Fix tray icon missing from taskbar after upgrade (#237)

apps/desktop-tauri/src-tauri/src/tray_bridge.rs

@@ -293,27 +293,36 @@ pub fn setup(app: &mut tauri::App) -> Result<(), Box<dyn std::error::Error>> {
         .build(app)?;
 
     // Apply tray promotion on startup. The NotifyIconSettings entry is created
-    // by Windows only after the icon is first registered, so on the very first
-    // run the subkey may not exist yet — apply_promotion tolerates that
-    // (returns EntryNotFound, logs a debug message). A one-time retry task is
-    // spawned so that subsequent refreshes of the icon on first-run also work.
-    let promote = codexbar::settings::Settings::load().promote_tray_icon;
-    if promote {
-        crate::tray_visibility::apply_promotion(true);
-        let app_handle = app.handle().clone();
-        tauri::async_runtime::spawn(async move {
-            tokio::time::sleep(std::time::Duration::from_secs(3)).await;
-            let still_promote = codexbar::settings::Settings::load().promote_tray_icon;
-            if still_promote {
-                crate::tray_visibility::apply_promotion(true);
-            }
-            drop(app_handle);
-        });
-    }
+    // by Windows only after the icon is first registered, so on first run /
+    // post-upgrade the subkey may not exist yet — apply_promotion tolerates
+    // EntryNotFound. Retry a few times while explorer finishes registration.
+    schedule_tray_promotion_retries(app.handle().clone());
 
     Ok(())
 }
 
+/// Re-apply Win11 tray promotion a few times after startup.
+///
+/// Windows often creates the NotifyIconSettings subkey only after the first
+/// successful NIM_ADD (and sometimes only after the icon is refreshed). A
+/// single immediate write is not enough after upgrades.
+fn schedule_tray_promotion_retries(app_handle: AppHandle) {
+    if !codexbar::settings::Settings::load().promote_tray_icon {
+        return;
+    }
+    crate::tray_visibility::apply_promotion(true);
+    tauri::async_runtime::spawn(async move {
+        for secs in [1_u64, 3, 8] {
+            tokio::time::sleep(std::time::Duration::from_secs(secs)).await;
+            if !codexbar::settings::Settings::load().promote_tray_icon {
+                break;
+            }
+            crate::tray_visibility::apply_promotion(true);
+        }
+        drop(app_handle);
+    });
+}
+
 /// Route a native menu-item click to the corresponding shell action.
 fn handle_menu_event(app: &AppHandle, id: &str) {
     match resolve_menu_action(id) {

apps/desktop-tauri/src-tauri/src/tray_visibility.rs

@@ -81,13 +81,41 @@ pub fn is_win11_build(build: u32) -> bool {
     build >= 22000
 }
 
-/// Case-insensitive path comparison after stripping trailing separators.
+/// Normalize a Windows executable path for equality checks.
+///
+/// Strips the `\\?\` / `\\?\UNC\` extended prefixes that `current_exe()` may
+/// return, unifies separators, and lowercases.
+pub fn normalize_exe_path(path: &str) -> String {
+    let mut s = path.replace('/', "\\");
+    if let Some(rest) = s.strip_prefix(r"\\?\UNC\") {
+        s = format!(r"\\{rest}");
+    } else if let Some(rest) = s.strip_prefix(r"\\?\") {
+        s = rest.to_string();
+    }
+    s.trim_end_matches('\\').to_ascii_lowercase()
+}
+
+/// Case-insensitive path comparison after stripping trailing separators and
+/// Win32 extended-length prefixes.
 /// Returns true when `entry_path` names the same executable as `exe_path`.
 pub fn matches_current_exe(entry_path: &str, exe_path: &std::path::Path) -> bool {
-    let normalize = |s: &str| s.replace('/', "\\").trim_end_matches('\\').to_ascii_lowercase();
-    let entry = normalize(entry_path);
-    let exe = normalize(&exe_path.to_string_lossy());
-    entry == exe
+    normalize_exe_path(entry_path) == normalize_exe_path(&exe_path.to_string_lossy())
+}
+
+/// True when both paths end with the same file name (case-insensitive).
+/// Used as a fallback when the full path differs after an install-dir move.
+pub fn matches_exe_file_name(entry_path: &str, exe_path: &std::path::Path) -> bool {
+    let entry_name = normalize_exe_path(entry_path)
+        .rsplit('\\')
+        .next()
+        .unwrap_or_default()
+        .to_string();
+    let exe_name = exe_path
+        .file_name()
+        .and_then(|n| n.to_str())
+        .map(normalize_exe_path)
+        .unwrap_or_default();
+    !entry_name.is_empty() && entry_name == exe_name
 }
 
 // ── Platform-specific implementation ─────────────────────────────────────────
@@ -105,9 +133,7 @@ mod windows {
     fn current_build() -> u32 {
         use winreg::enums::*;
         let hklm = RegKey::predef(HKEY_LOCAL_MACHINE);
-        let Ok(key) = hklm.open_subkey(
-            r"SOFTWARE\Microsoft\Windows NT\CurrentVersion",
-        ) else {
+        let Ok(key) = hklm.open_subkey(r"SOFTWARE\Microsoft\Windows NT\CurrentVersion") else {
             return 0;
         };
         let Ok(build_str): Result<String, _> = key.get_value("CurrentBuild") else {
@@ -128,6 +154,9 @@ mod windows {
         settings_key: &RegKey,
         exe_path: &std::path::Path,
     ) -> Result<Option<RegKey>, std::io::Error> {
+        let mut by_name: Option<RegKey> = None;
+        let mut name_matches = 0u32;
+
         for name in settings_key.enum_keys().flatten() {
             let Ok(subkey) = settings_key.open_subkey_with_flags(&name, KEY_READ | KEY_WRITE)
             else {
@@ -139,6 +168,16 @@ mod windows {
             if matches_current_exe(&entry_path, exe_path) {
                 return Ok(Some(subkey));
             }
+            if matches_exe_file_name(&entry_path, exe_path) {
+                name_matches += 1;
+                by_name = Some(subkey);
+            }
+        }
+
+        // Fallback: unique file-name match (handles install-dir moves / path
+        // rewrites where Windows still has a single CodexBar notify entry).
+        if name_matches == 1 {
+            return Ok(by_name);
         }
         Ok(None)
     }
@@ -152,8 +191,8 @@ mod windows {
         let Ok(settings_key) = hkcu.open_subkey_with_flags(NOTIFY_ICON_SETTINGS, KEY_READ) else {
             return Ok(PromotionState::EntryNotFound);
         };
-        let Some(subkey) = find_own_subkey(&settings_key, &exe_path)
-            .map_err(TrayVisibilityError::Registry)?
+        let Some(subkey) =
+            find_own_subkey(&settings_key, &exe_path).map_err(TrayVisibilityError::Registry)?
         else {
             return Ok(PromotionState::EntryNotFound);
         };
@@ -171,12 +210,13 @@ mod windows {
         }
         let exe_path = std::env::current_exe().map_err(TrayVisibilityError::ExePathUnresolvable)?;
         let hkcu = RegKey::predef(HKEY_CURRENT_USER);
-        let Ok(settings_key) = hkcu.open_subkey_with_flags(NOTIFY_ICON_SETTINGS, KEY_READ | KEY_WRITE)
+        let Ok(settings_key) =
+            hkcu.open_subkey_with_flags(NOTIFY_ICON_SETTINGS, KEY_READ | KEY_WRITE)
         else {
             return Ok(PromotionState::EntryNotFound);
         };
-        let Some(subkey) = find_own_subkey(&settings_key, &exe_path)
-            .map_err(TrayVisibilityError::Registry)?
+        let Some(subkey) =
+            find_own_subkey(&settings_key, &exe_path).map_err(TrayVisibilityError::Registry)?
         else {
             return Ok(PromotionState::EntryNotFound);
         };
@@ -209,10 +249,10 @@ mod non_windows {
     }
 }
 
-#[cfg(target_os = "windows")]
-use windows as platform;
 #[cfg(not(target_os = "windows"))]
 use non_windows as platform;
+#[cfg(target_os = "windows")]
+use windows as platform;
 
 pub fn support_status() -> TrayVisibilitySupport {
     platform::support_status()
@@ -312,6 +352,34 @@ mod tests {
         ));
     }
 
+    #[test]
+    fn matches_extended_length_prefix_from_current_exe() {
+        assert!(matches_current_exe(
+            r"C:\Users\mac\AppData\Local\Programs\CodexBar\codexbar.exe",
+            Path::new(r"\\?\C:\Users\mac\AppData\Local\Programs\CodexBar\codexbar.exe")
+        ));
+    }
+
+    #[test]
+    fn matches_exe_file_name_across_install_dirs() {
+        assert!(matches_exe_file_name(
+            r"C:\Old\CodexBar\codexbar.exe",
+            Path::new(r"C:\Users\mac\AppData\Local\Programs\CodexBar\codexbar.exe")
+        ));
+        assert!(!matches_exe_file_name(
+            r"C:\Old\CodexBar\codexbar-cli.exe",
+            Path::new(r"C:\Users\mac\AppData\Local\Programs\CodexBar\codexbar.exe")
+        ));
+    }
+
+    #[test]
+    fn normalize_strips_unc_extended_prefix() {
+        assert_eq!(
+            normalize_exe_path(r"\\?\UNC\server\share\codexbar.exe"),
+            r"\\server\share\codexbar.exe"
+        );
+    }
+
     #[test]
     fn should_write_demotion_only_when_previously_on() {
         assert!(should_write_demotion(true, false));

rust/installer/codexbar.iss

@@ -60,7 +60,12 @@ Name: "{autoprograms}\CodexBar"; Filename: "{app}\codexbar.exe"; Parameters: "me
 Name: "{autodesktop}\CodexBar"; Filename: "{app}\codexbar.exe"; Parameters: "menubar"; WorkingDir: "{app}"; Tasks: desktopicon; IconFilename: "{app}\icon.ico"
 
 [Run]
+; Interactive installs: optional checkbox on the finish page.
 Filename: "{app}\codexbar.exe"; Parameters: "menubar"; Description: "Launch CodexBar"; Flags: nowait postinstall skipifsilent; Check: CanLaunchCodexBar
+; Silent upgrades (winget / in-app updater): always relaunch so the tray icon
+; returns after CloseApplications kills the previous process. Single-instance
+; handles a second launch from the updater helper if both fire.
+Filename: "{app}\codexbar.exe"; Parameters: "menubar"; Flags: nowait postinstall skipifnotsilent; Check: CanLaunchCodexBar
 
 [Code]
 var

rust/src/settings.rs

@@ -255,7 +255,8 @@ pub struct Settings {
 
     /// Promote the tray icon out of the Windows hidden-icons overflow area.
     /// Only has effect on Windows 11 (build ≥ 22000); silently ignored elsewhere.
-    #[serde(default)]
+    /// Defaults on so upgrades keep the icon pinned to the taskbar notification area.
+    #[serde(default = "default_true")]
     pub promote_tray_icon: bool,
 }
 
@@ -447,7 +448,7 @@ impl Default for Settings {
             float_bar_dark_text: false,
             float_bar_show_reset_inline: false,
             float_bar_show_cost: false,
-            promote_tray_icon: false,
+            promote_tray_icon: true,
         }
     }
 }
@@ -475,11 +476,45 @@ impl Settings {
         #[cfg(target_os = "windows")]
         {
             settings.start_at_login = Self::sync_start_at_login_registry();
+            settings.apply_promote_tray_default_migration();
         }
 
         settings
     }
 
+    /// Marker written after the one-shot "pin tray by default" migration (issue #237).
+    fn promote_tray_default_marker_path() -> Option<PathBuf> {
+        dirs::config_dir().map(|p| p.join("CodexBar").join(".tray-pin-default-v1"))
+    }
+
+    /// Old builds defaulted `promote_tray_icon` to false and persisted that on any
+    /// settings save. Flip those installs to the new default once; later opt-outs
+    /// are preserved because the marker file remains.
+    fn should_migrate_promote_tray_default(promote_tray_icon: bool, already_migrated: bool) -> bool {
+        !already_migrated && !promote_tray_icon
+    }
+
+    fn apply_promote_tray_default_migration(&mut self) {
+        let Some(marker) = Self::promote_tray_default_marker_path() else {
+            return;
+        };
+        let already_migrated = marker.exists();
+        if Self::should_migrate_promote_tray_default(self.promote_tray_icon, already_migrated) {
+            self.promote_tray_icon = true;
+            if let Err(error) = self.save() {
+                tracing::warn!("Failed to persist promote_tray_icon default migration: {error}");
+            }
+        }
+        if !already_migrated
+            && let Some(parent) = marker.parent()
+        {
+            let _ = std::fs::create_dir_all(parent);
+            if let Err(error) = std::fs::write(&marker, b"1") {
+                tracing::warn!("Failed to write promote_tray_icon migration marker: {error}");
+            }
+        }
+    }
+
     /// Save settings to disk
     pub fn save(&self) -> anyhow::Result<()> {
         let path = Self::settings_path()

rust/src/settings/raw.rs

@@ -153,7 +153,7 @@ pub(super) struct RawSettings {
     float_bar_show_reset_inline: bool,
     #[serde(default)]
     float_bar_show_cost: bool,
-    #[serde(default)]
+    #[serde(default = "default_true")]
     promote_tray_icon: bool,
 }
 

rust/src/settings/tests.rs

@@ -12,6 +12,27 @@ fn test_settings_default() {
     assert!(!settings.show_reset_when_exhausted);
     assert!(!settings.predictive_pace_warning_enabled);
     assert!(!settings.float_bar_show_cost);
+    assert!(settings.promote_tray_icon);
+}
+
+#[test]
+fn promote_tray_icon_defaults_on_when_missing_from_disk() {
+    let loaded: Settings = serde_json::from_str(
+        r#"{
+            "enabled_providers": ["claude", "codex"],
+            "refresh_interval_secs": 300
+        }"#,
+    )
+    .expect("parse settings without promote_tray_icon");
+    assert!(loaded.promote_tray_icon);
+}
+
+#[test]
+fn promote_tray_default_migration_flips_old_false_once() {
+    assert!(Settings::should_migrate_promote_tray_default(false, false));
+    assert!(!Settings::should_migrate_promote_tray_default(true, false));
+    assert!(!Settings::should_migrate_promote_tray_default(false, true));
+    assert!(!Settings::should_migrate_promote_tray_default(true, true));
 }
 
 #[test]