diff --git a/Bloxstrap/App.xaml.cs b/Bloxstrap/App.xaml.cs
index d760390..12b62fa 100644
--- a/Bloxstrap/App.xaml.cs
+++ b/Bloxstrap/App.xaml.cs
@@ -277,7 +277,7 @@ namespace Bloxstrap
                     }
                 }
 
-                Task bootstrapperTask = Task.Run(() => bootstrapper.Run()).ContinueWith(t =>
+                Task bootstrapperTask = Task.Run(async () => await bootstrapper.Run()).ContinueWith(t =>
                 {
                     Logger.WriteLine(LOG_IDENT, "Bootstrapper task has finished");
 
diff --git a/Bloxstrap/Bootstrapper.cs b/Bloxstrap/Bootstrapper.cs
index d192b25..2edd60e 100644
--- a/Bloxstrap/Bootstrapper.cs
+++ b/Bloxstrap/Bootstrapper.cs
@@ -52,7 +52,6 @@ namespace Bloxstrap
         private readonly CancellationTokenSource _cancelTokenSource = new();
 
         private static bool FreshInstall => String.IsNullOrEmpty(App.State.Prop.VersionGuid);
-        private static string DesktopShortcutLocation => Path.Combine(Paths.Desktop, "Play Roblox.lnk");
 
         private string _playerLocation => Path.Combine(_versionFolder, "RobloxPlayerBeta.exe");
 
@@ -508,45 +507,32 @@ namespace Bloxstrap
             if (!Directory.Exists(Paths.StartMenu))
             {
                 Directory.CreateDirectory(Paths.StartMenu);
-
-                ShellLink.Shortcut.CreateShortcut(Paths.Application, "", Paths.Application, 0)
-                    .WriteToFile(Path.Combine(Paths.StartMenu, "Play Roblox.lnk"));
-
-                ShellLink.Shortcut.CreateShortcut(Paths.Application, "-menu", Paths.Application, 0)
-                    .WriteToFile(Path.Combine(Paths.StartMenu, $"{App.ProjectName} Menu.lnk"));
             }
             else
             {
                 // v2.0.0 - rebadge configuration menu as just "Bloxstrap Menu"
                 string oldMenuShortcut = Path.Combine(Paths.StartMenu, $"Configure {App.ProjectName}.lnk");
-                string newMenuShortcut = Path.Combine(Paths.StartMenu, $"{App.ProjectName} Menu.lnk");
 
                 if (File.Exists(oldMenuShortcut))
                     File.Delete(oldMenuShortcut);
-
-                if (!File.Exists(newMenuShortcut))
-                    ShellLink.Shortcut.CreateShortcut(Paths.Application, "-menu", Paths.Application, 0)
-                        .WriteToFile(newMenuShortcut);
             }
 
+            Utility.Shortcut.Create(Paths.Application, "", Path.Combine(Paths.StartMenu, "Play Roblox.lnk"));
+            Utility.Shortcut.Create(Paths.Application, "-menu", Path.Combine(Paths.StartMenu, $"{App.ProjectName} Menu.lnk"));
+
             if (App.Settings.Prop.CreateDesktopIcon)
             {
-                if (!File.Exists(DesktopShortcutLocation))
+                try
                 {
-                    try
-                    {
-                        ShellLink.Shortcut.CreateShortcut(Paths.Application, "", Paths.Application, 0)
-                            .WriteToFile(DesktopShortcutLocation);
-                    }
-                    catch (Exception ex)
-                    {
-                        App.Logger.WriteLine(LOG_IDENT, "Could not create desktop shortcut, aborting");
-                        App.Logger.WriteException(LOG_IDENT, ex);
-                    }
-                }
+                    Utility.Shortcut.Create(Paths.Application, "", Path.Combine(Paths.Desktop, "Play Roblox.lnk"));
 
-                // one-time toggle, set it back to false
-                App.Settings.Prop.CreateDesktopIcon = false;
+                    // one-time toggle, set it back to false
+                    App.Settings.Prop.CreateDesktopIcon = false;
+                }
+                catch (Exception)
+                {
+                    // suppress, we likely just don't have write perms for the desktop folder
+                }
             }
         }
 
diff --git a/Bloxstrap/Enums/AssemblyLoadStatus.cs b/Bloxstrap/Enums/AssemblyLoadStatus.cs
new file mode 100644
index 0000000..08ef104
--- /dev/null
+++ b/Bloxstrap/Enums/AssemblyLoadStatus.cs
@@ -0,0 +1,9 @@
+namespace Bloxstrap.Enums
+{
+    enum AssemblyLoadStatus
+    {
+        NotAttempted,
+        Failed,
+        Successful
+    }
+}
diff --git a/Bloxstrap/Utility/Shortcut.cs b/Bloxstrap/Utility/Shortcut.cs
new file mode 100644
index 0000000..1594a90
--- /dev/null
+++ b/Bloxstrap/Utility/Shortcut.cs
@@ -0,0 +1,43 @@
+using System.Windows;
+
+namespace Bloxstrap.Utility
+{
+    internal static class Shortcut
+    {
+        private static AssemblyLoadStatus _loadStatus = AssemblyLoadStatus.NotAttempted;
+
+        public static void Create(string exePath, string exeArgs, string lnkPath)
+        {
+            const string LOG_IDENT = "Shortcut::Create";
+
+            if (File.Exists(lnkPath))
+                return;
+
+            try
+            {
+                ShellLink.Shortcut.CreateShortcut(exePath, exeArgs, exePath, 0).WriteToFile(lnkPath);
+
+                if (_loadStatus != AssemblyLoadStatus.Successful)
+                    _loadStatus = AssemblyLoadStatus.Successful;
+            }
+            catch (Exception ex)
+            {
+                App.Logger.WriteLine(LOG_IDENT, $"Failed to create a shortcut for {lnkPath}!");
+                App.Logger.WriteException(LOG_IDENT, ex);
+
+                if (ex.GetType() != typeof(FileNotFoundException))
+                    throw;
+
+                if (_loadStatus == AssemblyLoadStatus.Failed)
+                    return;
+
+                _loadStatus = AssemblyLoadStatus.Failed;
+
+                Controls.ShowMessageBox(
+                    $"{App.ProjectName} was unable to create shortcuts for the Desktop and Start menu. They will be created the next time Roblox is launched.",
+                    MessageBoxImage.Information
+                );
+            }
+        }
+    }
+}