diff --git a/src/Files.App/Services/Windows/WindowsJumpListService.cs b/src/Files.App/Services/Windows/WindowsJumpListService.cs
index 5c1c8b9d1abb..572718c619d1 100644
--- a/src/Files.App/Services/Windows/WindowsJumpListService.cs
+++ b/src/Files.App/Services/Windows/WindowsJumpListService.cs
@@ -79,7 +79,8 @@ public async Task RefreshPinnedFoldersAsync()
 		{
 			try
 			{
-				App.QuickAccessManager.PinnedItemsWatcher.EnableRaisingEvents = false;
+				if (App.QuickAccessManager.PinnedItemsWatcher is not null)
+					App.QuickAccessManager.PinnedItemsWatcher.EnableRaisingEvents = false;
 
 				if (JumpList.IsSupported())
 				{
@@ -101,7 +102,8 @@ public async Task RefreshPinnedFoldersAsync()
 			}
 			finally
 			{
-				SafetyExtensions.IgnoreExceptions(() => App.QuickAccessManager.PinnedItemsWatcher.EnableRaisingEvents = true);
+				if (App.QuickAccessManager.PinnedItemsWatcher is not null)
+					SafetyExtensions.IgnoreExceptions(() => App.QuickAccessManager.PinnedItemsWatcher.EnableRaisingEvents = true);
 			}
 		}
 
diff --git a/src/Files.App/Services/Windows/WindowsQuickAccessService.cs b/src/Files.App/Services/Windows/WindowsQuickAccessService.cs
index b060f123a4d0..5273ce93b0da 100644
--- a/src/Files.App/Services/Windows/WindowsQuickAccessService.cs
+++ b/src/Files.App/Services/Windows/WindowsQuickAccessService.cs
@@ -95,13 +95,15 @@ public async Task SaveAsync(string[] items)
 			if (Equals(items, App.QuickAccessManager.Model.PinnedFolders.ToArray()))
 				return;
 
-			App.QuickAccessManager.PinnedItemsWatcher.EnableRaisingEvents = false;
+			if (App.QuickAccessManager.PinnedItemsWatcher is not null)
+				App.QuickAccessManager.PinnedItemsWatcher.EnableRaisingEvents = false;
 
 			// Unpin every item that is below this index and then pin them all in order
 			await UnpinFromSidebarAsync([], false);
 
 			await PinToSidebarAsync(items, false);
-			App.QuickAccessManager.PinnedItemsWatcher.EnableRaisingEvents = true;
+			if (App.QuickAccessManager.PinnedItemsWatcher is not null)
+				App.QuickAccessManager.PinnedItemsWatcher.EnableRaisingEvents = true;
 
 			App.QuickAccessManager.UpdateQuickAccessWidget?.Invoke(this, new ModifyQuickAccessEventArgs(items, true)
 			{
diff --git a/src/Files.App/Utils/Global/QuickAccessManager.cs b/src/Files.App/Utils/Global/QuickAccessManager.cs
index 5971690c42b5..6b2b1de36bd6 100644
--- a/src/Files.App/Utils/Global/QuickAccessManager.cs
+++ b/src/Files.App/Utils/Global/QuickAccessManager.cs
@@ -25,14 +25,27 @@ public QuickAccessManager()
 
 		public void Initialize()
 		{
-			PinnedItemsWatcher = new()
+			var automaticDestinationsPath = Path.Join(Environment.GetFolderPath(Environment.SpecialFolder.ApplicationData), "Microsoft", "Windows", "Recent", "AutomaticDestinations");
+			
+			// Only initialize FileSystemWatcher if the directory exists
+			// This handles cases where AppData is redirected to network locations that don't contain Windows system directories
+			if (Directory.Exists(automaticDestinationsPath))
 			{
-				Path = Path.Join(Environment.GetFolderPath(Environment.SpecialFolder.ApplicationData), "Microsoft", "Windows", "Recent", "AutomaticDestinations"),
-				Filter = "f01b4d95cf55d32a.automaticDestinations-ms",
-				NotifyFilter = NotifyFilters.LastAccess | NotifyFilters.LastWrite | NotifyFilters.FileName
-			};
-
-			PinnedItemsWatcher.Changed += PinnedItemsWatcher_Changed;
+				PinnedItemsWatcher = new()
+				{
+					Path = automaticDestinationsPath,
+					Filter = "f01b4d95cf55d32a.automaticDestinations-ms",
+					NotifyFilter = NotifyFilters.LastAccess | NotifyFilters.LastWrite | NotifyFilters.FileName
+				};
+
+				PinnedItemsWatcher.Changed += PinnedItemsWatcher_Changed;
+			}
+			else
+			{
+				// If the directory doesn't exist (e.g., redirected AppData), skip FileSystemWatcher initialization
+				// The app will still function, but won't receive automatic updates when pinned items change externally
+				PinnedItemsWatcher = null;
+			}
 		}
 
 		private void PinnedItemsWatcher_Changed(object sender, FileSystemEventArgs e)