diff --git a/frontend/src/Settings/MediaManagement/Naming/Naming.js b/frontend/src/Settings/MediaManagement/Naming/Naming.js
index 1cd6c16c7..5f7ccf19a 100644
--- a/frontend/src/Settings/MediaManagement/Naming/Naming.js
+++ b/frontend/src/Settings/MediaManagement/Naming/Naming.js
@@ -120,6 +120,7 @@ class Naming extends Component {
     } = this.state;
 
     const renameEpisodes = hasSettings && settings.renameEpisodes.value;
+    const replaceIllegalCharacters = hasSettings && settings.replaceIllegalCharacters.value;
 
     const multiEpisodeStyleOptions = [
       { key: 0, value: 'Extend', hint: 'S01E01-02-03' },
@@ -130,6 +131,14 @@ class Naming extends Component {
       { key: 5, value: 'Prefixed Range', hint: 'S01E01-E03' }
     ];
 
+    const colonReplacementOptions = [
+      { key: 0, value: 'Delete' },
+      { key: 1, value: 'Replace with Dash' },
+      { key: 2, value: 'Replace with Space Dash' },
+      { key: 3, value: 'Replace with Space Dash Space' },
+      { key: 4, value: 'Smart Replace', hint: 'Dash or Space Dash depending on name' }
+    ];
+
     const standardEpisodeFormatHelpTexts = [];
     const standardEpisodeFormatErrors = [];
     const dailyEpisodeFormatHelpTexts = [];
@@ -232,6 +241,22 @@ class Naming extends Component {
                 />
               </FormGroup>
 
+              {
+                replaceIllegalCharacters ?
+                  <FormGroup>
+                    <FormLabel>Colon Replacement</FormLabel>
+
+                    <FormInputGroup
+                      type={inputTypes.SELECT}
+                      name="colonReplacementFormat"
+                      values={colonReplacementOptions}
+                      onChange={onInputChange}
+                      {...settings.colonReplacementFormat}
+                    />
+                  </FormGroup> :
+                  null
+              }
+
               {
                 renameEpisodes &&
                   <div>
diff --git a/src/NzbDrone.Core.Test/OrganizerTests/FileNameBuilderTests/ColonReplacementFixture.cs b/src/NzbDrone.Core.Test/OrganizerTests/FileNameBuilderTests/ColonReplacementFixture.cs
new file mode 100644
index 000000000..6afc72fe2
--- /dev/null
+++ b/src/NzbDrone.Core.Test/OrganizerTests/FileNameBuilderTests/ColonReplacementFixture.cs
@@ -0,0 +1,100 @@
+using System.Collections.Generic;
+using System.Globalization;
+using System.IO;
+using System.Linq;
+using System.Threading;
+using FizzWare.NBuilder;
+using FluentAssertions;
+using Moq;
+using NUnit.Framework;
+using NzbDrone.Core.CustomFormats;
+using NzbDrone.Core.MediaFiles;
+using NzbDrone.Core.MediaFiles.MediaInfo;
+using NzbDrone.Core.Organizer;
+using NzbDrone.Core.Qualities;
+using NzbDrone.Core.Test.Framework;
+using NzbDrone.Core.Tv;
+using NzbDrone.Test.Common;
+
+namespace NzbDrone.Core.Test.OrganizerTests.FileNameBuilderTests
+{
+    [TestFixture]
+    public class ColonReplacementFixture : CoreTest<FileNameBuilder>
+    {
+        private Series _series;
+        private Episode _episode1;
+        private EpisodeFile _episodeFile;
+        private NamingConfig _namingConfig;
+
+        [SetUp]
+        public void Setup()
+        {
+            _series = Builder<Series>
+                    .CreateNew()
+                    .With(s => s.Title = "CSI: Vegas")
+                    .Build();
+
+            _namingConfig = NamingConfig.Default;
+            _namingConfig.RenameEpisodes = true;
+
+            Mocker.GetMock<INamingConfigService>()
+                  .Setup(c => c.GetConfig()).Returns(_namingConfig);
+
+            _episode1 = Builder<Episode>.CreateNew()
+                            .With(e => e.Title = "What Happens in Vegas")
+                            .With(e => e.SeasonNumber = 1)
+                            .With(e => e.EpisodeNumber = 6)
+                            .With(e => e.AbsoluteEpisodeNumber = 100)
+                            .Build();
+
+            _episodeFile = new EpisodeFile { Quality = new QualityModel(Quality.HDTV720p), ReleaseGroup = "SonarrTest" };
+
+            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>());
+        }
+
+        [Test]
+        public void should_replace_colon_followed_by_space_with_space_dash_space_by_default()
+        {
+            _namingConfig.StandardEpisodeFormat = "{Series Title}";
+
+            Subject.BuildFileName(new List<Episode> { _episode1 }, _series, _episodeFile)
+                   .Should().Be("CSI - Vegas");
+        }
+
+        [TestCase("CSI: Vegas", ColonReplacementFormat.Smart, "CSI - Vegas")]
+        [TestCase("CSI: Vegas", ColonReplacementFormat.Dash, "CSI- Vegas")]
+        [TestCase("CSI: Vegas", ColonReplacementFormat.Delete, "CSI Vegas")]
+        [TestCase("CSI: Vegas", ColonReplacementFormat.SpaceDash, "CSI - Vegas")]
+        [TestCase("CSI: Vegas", ColonReplacementFormat.SpaceDashSpace, "CSI - Vegas")]
+        public void should_replace_colon_followed_by_space_with_expected_result(string seriesName, ColonReplacementFormat replacementFormat, string expected)
+        {
+            _series.Title = seriesName;
+            _namingConfig.StandardEpisodeFormat = "{Series Title}";
+            _namingConfig.ColonReplacementFormat = replacementFormat;
+
+            Subject.BuildFileName(new List<Episode> { _episode1 }, _series, _episodeFile)
+                .Should().Be(expected);
+        }
+
+        [TestCase("Series:Title", ColonReplacementFormat.Smart, "Series-Title")]
+        [TestCase("Series:Title", ColonReplacementFormat.Dash, "Series-Title")]
+        [TestCase("Series:Title", ColonReplacementFormat.Delete, "SeriesTitle")]
+        [TestCase("Series:Title", ColonReplacementFormat.SpaceDash, "Series -Title")]
+        [TestCase("Series:Title", ColonReplacementFormat.SpaceDashSpace, "Series - Title")]
+        public void should_replace_colon_with_expected_result(string seriesName, ColonReplacementFormat replacementFormat, string expected)
+        {
+            _series.Title = seriesName;
+            _namingConfig.StandardEpisodeFormat = "{Series Title}";
+            _namingConfig.ColonReplacementFormat = replacementFormat;
+
+            Subject.BuildFileName(new List<Episode> { _episode1 }, _series, _episodeFile)
+                .Should().Be(expected);
+        }
+    }
+}
diff --git a/src/NzbDrone.Core/Datastore/Migration/189_add_colon_replacement_to_naming_config.cs b/src/NzbDrone.Core/Datastore/Migration/189_add_colon_replacement_to_naming_config.cs
new file mode 100644
index 000000000..e669e4f36
--- /dev/null
+++ b/src/NzbDrone.Core/Datastore/Migration/189_add_colon_replacement_to_naming_config.cs
@@ -0,0 +1,14 @@
+using FluentMigrator;
+using NzbDrone.Core.Datastore.Migration.Framework;
+
+namespace NzbDrone.Core.Datastore.Migration
+{
+    [Migration(189)]
+    public class add_colon_replacement_to_naming_config : NzbDroneMigrationBase
+    {
+        protected override void MainDbUpgrade()
+        {
+            Alter.Table("NamingConfig").AddColumn("ColonReplacementFormat").AsInt32().WithDefaultValue(4);
+        }
+    }
+}
diff --git a/src/NzbDrone.Core/Organizer/FileNameBuilder.cs b/src/NzbDrone.Core/Organizer/FileNameBuilder.cs
index 9b4d96a84..364296348 100644
--- a/src/NzbDrone.Core/Organizer/FileNameBuilder.cs
+++ b/src/NzbDrone.Core/Organizer/FileNameBuilder.cs
@@ -377,30 +377,17 @@ namespace NzbDrone.Core.Organizer
             return title;
         }
 
-        public static string CleanFileName(string name, bool replace = true)
+        public static string CleanFileName(string name)
         {
-            string result = name;
-            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);
-            }
-
-            return result.TrimStart(' ', '.').TrimEnd(' ');
+            return CleanFileName(name, NamingConfig.Default);
         }
 
         public static string CleanFolderName(string name)
         {
             name = FileNameCleanupRegex.Replace(name, match => match.Captures[0].Value[0].ToString());
-            return name.Trim(' ', '.');
+            name = name.Trim(' ', '.');
+
+            return CleanFileName(name);
         }
 
         public bool RequiresEpisodeTitle(Series series, List<Episode> episodes)
@@ -867,7 +854,7 @@ namespace NzbDrone.Core.Organizer
                 replacementText = replacementText.Replace(" ", tokenMatch.Separator);
             }
 
-            replacementText = CleanFileName(replacementText, namingConfig.ReplaceIllegalCharacters);
+            replacementText = CleanFileName(replacementText, namingConfig);
 
             if (!replacementText.IsNullOrWhiteSpace())
             {
@@ -1117,6 +1104,53 @@ namespace NzbDrone.Core.Organizer
             // Replace reserved windows device names with an alternative
             return ReservedDeviceNamesRegex.Replace(input, match => match.Value.Replace(".", "_"));
         }
+
+        private static string CleanFileName(string name, NamingConfig namingConfig)
+        {
+            var result = name;
+            string[] badCharacters = { "\\", "/", "<", ">", "?", "*", "|", "\"" };
+            string[] goodCharacters = { "+", "+", "", "", "!", "-", "", "" };
+
+            if (namingConfig.ReplaceIllegalCharacters)
+            {
+                // Smart replaces a colon followed by a space with space dash space for a better appearance
+                if (namingConfig.ColonReplacementFormat == ColonReplacementFormat.Smart)
+                {
+                    result = result.Replace(": ", " - ");
+                    result = result.Replace(":", "-");
+                }
+                else
+                {
+                    var replacement = string.Empty;
+
+                    switch (namingConfig.ColonReplacementFormat)
+                    {
+                        case ColonReplacementFormat.Dash:
+                            replacement = "-";
+                            break;
+                        case ColonReplacementFormat.SpaceDash:
+                            replacement = " -";
+                            break;
+                        case ColonReplacementFormat.SpaceDashSpace:
+                            replacement = " - ";
+                            break;
+                    }
+
+                    result = result.Replace(":", replacement);
+                }
+            }
+            else
+            {
+                result = result.Replace(":", string.Empty);
+            }
+
+            for (var i = 0; i < badCharacters.Length; i++)
+            {
+                result = result.Replace(badCharacters[i], namingConfig.ReplaceIllegalCharacters ? goodCharacters[i] : string.Empty);
+            }
+
+            return result.TrimStart(' ', '.').TrimEnd(' ');
+        }
     }
 
     internal sealed class TokenMatch
@@ -1150,4 +1184,13 @@ namespace NzbDrone.Core.Organizer
         Range = 4,
         PrefixedRange = 5
     }
+
+    public enum ColonReplacementFormat
+    {
+        Delete = 0,
+        Dash = 1,
+        SpaceDash = 2,
+        SpaceDashSpace = 3,
+        Smart = 4
+    }
 }
diff --git a/src/NzbDrone.Core/Organizer/NamingConfig.cs b/src/NzbDrone.Core/Organizer/NamingConfig.cs
index 50f5d254c..57d88d405 100644
--- a/src/NzbDrone.Core/Organizer/NamingConfig.cs
+++ b/src/NzbDrone.Core/Organizer/NamingConfig.cs
@@ -8,6 +8,7 @@ namespace NzbDrone.Core.Organizer
         {
             RenameEpisodes = false,
             ReplaceIllegalCharacters = true,
+            ColonReplacementFormat = ColonReplacementFormat.Smart,
             MultiEpisodeStyle = MultiEpisodeStyle.PrefixedRange,
             StandardEpisodeFormat = "{Series Title} - S{season:00}E{episode:00} - {Episode Title} {Quality Full}",
             DailyEpisodeFormat = "{Series Title} - {Air-Date} - {Episode Title} {Quality Full}",
@@ -19,6 +20,7 @@ namespace NzbDrone.Core.Organizer
 
         public bool RenameEpisodes { get; set; }
         public bool ReplaceIllegalCharacters { get; set; }
+        public ColonReplacementFormat ColonReplacementFormat { get; set; }
         public MultiEpisodeStyle MultiEpisodeStyle { get; set; }
         public string StandardEpisodeFormat { get; set; }
         public string DailyEpisodeFormat { get; set; }
diff --git a/src/Sonarr.Api.V3/Config/NamingConfigResource.cs b/src/Sonarr.Api.V3/Config/NamingConfigResource.cs
index 8b95058a7..4e4116807 100644
--- a/src/Sonarr.Api.V3/Config/NamingConfigResource.cs
+++ b/src/Sonarr.Api.V3/Config/NamingConfigResource.cs
@@ -1,4 +1,4 @@
-using Sonarr.Http.REST;
+using Sonarr.Http.REST;
 
 namespace Sonarr.Api.V3.Config
 {
@@ -6,6 +6,7 @@ namespace Sonarr.Api.V3.Config
     {
         public bool RenameEpisodes { get; set; }
         public bool ReplaceIllegalCharacters { get; set; }
+        public int ColonReplacementFormat { get; set; }
         public int MultiEpisodeStyle { get; set; }
         public string StandardEpisodeFormat { get; set; }
         public string DailyEpisodeFormat { get; set; }
diff --git a/src/Sonarr.Api.V3/Config/NamingExampleResource.cs b/src/Sonarr.Api.V3/Config/NamingExampleResource.cs
index 103609d5d..66e21aff8 100644
--- a/src/Sonarr.Api.V3/Config/NamingExampleResource.cs
+++ b/src/Sonarr.Api.V3/Config/NamingExampleResource.cs
@@ -24,6 +24,7 @@ namespace Sonarr.Api.V3.Config
 
                 RenameEpisodes = model.RenameEpisodes,
                 ReplaceIllegalCharacters = model.ReplaceIllegalCharacters,
+                ColonReplacementFormat = (int)model.ColonReplacementFormat,
                 MultiEpisodeStyle = (int)model.MultiEpisodeStyle,
                 StandardEpisodeFormat = model.StandardEpisodeFormat,
                 DailyEpisodeFormat = model.DailyEpisodeFormat,
@@ -60,6 +61,7 @@ namespace Sonarr.Api.V3.Config
                 RenameEpisodes = resource.RenameEpisodes,
                 ReplaceIllegalCharacters = resource.ReplaceIllegalCharacters,
                 MultiEpisodeStyle = (MultiEpisodeStyle)resource.MultiEpisodeStyle,
+                ColonReplacementFormat = (ColonReplacementFormat)resource.ColonReplacementFormat,
                 StandardEpisodeFormat = resource.StandardEpisodeFormat,
                 DailyEpisodeFormat = resource.DailyEpisodeFormat,
                 AnimeEpisodeFormat = resource.AnimeEpisodeFormat,