diff --git a/Wabbajack.Common/Error States/ErrorResponse.cs b/Wabbajack.Common/Error States/ErrorResponse.cs
index dd055c24..63c0abe9 100644
--- a/Wabbajack.Common/Error States/ErrorResponse.cs	
+++ b/Wabbajack.Common/Error States/ErrorResponse.cs	
@@ -77,6 +77,12 @@ namespace Wabbajack
             return new ErrorResponse(successful, reason);
         }
         #endregion
+
+        public static ErrorResponse Convert(IErrorResponse err, bool nullIsSuccess = true)
+        {
+            if (err == null) return ErrorResponse.Create(nullIsSuccess);
+            return new ErrorResponse(err.Succeeded, err.Reason, err.Exception);
+        }
     }
 
     public interface IErrorResponse
diff --git a/Wabbajack/View Models/CompilerVM.cs b/Wabbajack/View Models/CompilerVM.cs
index 6e911244..27884bf7 100644
--- a/Wabbajack/View Models/CompilerVM.cs	
+++ b/Wabbajack/View Models/CompilerVM.cs	
@@ -52,12 +52,6 @@ namespace Wabbajack
 
         public FilePickerVM DownloadLocation { get; }
 
-        [Reactive]
-        public bool ModlistLocationInError { get; set; }
-
-        [Reactive]
-        public bool DownloadLocationInError { get; set; }
-
         public IReactiveCommand BeginCommand { get; }
 
         public CompilerVM(MainWindowVM mainWindowVM, string source)
@@ -155,6 +149,14 @@ namespace Wabbajack
                 })
                 .DisposeWith(this.CompositeDisposable);
 
+            // Wire missing Mo2Folder to signal error state for Modlist Location
+            this.ModlistLocation.AdditionalError = this.WhenAny(x => x.Mo2Folder)
+                .Select<string, IErrorResponse>(moFolder =>
+                {
+                    if (Directory.Exists(moFolder)) return ErrorResponse.Success;
+                    return ErrorResponse.Fail("MO2 Folder could not be located from the given modlist location.  Make sure your modlist is inside a valid MO2 distribution.");
+                });
+
             // Load settings
             CompilationSettings settings = this.MWVM.Settings.CompilationSettings.TryCreate(source);
             this.AuthorText = settings.Author;
@@ -189,15 +191,6 @@ namespace Wabbajack
                 .DisposeWith(this.CompositeDisposable);
         }
 
-        private void ConfigureForBuild(string location)
-        {
-            var profile_folder = Path.GetDirectoryName(location);
-            if (!File.Exists(Path.Combine(this.Mo2Folder, "ModOrganizer.exe")))
-            {
-                Utils.Log($"Error! No ModOrganizer2.exe found in {this.Mo2Folder}");
-            }
-        }
-
         private async Task ExecuteBegin()
         {
             if (this.Mo2Folder != null)
diff --git a/Wabbajack/View Models/FilePickerVM.cs b/Wabbajack/View Models/FilePickerVM.cs
index 2f9aeda7..c804453f 100644
--- a/Wabbajack/View Models/FilePickerVM.cs	
+++ b/Wabbajack/View Models/FilePickerVM.cs	
@@ -46,6 +46,9 @@ namespace Wabbajack
         private readonly ObservableAsPropertyHelper<bool> _Exists;
         public bool Exists => _Exists.Value;
 
+        private readonly ObservableAsPropertyHelper<ErrorResponse> _ErrorState;
+        public ErrorResponse ErrorState => _ErrorState.Value;
+
         private readonly ObservableAsPropertyHelper<bool> _InError;
         public bool InError => _InError.Value;
 
@@ -96,15 +99,25 @@ namespace Wabbajack
                 .ObserveOn(RxApp.MainThreadScheduler)
                 .ToProperty(this, nameof(this.Exists));
 
-            this._InError = Observable.CombineLatest(
-                    this.WhenAny(x => x.Exists),
+            this._ErrorState = Observable.CombineLatest(
+                    this.WhenAny(x => x.Exists)
+                        .Select(exists => ErrorResponse.Create(successful: exists, exists ? default(string) : "Path does not exist")),
                     this.WhenAny(x => x.AdditionalError)
                         .Select(x => x ?? Observable.Return<IErrorResponse>(ErrorResponse.Success))
-                        .Switch()
-                        .Select(err => !err?.Succeeded ?? false),
-                    resultSelector: (exist, err) => !exist || err)
+                        .Switch(),
+                    resultSelector: (exist, err) =>
+                    {
+                        if (exist.Failed) return exist;
+                        return ErrorResponse.Convert(err);
+                    })
+                .ToProperty(this, nameof(this.ErrorState));
+
+            this._InError = this.WhenAny(x => x.ErrorState)
+                .Select(x => !x.Succeeded)
                 .ToProperty(this, nameof(this.InError));
 
+            // Doesn't derive from ErrorState, as we want to bubble non-empty tooltips,
+            // which is slightly different logic
             this._ErrorTooltip = Observable.CombineLatest(
                     this.WhenAny(x => x.Exists)
                         .Select(exists => exists ? default(string) : "Path does not exist"),
@@ -113,12 +126,8 @@ namespace Wabbajack
                         .Switch(),
                     resultSelector: (exists, err) =>
                     {
-                        if ((!err?.Succeeded ?? false)
-                            && !string.IsNullOrWhiteSpace(err.Reason))
-                        {
-                            return err.Reason;
-                        }
-                        return exists;
+                        if (!string.IsNullOrWhiteSpace(exists)) return exists;
+                        return err?.Reason;
                     })
                 .ToProperty(this, nameof(this.ErrorTooltip));
         }