diff --git a/DICUI/MainWindow.xaml.cs b/DICUI/MainWindow.xaml.cs
index ce2553e3..61cb901e 100644
--- a/DICUI/MainWindow.xaml.cs
+++ b/DICUI/MainWindow.xaml.cs
@@ -354,7 +354,7 @@ namespace DICUI
         /// <returns>Filled DumpEnvironment instance</returns>
         private DumpEnvironment DetermineEnvironment()
         {
-            return new DumpEnvironment()
+            var env = new DumpEnvironment()
             {
                 // Paths to tools
                 SubdumpPath = _options.SubDumpPath,
@@ -376,6 +376,9 @@ namespace DICUI
                 System = SystemTypeComboBox.SelectedItem as KnownSystemComboBoxItem,
                 Type = MediaTypeComboBox.SelectedItem as MediaType?
             };
+
+            env.FixOutputPaths();
+            return env;
         }
 
         /// <summary>
diff --git a/DICUI/Utilities/DumpEnvironment.cs b/DICUI/Utilities/DumpEnvironment.cs
index 15f1edec..430c2a86 100644
--- a/DICUI/Utilities/DumpEnvironment.cs
+++ b/DICUI/Utilities/DumpEnvironment.cs
@@ -187,6 +187,8 @@ namespace DICUI.Utilities
                 if (Drive == null)
                     return null;
 
+                FixOutputPaths();
+
                 // Set the proper parameters
                 DICParameters = new Parameters(System, Type, Drive.Letter, Path.Combine(OutputDirectory, OutputFilename), driveSpeed, ParanoidMode, RereadAmountC2);
                 if (QuietMode)