diff --git a/src/NzbDrone.Core/Validation/Paths/StartupFolderValidator.cs b/src/NzbDrone.Core/Validation/Paths/StartupFolderValidator.cs
index 158a9ca31..9f097f8d2 100644
--- a/src/NzbDrone.Core/Validation/Paths/StartupFolderValidator.cs
+++ b/src/NzbDrone.Core/Validation/Paths/StartupFolderValidator.cs
@@ -9,7 +9,7 @@ public class StartupFolderValidator : PropertyValidator
         private readonly IAppFolderInfo _appFolderInfo;
 
         public StartupFolderValidator(IAppFolderInfo appFolderInfo)
-            : base("Path cannot be an ancestor of the start up folder")
+            : base("Path cannot be {relationship} the start up folder")
         {
             _appFolderInfo = appFolderInfo;
         }
@@ -21,7 +21,24 @@ protected override bool IsValid(PropertyValidatorContext context)
                 return true;
             }
 
-            return !_appFolderInfo.StartUpFolder.IsParentPath(context.PropertyValue.ToString());
+            var startupFolder = _appFolderInfo.StartUpFolder;
+            var folder = context.PropertyValue.ToString();
+
+            if (startupFolder.PathEquals(folder))
+            {
+                context.MessageFormatter.AppendArgument("relationship", "set to");
+
+                return false;
+            }
+
+            if (startupFolder.IsParentPath(folder))
+            {
+                context.MessageFormatter.AppendArgument("relationship", "child of");
+
+                return false;
+            }
+
+            return true;
         }
     }
 }