diff --git a/AppControl Manager/App.xaml.cs b/AppControl Manager/App.xaml.cs
index 03953544f..570c47efb 100644
--- a/AppControl Manager/App.xaml.cs	
+++ b/AppControl Manager/App.xaml.cs	
@@ -6,6 +6,7 @@
 using CommunityToolkit.WinUI;
 using Microsoft.UI.Xaml;
 using Microsoft.UI.Xaml.Controls;
+using Microsoft.UI.Xaml.Media;
 using Windows.ApplicationModel;
 
 // To learn more about WinUI abd the WinUI project structure see: http://aka.ms/winui-project-info
@@ -42,6 +43,11 @@ public App()
 	{
 		this.InitializeComponent();
 
+#if DEBUG
+
+		Logger.Write("App Startup");
+#endif
+
 		// Give beautiful outline to the UI elements when using the tab key and keyboard for navigation
 		// https://learn.microsoft.com/en-us/windows/apps/design/style/reveal-focus
 		this.FocusVisualKind = FocusVisualKind.Reveal;
@@ -176,9 +182,12 @@ private async Task ShowErrorDialogAsync(Exception ex)
 				// Ensure we're on the UI thread before showing the dialog
 				await m_window.DispatcherQueue.EnqueueAsync(async () =>
 				{
+
 					ContentDialog errorDialog = new()
 					{
 						Title = "An error occurred",
+						BorderBrush = Current.Resources["AccentFillColorDefaultBrush"] as Brush ?? new SolidColorBrush(Colors.Transparent),
+						BorderThickness = new Thickness(1),
 						Content = $"An unexpected error has occurred:\n{ex.Message}",
 						CloseButtonText = "OK",
 						XamlRoot = m_window.Content.XamlRoot // Ensure dialog is attached to the main window
diff --git a/AppControl Manager/AppSettings/AppSettings.cs b/AppControl Manager/AppSettings/AppSettings.cs
index 6ba91e04b..61dd3ad21 100644
--- a/AppControl Manager/AppSettings/AppSettings.cs	
+++ b/AppControl Manager/AppSettings/AppSettings.cs	
@@ -6,14 +6,23 @@ namespace AppControlManager;
 
 internal static class AppSettings
 {
-	// Save setting to local storage with a specific key and value
+	/// <summary>
+	/// Save setting to local storage with a specific key and value
+	/// </summary>
+	/// <param name="key"></param>
+	/// <param name="value"></param>
 	internal static void SaveSetting(SettingKeys key, object? value)
 	{
 		ApplicationDataContainer localSettings = ApplicationData.Current.LocalSettings;
 		localSettings.Values[key.ToString()] = value;
 	}
 
-	// Retrieve setting from local storage with a specific key
+	/// <summary>
+	/// Retrieve setting from local storage with a specific key
+	/// </summary>
+	/// <typeparam name="T"></typeparam>
+	/// <param name="key"></param>
+	/// <returns></returns>
 	internal static T? GetSetting<T>(SettingKeys key)
 	{
 		ApplicationDataContainer localSettings = ApplicationData.Current.LocalSettings;
@@ -30,6 +39,34 @@ internal static void SaveSetting(SettingKeys key, object? value)
 	}
 
 
+	/// <summary>
+	/// Retrieve setting from local storage with a specific key and returns null if the value doesn't exist.
+	/// Used by settings that need to set a default app configuration to true/on unless there is a user-defined configuration.
+	/// </summary>
+	/// <typeparam name="T"></typeparam>
+	/// <param name="key"></param>
+	/// <returns></returns>
+	internal static T? TryGetSetting<T>(SettingKeys key)
+	{
+		ApplicationDataContainer localSettings = ApplicationData.Current.LocalSettings;
+
+		// Check if the key exists and get the value
+		if (localSettings.Values.TryGetValue(key.ToString(), out object? value))
+		{
+			// Return value cast to T (for value types, this works with nullable types as well)
+			return value is T result ? result : default;
+		}
+
+		// Return null explicitly when the key does not exist
+		// If T is a reference type, return null directly.
+		// If T is a value type, check if it supports nullable by comparing default(T?) to null.
+		// If T is not nullable (e.g., int), cast null to T? and return it, effectively providing a null result.
+		// in other words:
+		// calling it like this: AppSettings.GetSetting<bool>(AppSettings.SettingKeys.AutomaticAssignmentSidebar); and if the key doesn't exist, returns default value for bool which is false.
+		// Calling it like this: AppSettings.GetSetting<bool?>(AppSettings.SettingKeys.AutomaticAssignmentSidebar); and if the key doesn't exist, returns null.
+		return default(T?) == null ? default : (T?)(object?)null;
+	}
+
 	// Enum for the setting keys
 	// Used when saving and retrieving settings
 	internal enum SettingKeys
@@ -43,6 +80,7 @@ internal enum SettingKeys
 		MainWindowWidth,
 		MainWindowHeight,
 		MainWindowIsMaximized,
-		AutomaticAssignmentSidebar
+		AutomaticAssignmentSidebar,
+		AutoCheckForUpdateAtStartup
 	}
 }
diff --git a/AppControl Manager/MainWindow.xaml.cs b/AppControl Manager/MainWindow.xaml.cs
index 4f44ac6ef..7181193e1 100644
--- a/AppControl Manager/MainWindow.xaml.cs	
+++ b/AppControl Manager/MainWindow.xaml.cs	
@@ -291,12 +291,13 @@ static IEnumerable<NavigationViewItem> GetAllChildren(NavigationViewItem parent)
 		_ = Task.Run(() =>
 		   {
 
-			   // If AutoUpdateCheck is enabled in the user configurations, checks for updates on startup and displays a dot on the Update page in the navigation
+			   // If AutoCheckForUpdateAtStartup is enabled in the app settings, checks for updates on startup and displays a dot on the Update page in the navigation
 			   // If a new version is available.
-			   if (UserConfiguration.Get().AutoUpdateCheck == true)
+			   // Will also check for update if it's null meaning user hasn't configured the auto update check yet
+			   if (AppSettings.TryGetSetting<bool?>(AppSettings.SettingKeys.AutoCheckForUpdateAtStartup) ?? true)
 			   {
 
-				   Logger.Write("Checking for update on startup because AutoUpdateCheck is enabled");
+				   Logger.Write("Checking for update on startup");
 
 				   // Start the update check
 				   UpdateCheckResponse updateCheckResponse = updateService.Check();
@@ -1610,7 +1611,7 @@ private void RootGrid_Loaded(object sender, RoutedEventArgs e)
 		SidebarBasePolicyPathTextBox.Text = UserConfiguration.Get().UnsignedPolicyPath;
 
 		// Set the status of the sidebar toggle switch for auto assignment by getting it from saved app settings
-		AutomaticAssignmentSidebarToggleSwitch.IsOn = AppSettings.GetSetting<bool>(AppSettings.SettingKeys.AutomaticAssignmentSidebar);
+		AutomaticAssignmentSidebarToggleSwitch.IsOn = AppSettings.TryGetSetting<bool?>(AppSettings.SettingKeys.AutomaticAssignmentSidebar) ?? true;
 	}
 
 
diff --git a/AppControl Manager/Pages/Update.xaml.cs b/AppControl Manager/Pages/Update.xaml.cs
index 58f4c0b5b..411e31f6b 100644
--- a/AppControl Manager/Pages/Update.xaml.cs	
+++ b/AppControl Manager/Pages/Update.xaml.cs	
@@ -407,10 +407,14 @@ await Task.Run(() =>
 	}
 
 
-	// Event handler for the Auto Update Check Toggle Button to modify the User Configurations file
+	/// <summary>
+	/// Event handler for the Auto Update Check Toggle Button to modify the app settings
+	/// </summary>
+	/// <param name="sender"></param>
+	/// <param name="e"></param>
 	private void AutoUpdateCheckToggle_Toggled(object sender, RoutedEventArgs e)
 	{
-		_ = UserConfiguration.Set(AutoUpdateCheck: AutoUpdateCheckToggle.IsOn);
+		AppSettings.SaveSetting(AppSettings.SettingKeys.AutoCheckForUpdateAtStartup, AutoUpdateCheckToggle.IsOn);
 	}
 
 
@@ -425,8 +429,8 @@ protected override void OnNavigatedTo(NavigationEventArgs e)
 		// Call the base class implementation first
 		base.OnNavigatedTo(e);
 
-		// Set the toggle for Auto Update Check based on the User Configurations
-		AutoUpdateCheckToggle.IsOn = (UserConfiguration.Get().AutoUpdateCheck == true);
+		// Set the toggle for Auto Update Check based on app settings
+		AutoUpdateCheckToggle.IsOn = AppSettings.TryGetSetting<bool?>(AppSettings.SettingKeys.AutoCheckForUpdateAtStartup) ?? true;
 
 		// Grab the latest text for the CheckForUpdateButton button
 		CheckForUpdateButton.Content = GlobalVars.updateButtonTextOnTheUpdatePage;
@@ -451,9 +455,9 @@ private void HardenedUpdateProcedureToggle_Toggled(object sender, RoutedEventArg
 	/// <param name="e"></param>
 	private void AutoUpdateCheckToggleSettingsCard_Click(object sender, RoutedEventArgs e)
 	{
-		_ = UserConfiguration.Set(AutoUpdateCheck: AutoUpdateCheckToggle.IsOn);
-
 		AutoUpdateCheckToggle.IsOn = !AutoUpdateCheckToggle.IsOn;
+
+		AppSettings.SaveSetting(AppSettings.SettingKeys.AutoCheckForUpdateAtStartup, AutoUpdateCheckToggle.IsOn);
 	}