diff --git a/MPF.Core/UI/ComboBoxItems/Element.cs b/MPF.Core/UI/ComboBoxItems/Element.cs
index 8f266045..b4568767 100644
--- a/MPF.Core/UI/ComboBoxItems/Element.cs
+++ b/MPF.Core/UI/ComboBoxItems/Element.cs
@@ -9,7 +9,7 @@ namespace MPF.Core.UI.ComboBoxItems
     /// A generic combo box element
     /// </summary>
     /// <typeparam name="T">Enum type representing the possible values</typeparam>
-    public class Element<T> : IElement where T : struct, Enum
+    public class Element<T> : IEquatable<Element<T>>, IElement where T : struct, Enum
     {
         private readonly T Data;
 
@@ -47,5 +47,18 @@ namespace MPF.Core.UI.ComboBoxItems
                 .OfType<T>()
                 .Select(e => new Element<T>(e));
         }
+
+        /// <inheritdoc/>
+#if NET48
+        public bool Equals(Element<T> other)
+#else
+        public bool Equals(Element<T>? other)
+#endif
+        {
+            if (other == null)
+                return false;
+
+            return Name == other.Name;
+        }
     }
 }
diff --git a/MPF.Core/UI/ComboBoxItems/RedumpSystemComboBoxItem.cs b/MPF.Core/UI/ComboBoxItems/RedumpSystemComboBoxItem.cs
index 4c6ea28f..d6ba20af 100644
--- a/MPF.Core/UI/ComboBoxItems/RedumpSystemComboBoxItem.cs
+++ b/MPF.Core/UI/ComboBoxItems/RedumpSystemComboBoxItem.cs
@@ -8,7 +8,7 @@ namespace MPF.Core.UI.ComboBoxItems
     /// <summary>
     /// Represents a single item in the System combo box
     /// </summary>
-    public class RedumpSystemComboBoxItem : IElement
+    public class RedumpSystemComboBoxItem : IEquatable<RedumpSystemComboBoxItem>, IElement
     {
 #if NET48
         private readonly object Data;
@@ -83,5 +83,18 @@ namespace MPF.Core.UI.ComboBoxItems
 
             return systemsValues;
         }
+
+        /// <inheritdoc/>
+#if NET48
+        public bool Equals(RedumpSystemComboBoxItem other)
+#else
+        public bool Equals(RedumpSystemComboBoxItem? other)
+#endif
+        {
+            if (other == null)
+                return false;
+
+            return Value == other.Value;
+        }
     }
 }
diff --git a/MPF.UI.Core/ElementConverter.cs b/MPF.UI.Core/ElementConverter.cs
new file mode 100644
index 00000000..e106be6e
--- /dev/null
+++ b/MPF.UI.Core/ElementConverter.cs
@@ -0,0 +1,45 @@
+using System;
+using System.Globalization;
+using System.Windows.Data;
+using MPF.Core.Data;
+using MPF.Core.UI.ComboBoxItems;
+using SabreTools.RedumpLib.Data;
+
+namespace MPF.UI.Core
+{
+    internal class ElementConverter: IValueConverter
+    {
+        public object Convert(object value, Type targetType, object parameter, CultureInfo culture)
+        {
+            switch (value)
+            {
+                case InternalProgram internalProgram:
+                    return new Element<InternalProgram>(internalProgram);
+                case RedumpSystem redumpSystem:
+                    return new RedumpSystemComboBoxItem(redumpSystem);
+
+                // Null values are treated as a system value
+                default:
+                    return new RedumpSystemComboBoxItem((RedumpSystem?)null);
+            }
+        }
+
+        public object ConvertBack(object value, Type targetType, object parameter, CultureInfo culture)
+        {
+            // If it's an IElement but ends up null
+            var element = value as IElement;
+            if (element == null)
+                return null;
+
+            switch (element)
+            {
+                case Element<InternalProgram> ipElement:
+                    return ipElement.Value;
+                case RedumpSystemComboBoxItem rsElement:
+                    return rsElement.Value;
+
+                default: return null;
+            }
+        }
+    }
+}
diff --git a/MPF.UI.Core/ViewModels/OptionsViewModel.cs b/MPF.UI.Core/ViewModels/OptionsViewModel.cs
index beed4a29..38d2067c 100644
--- a/MPF.UI.Core/ViewModels/OptionsViewModel.cs
+++ b/MPF.UI.Core/ViewModels/OptionsViewModel.cs
@@ -7,7 +7,6 @@ using System.Windows;
 using System.Windows.Forms;
 using MPF.Core.Data;
 using MPF.Core.UI.ComboBoxItems;
-using MPF.UI.Core.Windows;
 using SabreTools.RedumpLib.Web;
 using WPFCustomMessageBox;
 
@@ -25,7 +24,7 @@ namespace MPF.UI.Core.ViewModels
         /// <summary>
         /// Flag for if settings were saved or not
         /// </summary>
-        public bool SavedSettings { get; private set; }
+        public bool SavedSettings { get; internal set; }
 
         #endregion
 
@@ -51,34 +50,6 @@ namespace MPF.UI.Core.ViewModels
             Options = new Options(baseOptions);
         }
 
-        #region Load and Save
-
-        /// <summary>
-        /// Load any options-related elements
-        /// </summary>
-        /// TODO: Convert selected list item to binding
-        internal void Load(OptionsWindow parent)
-        {
-            parent.InternalProgramComboBox.SelectedIndex = InternalPrograms.FindIndex(r => r == Options.InternalProgram);
-            parent.DefaultSystemComboBox.SelectedIndex = Systems.FindIndex(r => r == Options.DefaultSystem);
-        }
-
-        /// <summary>
-        /// Save any options-related elements
-        /// </summary>
-        /// TODO: Convert selected list item to binding
-        internal void Save(OptionsWindow parent)
-        {
-            var selectedInternalProgram = parent.InternalProgramComboBox.SelectedItem as Element<InternalProgram>;
-            Options.InternalProgram = selectedInternalProgram?.Value ?? InternalProgram.DiscImageCreator;
-            var selectedDefaultSystem = parent.DefaultSystemComboBox.SelectedItem as RedumpSystemComboBoxItem;
-            Options.DefaultSystem = selectedDefaultSystem?.Value ?? null;
-
-            SavedSettings = true;
-        }
-
-        #endregion
-
         #region Population
 
         /// <summary>
@@ -158,24 +129,16 @@ namespace MPF.UI.Core.ViewModels
         /// Test Redump login credentials
         /// </summary>
 #if NET48
-        public bool? TestRedumpLogin(Window parent, string username, string password)
+        public (bool?, string) TestRedumpLogin(Window parent, string username, string password)
 #else
-        public async Task<bool?> TestRedumpLogin(Window parent, string username, string password)
+        public async Task<(bool?, string)> TestRedumpLogin(Window parent, string username, string password)
 #endif
         {
 #if NET48
-            (bool? success, string message) = RedumpWebClient.ValidateCredentials(username, password);
+            return RedumpWebClient.ValidateCredentials(username, password);
 #else
-            (bool? success, string message) = await RedumpHttpClient.ValidateCredentials(username, password);
+            return await RedumpHttpClient.ValidateCredentials(username, password);
 #endif
-            if (success == true)
-                CustomMessageBox.Show(parent, message, "Success", MessageBoxButton.OK, MessageBoxImage.Information);
-            else if (success == false)
-                CustomMessageBox.Show(parent, message, "Failure", MessageBoxButton.OK, MessageBoxImage.Error);
-            else
-                CustomMessageBox.Show(parent, message, "Error", MessageBoxButton.OK, MessageBoxImage.Error);
-
-            return success;
         }
 
         #endregion
diff --git a/MPF.UI.Core/Windows/OptionsWindow.xaml b/MPF.UI.Core/Windows/OptionsWindow.xaml
index feb7e323..1fe3626c 100644
--- a/MPF.UI.Core/Windows/OptionsWindow.xaml
+++ b/MPF.UI.Core/Windows/OptionsWindow.xaml
@@ -10,6 +10,9 @@
                         WindowStartupLocation="CenterOwner" ResizeMode="CanMinimize" SizeToContent="Height"
                         BorderBrush="DarkGray" BorderThickness="2">
 
+    <Window.Resources>
+        <core:ElementConverter x:Key="ElementConverter" />
+    </Window.Resources>
     <WindowChrome.WindowChrome>
         <WindowChrome CaptionHeight="0" ResizeBorderThickness="0" />
     </WindowChrome.WindowChrome>
@@ -99,26 +102,31 @@
                         </Grid.RowDefinitions>
 
                         <Label Grid.Row="0" Grid.Column="0" VerticalAlignment="Center" HorizontalAlignment="Right" Content="Aaru Path" />
-                        <TextBox x:Name="AaruPathTextBox" Grid.Row="0" Grid.Column="1" Height="22" HorizontalAlignment="Stretch" Text="{Binding Options.AaruPath}" VerticalContentAlignment="Center" />
+                        <TextBox x:Name="AaruPathTextBox" Grid.Row="0" Grid.Column="1" Height="22" HorizontalAlignment="Stretch"
+                                 Text="{Binding Options.AaruPath}" VerticalContentAlignment="Center" />
                         <Button x:Name="AaruPathButton" Grid.Row="0" Grid.Column="2" Height="22" Width="22" Content="..."
                                 Style="{DynamicResource CustomButtonStyle}" />
 
                         <Label Grid.Row="1" Grid.Column="0" VerticalAlignment="Center" HorizontalAlignment="Right" Content="DiscImageCreator Path" />
-                        <TextBox x:Name="DiscImageCreatorPathTextBox" Grid.Row="1" Grid.Column="1" Height="22" HorizontalAlignment="Stretch" Text="{Binding Options.DiscImageCreatorPath}" VerticalContentAlignment="Center" />
+                        <TextBox x:Name="DiscImageCreatorPathTextBox" Grid.Row="1" Grid.Column="1" Height="22" HorizontalAlignment="Stretch"
+                                 Text="{Binding Options.DiscImageCreatorPath}" VerticalContentAlignment="Center" />
                         <Button x:Name="DiscImageCreatorPathButton" Grid.Row="1" Grid.Column="2" Height="22" Width="22" Content="..."
                                 Style="{DynamicResource CustomButtonStyle}" />
 
                         <Label Grid.Row="2" Grid.Column="0" VerticalAlignment="Center" HorizontalAlignment="Right" Content="Redumper Path" />
-                        <TextBox x:Name="RedumperPathTextBox" Grid.Row="2" Grid.Column="1" Height="22" HorizontalAlignment="Stretch" Text="{Binding Options.RedumperPath}" VerticalContentAlignment="Center" />
+                        <TextBox x:Name="RedumperPathTextBox" Grid.Row="2" Grid.Column="1" Height="22" HorizontalAlignment="Stretch"
+                                 Text="{Binding Options.RedumperPath}" VerticalContentAlignment="Center" />
                         <Button x:Name="RedumperPathButton" Grid.Row="2" Grid.Column="2" Height="22" Width="22" Content="..."
                                 Style="{DynamicResource CustomButtonStyle}" />
 
                         <Label Grid.Row="3" Grid.Column="0" VerticalAlignment="Center" HorizontalAlignment="Right" Content="Default Dumping Program" />
                         <ComboBox x:Name="InternalProgramComboBox" Grid.Row="3" Grid.Column="1" Height="22" HorizontalAlignment="Stretch"
-                                  ItemsSource="{Binding InternalPrograms}" Style="{DynamicResource CustomComboBoxStyle}" />
+                                  ItemsSource="{Binding InternalPrograms}" SelectedItem="{Binding Options.InternalProgram, Converter={StaticResource ElementConverter}, Mode=TwoWay}"
+                                  Style="{DynamicResource CustomComboBoxStyle}" />
 
                         <Label Grid.Row="4" Grid.Column="0" VerticalAlignment="Center" HorizontalAlignment="Right" Content="Default Output Path" />
-                        <TextBox x:Name="DefaultOutputPathTextBox" Grid.Row="4" Grid.Column="1" Height="22" HorizontalAlignment="Stretch" Text="{Binding Options.DefaultOutputPath}" VerticalContentAlignment="Center" />
+                        <TextBox x:Name="DefaultOutputPathTextBox" Grid.Row="4" Grid.Column="1" Height="22" HorizontalAlignment="Stretch"
+                                 Text="{Binding Options.DefaultOutputPath}" VerticalContentAlignment="Center" />
                         <Button x:Name="DefaultOutputPathButton" Grid.Row="4" Grid.Column="2" Height="22" Width="22" Content="..."
                                 Style="{DynamicResource CustomButtonStyle}" />
                     </Grid>
@@ -139,7 +147,9 @@
                                      />
 
                                 <Label VerticalAlignment="Center" Content="Default System:" HorizontalAlignment="Right" />
-                                <ComboBox x:Name="DefaultSystemComboBox" Height="22" Width="200" HorizontalAlignment="Left" ItemsSource="{Binding Systems}" SelectedIndex="0" Style="{DynamicResource CustomComboBoxStyle}">
+                                <ComboBox x:Name="DefaultSystemComboBox" Height="22" Width="200" HorizontalAlignment="Left"
+                                          ItemsSource="{Binding Systems}" SelectedItem="{Binding Options.DefaultSystem, Converter={StaticResource ElementConverter}, Mode=TwoWay}"
+                                          SelectedIndex="0" Style="{DynamicResource CustomComboBoxStyle}">
                                     <ComboBox.ItemContainerStyle>
                                         <Style TargetType="{x:Type ComboBoxItem}">
                                             <Style.Triggers>
diff --git a/MPF.UI.Core/Windows/OptionsWindow.xaml.cs b/MPF.UI.Core/Windows/OptionsWindow.xaml.cs
index 3fbf4a86..89befc9a 100644
--- a/MPF.UI.Core/Windows/OptionsWindow.xaml.cs
+++ b/MPF.UI.Core/Windows/OptionsWindow.xaml.cs
@@ -1,6 +1,8 @@
 using System;
+using System.Windows;
 using MPF.Core.Data;
 using MPF.UI.Core.ViewModels;
+using WPFCustomMessageBox;
 
 namespace MPF.UI.Core.Windows
 {
@@ -34,9 +36,6 @@ namespace MPF.UI.Core.Windows
             CancelButton.Click += OnCancelClick;
             RedumpPasswordBox.PasswordChanged += OnPasswordChanged;
             RedumpLoginTestButton.Click += OnRedumpTestClick;
-
-            // Update UI with new values
-            OptionsViewModel.Load(this);
         }
 
         #region Event Handlers
@@ -52,7 +51,7 @@ namespace MPF.UI.Core.Windows
         /// </summary>
         private void OnAcceptClick(object sender, EventArgs e)
         {
-            OptionsViewModel.Save(this);
+            OptionsViewModel.SavedSettings = true;
             Close();
         }
 
@@ -60,7 +59,10 @@ namespace MPF.UI.Core.Windows
         /// Handler for CancelButtom Click event
         /// </summary>
         private void OnCancelClick(object sender, EventArgs e)
-            => Close();
+        {
+            OptionsViewModel.SavedSettings = false;
+            Close();
+        }
 
         /// <summary>
         /// Handler for 
@@ -74,12 +76,24 @@ namespace MPF.UI.Core.Windows
         /// Test Redump credentials for validity
         /// </summary>
 #if NET48
-        private void OnRedumpTestClick(object sender, EventArgs e) =>
-            OptionsViewModel.TestRedumpLogin(this, RedumpUsernameTextBox.Text, RedumpPasswordBox.Password);
+        private void OnRedumpTestClick(object sender, EventArgs e)
 #else
-        private async void OnRedumpTestClick(object sender, EventArgs e) =>
-            _ = await OptionsViewModel.TestRedumpLogin(this, RedumpUsernameTextBox.Text, RedumpPasswordBox.Password);
+        private async void OnRedumpTestClick(object sender, EventArgs e)
 #endif
+        {
+#if NET48
+            (bool? success, string message) = OptionsViewModel.TestRedumpLogin(this, RedumpUsernameTextBox.Text, RedumpPasswordBox.Password);
+#else
+            (bool? success, string message) = await OptionsViewModel.TestRedumpLogin(this, RedumpUsernameTextBox.Text, RedumpPasswordBox.Password);
+#endif
+
+            if (success == true)
+                CustomMessageBox.Show(this, message, "Success", MessageBoxButton.OK, MessageBoxImage.Information);
+            else if (success == false)
+                CustomMessageBox.Show(this, message, "Failure", MessageBoxButton.OK, MessageBoxImage.Error);
+            else
+                CustomMessageBox.Show(this, message, "Error", MessageBoxButton.OK, MessageBoxImage.Error);
+        }
 
         #endregion
     }