diff --git a/src-tauri/src/game_artwork.rs b/src-tauri/src/game_artwork.rs
index dc91910..275fcb9 100644
--- a/src-tauri/src/game_artwork.rs
+++ b/src-tauri/src/game_artwork.rs
@@ -34,8 +34,23 @@ impl ArtworkKind {
             Self::ShortcutIcon => "game shortcut icon",
         }
     }
+
+    // Windows shortcuts need .ico files, so shortcut icons are stored as ICO.
+    fn formats(self) -> &'static [ImageFormat] {
+        match self {
+            Self::Icon | Self::Banner => &ImageFormat::ALL,
+            Self::ShortcutIcon => &SHORTCUT_ICON_FORMATS,
+        }
+    }
 }
 
+const SHORTCUT_ICON_FORMATS: [ImageFormat; 4] = [
+    ImageFormat::Png,
+    ImageFormat::Jpeg,
+    ImageFormat::Webp,
+    ImageFormat::Ico,
+];
+
 #[derive(Debug, Serialize, PartialEq, Eq)]
 #[serde(rename_all = "camelCase")]
 pub(crate) struct GameArtworkResult {
@@ -281,7 +296,7 @@ fn existing_paths(
     }
 
     let mut paths = Vec::new();
-    for format in ImageFormat::ALL {
+    for &format in kind.formats() {
         let path = artwork_path(directory, game_id, format);
         match fs::symlink_metadata(&path) {
             Ok(metadata) if metadata.file_type().is_symlink() || !metadata.is_file() => {
@@ -509,6 +524,24 @@ mod tests {
         fs::remove_dir_all(root).unwrap();
     }
 
+    #[test]
+    fn shortcut_ico_is_found_by_path() {
+        let root = test_dir();
+        let store = GameArtworkStore::new(Ok(root.join("app-data")));
+        let id = "00000000-0000-0000-0000-000000000001";
+        let icon = crate::image_trim::shortcut_ico(&jpeg_image()).unwrap();
+        store.set_shortcut_icon(id, icon).unwrap();
+
+        let path = store.path(id, ArtworkKind::ShortcutIcon).unwrap().unwrap();
+        assert_eq!(
+            path,
+            root.join(format!("app-data/game-shortcut-icons/{id}.ico"))
+        );
+        store.remove(id, ArtworkKind::ShortcutIcon).unwrap();
+        assert_eq!(store.path(id, ArtworkKind::ShortcutIcon).unwrap(), None);
+        fs::remove_dir_all(root).unwrap();
+    }
+
     #[test]
     fn icon_is_persisted_and_returned_with_its_content_type() {
         let root = test_dir();
diff --git a/src-tauri/src/game_uninstall.rs b/src-tauri/src/game_uninstall.rs
index b42a614..ca456c6 100644
--- a/src-tauri/src/game_uninstall.rs
+++ b/src-tauri/src/game_uninstall.rs
@@ -152,7 +152,27 @@ pub(crate) fn is_system_directory(path: &Path) -> bool {
 /// Whether `path` lies in an operating system directory that Legio must never write to or delete.
 #[cfg(windows)]
 pub(crate) fn is_system_directory(path: &Path) -> bool {
-    std::env::var_os("SystemRoot").is_some_and(|system| path.starts_with(Path::new(&system)))
+    std::env::var_os("SystemRoot").is_some_and(|system| {
+        is_within_windows_directory(&path.to_string_lossy(), &system.to_string_lossy())
+    })
+}
+
+// Windows paths ignore case and accept both separators, which Path::starts_with does not.
+#[cfg(any(windows, test))]
+fn is_within_windows_directory(path: &str, directory: &str) -> bool {
+    let path = normalize_windows_path(path);
+    let directory = normalize_windows_path(directory);
+    path == directory
+        || path
+            .strip_prefix(&directory)
+            .is_some_and(|rest| rest.starts_with('\\'))
+}
+
+#[cfg(any(windows, test))]
+fn normalize_windows_path(path: &str) -> String {
+    path.replace('/', "\\")
+        .trim_end_matches('\\')
+        .to_lowercase()
 }
 
 fn remove_installation(
@@ -319,6 +339,28 @@ mod tests {
     use crate::database::{CreateGameInput, database_error};
     use rusqlite::params;
 
+    #[test]
+    fn system_directory_match() {
+        assert!(is_within_windows_directory(
+            r"C:\WINDOWS\System32\game.exe",
+            r"C:\Windows"
+        ));
+        assert!(is_within_windows_directory(
+            "c:/windows/system32",
+            r"C:\Windows\"
+        ));
+        assert!(is_within_windows_directory(r"C:\Windows", r"C:\WINDOWS"));
+        // Sibling directories that only share a name prefix are not system directories.
+        assert!(!is_within_windows_directory(
+            r"C:\WindowsApps\game.exe",
+            r"C:\Windows"
+        ));
+        assert!(!is_within_windows_directory(
+            r"D:\Games\Windows",
+            r"C:\Windows"
+        ));
+    }
+
     struct Fixture {
         root: PathBuf,
         directory: PathBuf,