
@@ -109,6 +110,7 @@ impl Coordinator {
                 recorder: Mutex::new(None),
                 hotkey: Mutex::new(None),
                 hotkey_status: Mutex::new(HotkeyStatus::default()),
+                window_hotkey_held: Mutex::new(false),
             }),
         }
     }
@@ -176,6 +178,17 @@ impl Coordinator {
         Ok(())
     }
 
+    pub async fn handle_window_hotkey_event(
+        &self,
+        event_type: &str,
+        key: &str,
+        code: &str,
+        repeat: bool,
+    ) -> Result<(), String> {
+        handle_window_hotkey_event(&self.inner, event_type, key, code, repeat).await;
+        Ok(())
+    }
+
     pub async fn repolish(&self, raw_text: String, mode: PolishMode) -> Result<String, String> {
         let hotwords = enabled_phrases(&self.inner);
         polish_text(&raw_text, mode, &hotwords)
@@ -260,6 +273,87 @@ fn hotkey_bridge_loop(inner: Arc<Inner>, rx: mpsc::Receiver<HotkeyEvent>) {
     }
 }
 
+async fn handle_window_hotkey_event(
+    inner: &Arc<Inner>,
+    event_type: &str,
+    key: &str,
+    code: &str,
+    repeat: bool,
+) {
+    #[cfg(not(target_os = "windows"))]
+    {
+        let _ = (inner, event_type, key, code, repeat);
+        return;
+    }
+
+    #[cfg(target_os = "windows")]
+    {
+        if event_type == "keydown" && key == "Escape" {
+            log::info!("[window-hotkey] escape cancel from main window");
+            cancel_session(inner);
+            return;
+        }
+
+        let binding = inner.prefs.get().hotkey;
+        if !matches_window_hotkey(binding.trigger, code) {
+            return;
+        }
+
+        if event_type == "keydown" {
+            if repeat {
+                return;
+            }
+            let should_press = {
+                let mut held = inner.window_hotkey_held.lock();
+                if *held {
+                    false
+                } else {
+                    *held = true;
+                    true
+                }
+            };
+            if !should_press {
+                return;
+            }
+            log::info!(
+                "[window-hotkey] pressed trigger={:?} code={} repeat={}",
+                binding.trigger, code, repeat
+            );
+            handle_pressed(inner).await;
+        } else if event_type == "keyup" {
+            let should_release = {
+                let mut held = inner.window_hotkey_held.lock();
+                if !*held {
+                    false
+                } else {
+                    *held = false;
+                    true
+                }
+            };
+            if !should_release {
+                return;
+            }
+            log::info!(
+                "[window-hotkey] released trigger={:?} code={} repeat={}",
+                binding.trigger, code, repeat
+            );
+            handle_released(inner).await;
+        }
+    }
+}
+
+#[cfg(target_os = "windows")]
+fn matches_window_hotkey(trigger: HotkeyTrigger, code: &str) -> bool {
+    match trigger {
+        HotkeyTrigger::RightControl => code == "ControlRight",
+        HotkeyTrigger::LeftControl => code == "ControlLeft",
+        HotkeyTrigger::RightOption | HotkeyTrigger::RightAlt => code == "AltRight",
+        HotkeyTrigger::LeftOption => code == "AltLeft",
+        HotkeyTrigger::RightCommand => code == "MetaRight",
+        HotkeyTrigger::Fn => false,
+    }
+}
+
 async fn handle_pressed(inner: &Arc<Inner>) {
     let mode = inner.prefs.get().hotkey.mode;
     let phase = inner.state.lock().phase;
diff --git a/openless-all/app/src-tauri/src/lib.rs b/openless-all/app/src-tauri/src/lib.rs
index 1121287f..14318b1c 100644
--- a/openless-all/app/src-tauri/src/lib.rs
+++ b/openless-all/app/src-tauri/src/lib.rs
@@ -166,6 +166,9 @@ pub fn run() {
             commands::read_credential,
             commands::set_active_asr_provider,
             commands::set_active_llm_provider,
+            commands::is_debug_ui_key_events_enabled,
+            commands::debug_log_ui_key_event,
+            commands::handle_window_hotkey_event,
             restart_app,
         ])
         .build(tauri::generate_context!())
@@ -175,9 +178,15 @@ pub fn run() {
             RunEvent::Reopen { .. } => show_main_window(app),
             RunEvent::WindowEvent { label, event, .. } => {
                 if label == "main" {
-                    if let tauri::WindowEvent::CloseRequested { api, .. } = event {
-                        api.prevent_close();
-                        hide_main_window(app);
+                    match event {
+                        tauri::WindowEvent::Focused(focused) => {
+                            log::info!("[window] main focused={focused}");
+                        }
+                        tauri::WindowEvent::CloseRequested { api, .. } => {
+                            api.prevent_close();
+                            hide_main_window(app);
+                        }
+                        _ => {}
                     }
                 }
             }
diff --git a/openless-all/app/src/App.tsx b/openless-all/app/src/App.tsx
index f0a22e59..7814da71 100644
--- a/openless-all/app/src/App.tsx
+++ b/openless-all/app/src/App.tsx
@@ -3,7 +3,14 @@ import { Capsule } from './components/Capsule';
 import { FloatingShell } from './components/FloatingShell';
 import { Onboarding } from './components/Onboarding';
 import { detectOS } from './components/WindowChrome';
-import { checkAccessibilityPermission, checkMicrophonePermission, isTauri } from './lib/ipc';
+import {
+  checkAccessibilityPermission,
+  checkMicrophonePermission,
+  debugLogUiKeyEvent,
+  handleWindowHotkeyEvent,
+  isDebugUiKeyEventsEnabled,
+  isTauri,
+} from './lib/ipc';
 import { HotkeySettingsProvider } from './state/HotkeySettingsContext';
 
 interface AppProps {
@@ -53,6 +60,59 @@ export function App({ isCapsule }: AppProps) {
     };
   }, [os]);
 
+  useEffect(() => {
+    if (!isTauri) return;
+    let disposed = false;
+    let detach: (() => void) | null = null;
+
+    void isDebugUiKeyEventsEnabled().then(enabled => {
+      if (!enabled || disposed) return;
+      const onKeyboardEvent = (event: KeyboardEvent) => {
+        void debugLogUiKeyEvent({
+          eventType: event.type,
+          key: event.key,
+          code: event.code,
+          ctrl: event.ctrlKey,
+          alt: event.altKey,
+          shift: event.shiftKey,
+          meta: event.metaKey,
+          repeat: event.repeat,
+        });
+      };
+      window.addEventListener('keydown', onKeyboardEvent, true);
+      window.addEventListener('keyup', onKeyboardEvent, true);
+      detach = () => {
+        window.removeEventListener('keydown', onKeyboardEvent, true);
+        window.removeEventListener('keyup', onKeyboardEvent, true);
+      };
+    });
+
+    return () => {
+      disposed = true;
+      detach?.();
+    };
+  }, []);
+
+  useEffect(() => {
+    if (!isTauri || os !== 'win') return;
+
+    const onKeyboardEvent = (event: KeyboardEvent) => {
+      void handleWindowHotkeyEvent({
+        eventType: event.type,
+        key: event.key,
+        code: event.code,
+        repeat: event.repeat,
+      });
+    };
+
+    window.addEventListener('keydown', onKeyboardEvent, true);
+    window.addEventListener('keyup', onKeyboardEvent, true);
+    return () => {
+      window.removeEventListener('keydown', onKeyboardEvent, true);
+      window.removeEventListener('keyup', onKeyboardEvent, true);
+    };
+  }, [os]);
+
   if (gate === 'checking') {
     return <StartupShell />;
   }
diff --git a/openless-all/app/src/lib/ipc.ts b/openless-all/app/src/lib/ipc.ts
index 3c15c098..6dfb70cb 100644
--- a/openless-all/app/src/lib/ipc.ts
+++ b/openless-all/app/src/lib/ipc.ts
@@ -220,6 +220,54 @@ export function restartApp(): Promise<void> {
   return invokeOrMock('restart_app', undefined, () => undefined);
 }
 
+export function isDebugUiKeyEventsEnabled(): Promise<boolean> {
+  return invokeOrMock('is_debug_ui_key_events_enabled', undefined, () => false);
+}
+
+export function debugLogUiKeyEvent(payload: {
+  eventType: string;
+  key: string;
+  code: string;
+  ctrl: boolean;
+  alt: boolean;
+  shift: boolean;
+  meta: boolean;
+  repeat: boolean;
+}): Promise<void> {
+  return invokeOrMock(
+    'debug_log_ui_key_event',
+    {
+      eventType: payload.eventType,
+      key: payload.key,
+      code: payload.code,
+      ctrl: payload.ctrl,
+      alt: payload.alt,
+      shift: payload.shift,
+      meta: payload.meta,
+      repeat: payload.repeat,
+    },
+    () => undefined,
+  );
+}
+
+export function handleWindowHotkeyEvent(payload: {
+  eventType: string;
+  key: string;
+  code: string;
+  repeat: boolean;
+}): Promise<void> {
+  return invokeOrMock(
+    'handle_window_hotkey_event',
+    {
+      eventType: payload.eventType,
+      key: payload.key,
+      code: payload.code,
+      repeat: payload.repeat,
+    },
+    () => undefined,
+  );
+}
+
 export async function openExternal(url: string): Promise<void> {
   if (!isTauri) {
     window.open(url, '_blank', 'noopener,noreferrer');