diff --git a/Bloxstrap/App.xaml.cs b/Bloxstrap/App.xaml.cs
index bc333f0e..e8a91e2e 100644
--- a/Bloxstrap/App.xaml.cs
+++ b/Bloxstrap/App.xaml.cs
@@ -198,6 +198,26 @@ protected override void OnStartup(StartupEventArgs e)
                 }
             }
 
+            if (fixInstallLocation && installLocation is not null)
+            {
+                var installer = new Installer
+                {
+                    InstallLocation = installLocation,
+                    IsImplicitInstall = true
+                };
+
+                if (installer.CheckInstallLocation())
+                {
+                    Logger.WriteLine(LOG_IDENT, $"Changing install location to '{installLocation}'");
+                    installer.DoInstall();
+                }
+                else
+                {
+                    // force reinstall
+                    installLocation = null;
+                }
+            }
+
             if (installLocation is null)
             {
                 Logger.Initialize(true);
@@ -205,21 +225,6 @@ protected override void OnStartup(StartupEventArgs e)
             }
             else
             {
-                if (fixInstallLocation)
-                {
-                    var installer = new Installer
-                    {
-                        InstallLocation = installLocation,
-                        IsImplicitInstall = true
-                    };
-
-                    if (installer.CheckInstallLocation())
-                    {
-                        Logger.WriteLine(LOG_IDENT, $"Changing install location to '{installLocation}'");
-                        installer.DoInstall();
-                    }
-                }
-
                 Paths.Initialize(installLocation);
 
                 // ensure executable is in the install directory
@@ -246,10 +251,8 @@ protected override void OnStartup(StartupEventArgs e)
 
                 Locale.Set(Settings.Prop.Locale);
 
-#if !DEBUG
                 if (!LaunchSettings.BypassUpdateCheck)
                     Installer.HandleUpgrade();
-#endif
 
                 LaunchHandler.ProcessLaunchArgs();
             }
diff --git a/Bloxstrap/LaunchSettings.cs b/Bloxstrap/LaunchSettings.cs
index 25a24fad..05ba45d9 100644
--- a/Bloxstrap/LaunchSettings.cs
+++ b/Bloxstrap/LaunchSettings.cs
@@ -28,7 +28,11 @@ public class LaunchSettings
         
         public LaunchFlag StudioFlag    { get; } = new("studio");
 
+#if DEBUG
+        public bool BypassUpdateCheck => true;
+#else
         public bool BypassUpdateCheck => UninstallFlag.Active || WatcherFlag.Active;
+#endif
 
         public LaunchMode RobloxLaunchMode { get; set; } = LaunchMode.None;