diff --git a/src/NzbDrone.Core/Organizer/FileNameValidation.cs b/src/NzbDrone.Core/Organizer/FileNameValidation.cs
index e7d7235b9..ec54c73cf 100644
--- a/src/NzbDrone.Core/Organizer/FileNameValidation.cs
+++ b/src/NzbDrone.Core/Organizer/FileNameValidation.cs
@@ -1,6 +1,10 @@
+using System.Collections.Generic;
+using System.IO;
+using System.Linq;
 using System.Text.RegularExpressions;
 using FluentValidation;
 using FluentValidation.Validators;
+using NzbDrone.Common.Extensions;
 
 namespace NzbDrone.Core.Organizer
 {
@@ -12,18 +16,23 @@ namespace NzbDrone.Core.Organizer
         public static IRuleBuilderOptions<T, string> ValidTrackFormat<T>(this IRuleBuilder<T, string> ruleBuilder)
         {
             ruleBuilder.SetValidator(new NotEmptyValidator(null));
+            ruleBuilder.SetValidator(new IllegalCharactersValidator());
+
             return ruleBuilder.SetValidator(new ValidStandardTrackFormatValidator());
         }
 
         public static IRuleBuilderOptions<T, string> ValidArtistFolderFormat<T>(this IRuleBuilder<T, string> ruleBuilder)
         {
             ruleBuilder.SetValidator(new NotEmptyValidator(null));
+            ruleBuilder.SetValidator(new IllegalCharactersValidator());
+
             return ruleBuilder.SetValidator(new RegularExpressionValidator(FileNameBuilder.ArtistNameRegex)).WithMessage("Must contain Artist name");
         }
 
         public static IRuleBuilderOptions<T, string> ValidAlbumFolderFormat<T>(this IRuleBuilder<T, string> ruleBuilder)
         {
             ruleBuilder.SetValidator(new NotEmptyValidator(null));
+            ruleBuilder.SetValidator(new IllegalCharactersValidator());
             return ruleBuilder.SetValidator(new RegularExpressionValidator(FileNameBuilder.AlbumTitleRegex)).WithMessage("Must contain Album title");
 
             //.SetValidator(new RegularExpressionValidator(FileNameBuilder.ReleaseDateRegex)).WithMessage("Must contain Release year");
@@ -51,4 +60,42 @@ namespace NzbDrone.Core.Organizer
             return true;
         }
     }
+
+    public class IllegalCharactersValidator : PropertyValidator
+    {
+        private readonly char[] _invalidPathChars = Path.GetInvalidPathChars();
+
+        public IllegalCharactersValidator()
+            : base("Contains illegal characters: {InvalidCharacters}")
+        {
+
+        }
+
+        protected override bool IsValid(PropertyValidatorContext context)
+        {
+            var value = context.PropertyValue as string;
+            var invalidCharacters = new List<char>();
+
+            if (value.IsNullOrWhiteSpace())
+            {
+                return true;
+            }
+
+            foreach (var i in _invalidPathChars)
+            {
+                if (value.IndexOf(i) >= 0)
+                {
+                    invalidCharacters.Add(i);
+                }
+            }
+
+            if (invalidCharacters.Any())
+            {
+                context.MessageFormatter.AppendArgument("InvalidCharacters", string.Join("", invalidCharacters));
+                return false;
+            }
+
+            return true;
+        }
+    }
 }