diff --git a/WheelWizard/Features/Settings/ISettingsServices.cs b/WheelWizard/Features/Settings/ISettingsServices.cs
index 063518a3..8875fa8e 100644
--- a/WheelWizard/Features/Settings/ISettingsServices.cs
+++ b/WheelWizard/Features/Settings/ISettingsServices.cs
@@ -24,6 +24,7 @@ public interface ISettingsProperties
     Setting GAME_LOCATION { get; }
     Setting FORCE_WIIMOTE { get; }
     Setting LAUNCH_WITH_DOLPHIN { get; }
+    Setting LAUNCH_RR_ON_STARTUP { get; }
     Setting PREFERS_MODS_ROW_VIEW { get; }
     Setting FOCUSED_USER { get; }
     Setting ENABLE_ANIMATIONS { get; }
diff --git a/WheelWizard/Features/Settings/SettingsManager.cs b/WheelWizard/Features/Settings/SettingsManager.cs
index d9ae7adf..1980ad23 100644
--- a/WheelWizard/Features/Settings/SettingsManager.cs
+++ b/WheelWizard/Features/Settings/SettingsManager.cs
@@ -109,6 +109,7 @@ IFileSystem fileSystem
         GAME_LOCATION = RegisterWhWz("GameLocation", "", value => _fileSystem.File.Exists(value as string ?? string.Empty));
         FORCE_WIIMOTE = RegisterWhWz("ForceWiimote", false);
         LAUNCH_WITH_DOLPHIN = RegisterWhWz("LaunchWithDolphin", false);
+        LAUNCH_RR_ON_STARTUP = RegisterWhWz("LaunchRrOnStartup", false);
         PREFERS_MODS_ROW_VIEW = RegisterWhWz("PrefersModsRowView", true);
         FOCUSED_USER = RegisterWhWz("FavoriteUser", 0, value => (int)(value ?? -1) >= 0 && (int)(value ?? -1) < 4);
 
@@ -195,6 +196,7 @@ IFileSystem fileSystem
     public Setting GAME_LOCATION { get; }
     public Setting FORCE_WIIMOTE { get; }
     public Setting LAUNCH_WITH_DOLPHIN { get; }
+    public Setting LAUNCH_RR_ON_STARTUP { get; }
     public Setting PREFERS_MODS_ROW_VIEW { get; }
     public Setting FOCUSED_USER { get; }
     public Setting ENABLE_ANIMATIONS { get; }
diff --git a/WheelWizard/Resources/Languages/Settings.Designer.cs b/WheelWizard/Resources/Languages/Settings.Designer.cs
index 929e13f2..2a7ba89c 100644
--- a/WheelWizard/Resources/Languages/Settings.Designer.cs
+++ b/WheelWizard/Resources/Languages/Settings.Designer.cs
@@ -157,6 +157,15 @@ public static string HelperText_LaunchWithDolphin {
                 return ResourceManager.GetString("HelperText_LaunchWithDolphin", resourceCulture);
             }
         }
+
+        /// <summary>
+        ///   Looks up a localized string similar to Automatically launches Retro Rewind when Wheel Wizard starts.
+        /// </summary>
+        public static string HelperText_LaunchRrOnStartup {
+            get {
+                return ResourceManager.GetString("HelperText_LaunchRrOnStartup", resourceCulture);
+            }
+        }
         
         /// <summary>
         ///   Looks up a localized string similar to You must set these 3 paths before you can start playing Retro Rewind.
@@ -256,6 +265,15 @@ public static string Option_LaunchWithDolphin {
                 return ResourceManager.GetString("Option_LaunchWithDolphin", resourceCulture);
             }
         }
+
+        /// <summary>
+        ///   Looks up a localized string similar to Launch Retro Rewind On Startup.
+        /// </summary>
+        public static string Option_LaunchRrOnStartup {
+            get {
+                return ResourceManager.GetString("Option_LaunchRrOnStartup", resourceCulture);
+            }
+        }
         
         /// <summary>
         ///   Looks up a localized string similar to Make Primary.
diff --git a/WheelWizard/Resources/Languages/Settings.resx b/WheelWizard/Resources/Languages/Settings.resx
index f7b8a039..56d27c27 100644
--- a/WheelWizard/Resources/Languages/Settings.resx
+++ b/WheelWizard/Resources/Languages/Settings.resx
@@ -32,6 +32,9 @@
     <data name="Option_LaunchWithDolphin" xml:space="preserve">
         <value>Launch Game With Dolphin Window</value>
     </data>
+    <data name="Option_LaunchRrOnStartup" xml:space="preserve">
+        <value>Launch Retro Rewind On Startup</value>
+    </data>
     <data name="Section_Language" xml:space="preserve">
         <value>Language</value>
     </data>
@@ -44,6 +47,9 @@
     <data name="HelperText_LaunchWithDolphin" xml:space="preserve">
         <value>Will launch dolphins main window along with the game</value>
     </data>
+    <data name="HelperText_LaunchRrOnStartup" xml:space="preserve">
+        <value>Automatically launches Retro Rewind when Wheel Wizard starts</value>
+    </data>
     <data name="HelperText_ForceDisableWiimote" xml:space="preserve">
         <value>This setting disables Wiimote ingame, but enables it for the Wii channel</value>
     </data>
diff --git a/WheelWizard/Views/App.axaml.cs b/WheelWizard/Views/App.axaml.cs
index 1776bdc2..bd1c454a 100644
--- a/WheelWizard/Views/App.axaml.cs
+++ b/WheelWizard/Views/App.axaml.cs
@@ -5,6 +5,8 @@
 using Microsoft.Extensions.Logging;
 using WheelWizard.AutoUpdating;
 using WheelWizard.MiiRendering.Services;
+using WheelWizard.Settings;
+using WheelWizard.Services.Launcher;
 using WheelWizard.Services;
 using WheelWizard.Services.LiveData;
 using WheelWizard.Services.UrlProtocol;
@@ -18,6 +20,12 @@ namespace WheelWizard.Views;
 
 public class App : Application
 {
+    private enum StartupLaunchTarget
+    {
+        None,
+        RetroRewind,
+    }
+
     /// <summary>
     /// Gets the service provider configured for this application.
     /// </summary>
@@ -51,21 +59,73 @@ private void InitializeBehaviorOverrides()
         ToolTipBubbleBehavior.Initialize();
     }
 
-    private static void OpenGameBananaModWindow()
+    private static string? GetLaunchProtocolArgument()
+    {
+        var args = Environment.GetCommandLineArgs();
+        for (var i = 1; i < args.Length; i++)
+        {
+            var argument = args[i];
+            if (argument.StartsWith("wheelwizard://", StringComparison.OrdinalIgnoreCase))
+                return argument;
+        }
+
+        return null;
+    }
+
+    private static StartupLaunchTarget GetStartupLaunchTarget()
     {
         var args = Environment.GetCommandLineArgs();
+
+        for (var i = 1; i < args.Length; i++)
+        {
+            var argument = args[i];
+            if (argument.Equals("--launch", StringComparison.OrdinalIgnoreCase) || argument.Equals("-l", StringComparison.OrdinalIgnoreCase))
+            {
+                if (i + 1 >= args.Length)
+                    continue;
+
+                var launchTarget = args[++i];
+                if (launchTarget.Equals("rr", StringComparison.OrdinalIgnoreCase) ||
+                    launchTarget.Equals("retrorewind", StringComparison.OrdinalIgnoreCase) ||
+                    launchTarget.Equals("retro-rewind", StringComparison.OrdinalIgnoreCase))
+                {
+                    return StartupLaunchTarget.RetroRewind;
+                }
+
+                continue;
+            }
+
+            if (!argument.StartsWith("--launch=", StringComparison.OrdinalIgnoreCase))
+                continue;
+
+            var launchTargetFromEquals = argument["--launch=".Length..].Trim();
+            if (launchTargetFromEquals.Equals("rr", StringComparison.OrdinalIgnoreCase) ||
+                launchTargetFromEquals.Equals("retrorewind", StringComparison.OrdinalIgnoreCase) ||
+                launchTargetFromEquals.Equals("retro-rewind", StringComparison.OrdinalIgnoreCase))
+            {
+                return StartupLaunchTarget.RetroRewind;
+            }
+        }
+
+        return StartupLaunchTarget.None;
+    }
+
+    private static bool OpenGameBananaModWindow()
+    {
         ModManager.Instance.ReloadAsync();
-        if (args.Length <= 1)
-            return;
-        var protocolArgument = args[1];
+        var protocolArgument = GetLaunchProtocolArgument();
+        if (string.IsNullOrWhiteSpace(protocolArgument))
+            return false;
+
         _ = UrlProtocolManager.ShowPopupForLaunchUrlAsync(protocolArgument);
+        return true;
     }
 
     private async void OnInitializedAsync()
     {
         try
         {
-            OpenGameBananaModWindow();
+            var launchedFromProtocol = OpenGameBananaModWindow();
 
             var updateService = Services.GetRequiredService<IAutoUpdaterSingletonService>();
             var whWzDataService = Services.GetRequiredService<IWhWzDataSingletonService>();
@@ -73,6 +133,15 @@ private async void OnInitializedAsync()
             await updateService.CheckForUpdatesAsync();
             await whWzDataService.LoadBadgesAsync();
             InitializeManagers();
+
+            var settingsManager = Services.GetRequiredService<ISettingsManager>();
+            var requestedByCli = GetStartupLaunchTarget() == StartupLaunchTarget.RetroRewind;
+            var shouldLaunchRrOnStartup = !launchedFromProtocol && settingsManager.Get<bool>(settingsManager.LAUNCH_RR_ON_STARTUP);
+            if (requestedByCli || shouldLaunchRrOnStartup)
+            {
+                var rrLauncher = Services.GetRequiredService<RrLauncher>();
+                await rrLauncher.Launch();
+            }
         }
         catch (Exception e)
         {
diff --git a/WheelWizard/Views/Pages/Settings/OtherSettings.axaml b/WheelWizard/Views/Pages/Settings/OtherSettings.axaml
index dbff71f3..2460a0b0 100644
--- a/WheelWizard/Views/Pages/Settings/OtherSettings.axaml
+++ b/WheelWizard/Views/Pages/Settings/OtherSettings.axaml
@@ -34,6 +34,12 @@
                         <components1:FormFieldLabel Text="{x:Static lang:Settings.Option_LaunchWithDolphin}"
                                                    TipText="{x:Static lang:Settings.HelperText_LaunchWithDolphin}" />
                     </CheckBox>
+                    <CheckBox Margin="0,2" IsChecked="False"
+                              Classes="SwitchDark"
+                              x:Name="LaunchRrOnStartup">
+                        <components1:FormFieldLabel Text="{x:Static lang:Settings.Option_LaunchRrOnStartup}"
+                                                   TipText="{x:Static lang:Settings.HelperText_LaunchRrOnStartup}" />
+                    </CheckBox>
                 </StackPanel>
             </Border>
             
diff --git a/WheelWizard/Views/Pages/Settings/OtherSettings.axaml.cs b/WheelWizard/Views/Pages/Settings/OtherSettings.axaml.cs
index 8eb6eea4..20d10d86 100644
--- a/WheelWizard/Views/Pages/Settings/OtherSettings.axaml.cs
+++ b/WheelWizard/Views/Pages/Settings/OtherSettings.axaml.cs
@@ -31,6 +31,7 @@ public OtherSettings()
         // Attach event handlers after loading settings to avoid unwanted triggers
         DisableForce.IsCheckedChanged += ClickForceWiimote;
         LaunchWithDolphin.IsCheckedChanged += ClickLaunchWithDolphinWindow;
+        LaunchRrOnStartup.IsCheckedChanged += ClickLaunchRrOnStartup;
     }
 
     private void LoadSettings()
@@ -38,6 +39,7 @@ private void LoadSettings()
         // Only loads when the settings are not disabled (aka when the paths are set up correctly)
         DisableForce.IsChecked = SettingsService.Get<bool>(SettingsService.FORCE_WIIMOTE);
         LaunchWithDolphin.IsChecked = SettingsService.Get<bool>(SettingsService.LAUNCH_WITH_DOLPHIN);
+        LaunchRrOnStartup.IsChecked = SettingsService.Get<bool>(SettingsService.LAUNCH_RR_ON_STARTUP);
         OpenSaveFolderButton.IsEnabled = Directory.Exists(PathManager.SaveFolderPath);
     }
 
@@ -56,6 +58,11 @@ private void ClickLaunchWithDolphinWindow(object? sender, RoutedEventArgs e)
         SettingsService.Set(SettingsService.LAUNCH_WITH_DOLPHIN, LaunchWithDolphin.IsChecked == true);
     }
 
+    private void ClickLaunchRrOnStartup(object? sender, RoutedEventArgs e)
+    {
+        SettingsService.Set(SettingsService.LAUNCH_RR_ON_STARTUP, LaunchRrOnStartup.IsChecked == true);
+    }
+
     private async void Reinstall_RetroRewind(object sender, RoutedEventArgs e)
     {
         var progressWindow = new ProgressWindow();