diff --git a/src/NzbDrone.Core.Test/OrganizerTests/FileNameBuilderTests/ReservedDeviceNameFixture.cs b/src/NzbDrone.Core.Test/OrganizerTests/FileNameBuilderTests/ReservedDeviceNameFixture.cs
new file mode 100644
index 000000000..eceb0bf2a
--- /dev/null
+++ b/src/NzbDrone.Core.Test/OrganizerTests/FileNameBuilderTests/ReservedDeviceNameFixture.cs
@@ -0,0 +1,97 @@
+using System;
+using System.Collections.Generic;
+using System.Linq;
+using FizzWare.NBuilder;
+using FluentAssertions;
+using NUnit.Framework;
+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 ReservedDeviceNameFixture : CoreTest<FileNameBuilder>
+    {
+        private Artist _artist;
+        private Album _album;
+        private Track _track1;
+        private Medium _medium;
+        private AlbumRelease _release;
+        private TrackFile _trackFile;
+        private NamingConfig _namingConfig;
+
+        [SetUp]
+        public void Setup()
+        {
+            _artist = Builder<Artist>
+                    .CreateNew()
+                    .With(s => s.Name = "Tim Park")
+                    .Build();
+
+            _medium = Builder<Medium>
+                .CreateNew()
+                .With(m => m.Number = 3)
+                .Build();
+
+            _release = Builder<AlbumRelease>
+                .CreateNew()
+                .With(s => s.Media = new List<Medium> { _medium })
+                .With(s => s.Monitored = true)
+                .Build();
+
+            _album = Builder<Album>
+                .CreateNew()
+                .With(s => s.Title = "Hybrid Theory")
+                .With(s => s.AlbumType = "Album")
+                .With(s => s.Disambiguation = "The Best Album")
+                .With(s => s.Genres = new List<string> { "Rock" })
+                .With(s => s.ForeignAlbumId = Guid.NewGuid().ToString())
+                .Build();
+
+            _namingConfig = NamingConfig.Default;
+            _namingConfig.RenameTracks = true;
+
+            Mocker.GetMock<INamingConfigService>()
+                  .Setup(c => c.GetConfig()).Returns(_namingConfig);
+
+            _track1 = Builder<Track>.CreateNew()
+                            .With(e => e.Title = "City Sushi")
+                            .With(e => e.TrackNumber = "6")
+                            .With(e => e.AbsoluteTrackNumber = 6)
+                            .With(e => e.AlbumRelease = _release)
+                            .With(e => e.MediumNumber = _medium.Number)
+                            .With(e => e.ArtistMetadata = _artist.Metadata)
+                            .Build();
+
+            _trackFile = new TrackFile { Quality = new QualityModel(Quality.FLAC), ReleaseGroup = "SonarrTest" };
+
+            Mocker.GetMock<IQualityDefinitionService>()
+                .Setup(v => v.Get(Moq.It.IsAny<Quality>()))
+                .Returns<Quality>(v => Quality.DefaultQualityDefinitions.First(c => c.Quality == v));
+        }
+
+        [TestCase("Con Game", "Con_Game")]
+        [TestCase("Com1 Sat", "Com1_Sat")]
+        public void should_replace_reserved_device_name_in_artist_folder(string title, string expected)
+        {
+            _artist.Name = title;
+            _namingConfig.ArtistFolderFormat = "{Artist.Name}";
+
+            Subject.GetArtistFolder(_artist).Should().Be(expected);
+        }
+
+        [TestCase("Con Game", "Con_Game")]
+        [TestCase("Com1 Sat", "Com1_Sat")]
+        public void should_replace_reserved_device_name_in_file_name(string title, string expected)
+        {
+            _artist.Name = title;
+            _namingConfig.StandardTrackFormat = "{Artist.Name} - {Track Title}";
+
+            Subject.BuildTrackFileName(new List<Track> { _track1 }, _artist, _album, _trackFile).Should().Be($"{expected} - City Sushi");
+        }
+    }
+}
diff --git a/src/NzbDrone.Core/Organizer/FileNameBuilder.cs b/src/NzbDrone.Core/Organizer/FileNameBuilder.cs
index 2f0202674..e2c7e6b2d 100644
--- a/src/NzbDrone.Core/Organizer/FileNameBuilder.cs
+++ b/src/NzbDrone.Core/Organizer/FileNameBuilder.cs
@@ -69,6 +69,8 @@ namespace NzbDrone.Core.Organizer
 
         private static readonly Regex TitlePrefixRegex = new Regex(@"^(The|An|A) (.*?)((?: *\([^)]+\))*)$", RegexOptions.Compiled | RegexOptions.IgnoreCase);
 
+        private static readonly Regex ReservedDeviceNamesRegex = new Regex(@"^(?:aux|com[1-9]|con|lpt[1-9]|nul|prn)\.", RegexOptions.Compiled | RegexOptions.IgnoreCase);
+
         public FileNameBuilder(INamingConfigService namingConfigService,
                                IQualityDefinitionService qualityDefinitionService,
                                ICacheManager cacheManager,
@@ -144,6 +146,7 @@ namespace NzbDrone.Core.Organizer
                 component = FileNameCleanupRegex.Replace(component, match => match.Captures[0].Value[0].ToString());
                 component = TrimSeparatorsRegex.Replace(component, string.Empty);
                 component = component.Replace("{ellipsis}", "...");
+                component = ReplaceReservedDeviceNames(component);
 
                 if (component.IsNotNullOrWhiteSpace())
                 {
@@ -236,6 +239,7 @@ namespace NzbDrone.Core.Organizer
 
                 var component = ReplaceTokens(splitPattern, tokenHandlers, namingConfig);
                 component = CleanFolderName(component);
+                component = ReplaceReservedDeviceNames(component);
 
                 if (component.IsNotNullOrWhiteSpace())
                 {
@@ -644,6 +648,12 @@ namespace NzbDrone.Core.Organizer
             return result.GetByteCount();
         }
 
+        private string ReplaceReservedDeviceNames(string input)
+        {
+            // 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;