diff --git a/src/NzbDrone.Core.Test/OrganizerTests/FileNameBuilderTests/ReplaceCharacterFixture.cs b/src/NzbDrone.Core.Test/OrganizerTests/FileNameBuilderTests/ReplaceCharacterFixture.cs
new file mode 100644
index 000000000..c560c8f2d
--- /dev/null
+++ b/src/NzbDrone.Core.Test/OrganizerTests/FileNameBuilderTests/ReplaceCharacterFixture.cs
@@ -0,0 +1,88 @@
+using System.Collections.Generic;
+using System.Linq;
+using FizzWare.NBuilder;
+using FluentAssertions;
+using NUnit.Framework;
+using NzbDrone.Core.CustomFormats;
+using NzbDrone.Core.MediaFiles;
+using NzbDrone.Core.Music;
+using NzbDrone.Core.Organizer;
+using NzbDrone.Core.Qualities;
+using NzbDrone.Core.Test.Framework;
+
+namespace NzbDrone.Core.Test.OrganizerTests.FileNameBuilderTests
+{
+    [TestFixture]
+    public class ReplaceCharacterFixture : CoreTest<FileNameBuilder>
+    {
+        private Artist _artist;
+        private Album _album;
+        private AlbumRelease _release;
+        private Track _track;
+        private TrackFile _trackFiles;
+        private NamingConfig _namingConfig;
+
+        [SetUp]
+        public void Setup()
+        {
+            _artist = Builder<Artist>
+                    .CreateNew()
+                    .With(s => s.Name = "South Park")
+                    .Build();
+
+            _album = Builder<Album>
+                    .CreateNew()
+                    .With(s => s.Title = "Some Album")
+                    .Build();
+
+            _release = Builder<AlbumRelease>
+                    .CreateNew()
+                    .With(s => s.Media = new List<Medium> { new Medium { Number = 1 } })
+                    .Build();
+
+            _track = Builder<Track>.CreateNew()
+                            .With(e => e.Title = "City Sushi")
+                            .With(e => e.AbsoluteTrackNumber = 15)
+                            .With(e => e.AlbumRelease = _release)
+                            .Build();
+
+            _trackFiles = new TrackFile { Quality = new QualityModel(Quality.FLAC), ReleaseGroup = "SonarrTest" };
+
+            _namingConfig = NamingConfig.Default;
+            _namingConfig.RenameTracks = true;
+
+            Mocker.GetMock<INamingConfigService>()
+                  .Setup(c => c.GetConfig()).Returns(_namingConfig);
+
+            Mocker.GetMock<IQualityDefinitionService>()
+                .Setup(v => v.Get(Moq.It.IsAny<Quality>()))
+                .Returns<Quality>(v => Quality.DefaultQualityDefinitions.First(c => c.Quality == v));
+
+            Mocker.GetMock<ICustomFormatService>()
+                  .Setup(v => v.All())
+                  .Returns(new List<CustomFormat>());
+        }
+
+        // { "\\", "/", "<", ">", "?", "*", ":", "|", "\"" };
+        //        { "+", "+", "", "", "!", "-", " -", "", "" };
+        [TestCase("CSI: Crime Scene Investigation", "CSI - Crime Scene Investigation")]
+        [TestCase("Code:Breaker", "Code-Breaker")]
+        [TestCase("Back Slash\\", "Back Slash+")]
+        [TestCase("Forward Slash/", "Forward Slash+")]
+        [TestCase("Greater Than>", "Greater Than")]
+        [TestCase("Less Than<", "Less Than")]
+        [TestCase("Question Mark?", "Question Mark!")]
+        [TestCase("Aster*sk", "Aster-sk")]
+        [TestCase("Colon: Two Periods", "Colon - Two Periods")]
+        [TestCase("Pipe|", "Pipe")]
+        [TestCase("Quotes\"", "Quotes")]
+        public void should_replace_illegal_characters(string title, string expected)
+        {
+            _artist.Name = title;
+            _namingConfig.StandardTrackFormat = "{Artist Name}";
+
+            Subject.BuildTrackFileName(new List<Track> { _track }, _artist, _album, _trackFiles)
+                   .Should().Be(expected);
+        }
+    }
+}
diff --git a/src/NzbDrone.Core/Organizer/FileNameBuilder.cs b/src/NzbDrone.Core/Organizer/FileNameBuilder.cs
index ae3bb5b9d..757330a6f 100644
--- a/src/NzbDrone.Core/Organizer/FileNameBuilder.cs
+++ b/src/NzbDrone.Core/Organizer/FileNameBuilder.cs
@@ -249,6 +249,12 @@ namespace NzbDrone.Core.Organizer
             string[] badCharacters = { "\\", "/", "<", ">", "?", "*", ":", "|", "\"" };
             string[] goodCharacters = { "+", "+", "", "", "!", "-", "-", "", "" };
 
+            // Replace a colon followed by a space with space dash space for a better appearance
+            if (replace)
+            {
+                result = result.Replace(": ", " - ");
+            }
+
             for (int i = 0; i < badCharacters.Length; i++)
             {
                 result = result.Replace(badCharacters[i], replace ? goodCharacters[i] : string.Empty);