diff --git a/src/NzbDrone.Core.Test/OrganizerTests/FileNameBuilderTests/NestedFileNameBuilderFixture.cs b/src/NzbDrone.Core.Test/OrganizerTests/FileNameBuilderTests/NestedFileNameBuilderFixture.cs
new file mode 100644
index 000000000..16da0dea0
--- /dev/null
+++ b/src/NzbDrone.Core.Test/OrganizerTests/FileNameBuilderTests/NestedFileNameBuilderFixture.cs
@@ -0,0 +1,127 @@
+using System;
+using System.Collections.Generic;
+using System.Linq;
+using FizzWare.NBuilder;
+using FluentAssertions;
+using NUnit.Framework;
+using NzbDrone.Core.Books;
+using NzbDrone.Core.MediaFiles;
+using NzbDrone.Core.Organizer;
+using NzbDrone.Core.Qualities;
+using NzbDrone.Core.Test.Framework;
+using NzbDrone.Test.Common;
+
+namespace NzbDrone.Core.Test.OrganizerTests.FileNameBuilderTests
+{
+    [TestFixture]
+    public class NestedFileNameBuilderFixture : CoreTest<FileNameBuilder>
+    {
+        private Author _artist;
+        private Book _album;
+        private Edition _release;
+        private BookFile _trackFile;
+        private NamingConfig _namingConfig;
+
+        [SetUp]
+        public void Setup()
+        {
+            _artist = Builder<Author>
+                    .CreateNew()
+                    .With(s => s.Name = "AuthorName")
+                    .With(s => s.Metadata = new AuthorMetadata
+                    {
+                        Disambiguation = "US Author",
+                        Name = "AuthorName"
+                    })
+                    .Build();
+
+            _album = Builder<Book>
+                .CreateNew()
+                .With(s => s.Author = _artist)
+                .With(s => s.AuthorMetadata = _artist.Metadata.Value)
+                .With(s => s.Title = "A Novel")
+                .With(s => s.ReleaseDate = new DateTime(2020, 1, 15))
+                .With(s => s.SeriesLinks = new List<SeriesBookLink>())
+                .Build();
+
+            _release = Builder<Edition>
+                .CreateNew()
+                .With(s => s.Monitored = true)
+                .With(s => s.Book = _album)
+                .With(s => s.Title = "A Novel")
+                .With(s => s.ReleaseDate = new DateTime(2020, 1, 15))
+                .Build();
+
+            _namingConfig = NamingConfig.Default;
+            _namingConfig.RenameBooks = true;
+
+            Mocker.GetMock<INamingConfigService>()
+                  .Setup(c => c.GetConfig()).Returns(_namingConfig);
+
+            _trackFile = Builder<BookFile>.CreateNew()
+                .With(e => e.Quality = new QualityModel(Quality.MOBI))
+                .With(e => e.ReleaseGroup = "ReadarrTest")
+                .Build();
+
+            Mocker.GetMock<IQualityDefinitionService>()
+                .Setup(v => v.Get(Moq.It.IsAny<Quality>()))
+                .Returns<Quality>(v => Quality.DefaultQualityDefinitions.First(c => c.Quality == v));
+        }
+
+        private void WithSeries()
+        {
+            _album.SeriesLinks = new List<SeriesBookLink>
+            {
+                new SeriesBookLink
+                {
+                    Series = new Series
+                    {
+                        Title = "A Series",
+                    },
+                    Position = "2-3",
+                    SeriesPosition = 1
+                }
+            };
+        }
+
+        [Test]
+        public void should_build_nested_standard_track_filename_with_forward_slash()
+        {
+            WithSeries();
+
+            _namingConfig.StandardBookFormat = "{Book Series}/{Book SeriesTitle - }{Book Title} {(Release Year)}";
+
+            var name = Subject.BuildBookFileName(_artist, _release, _trackFile)
+                .Should().Be("A Series\\A Series #2-3 - A Novel (2020)".AsOsAgnostic());
+        }
+
+        [Test]
+        public void should_build_standard_track_filename_with_forward_slash()
+        {
+            _namingConfig.StandardBookFormat = "{Book Series}/{Book SeriesTitle - }{Book Title} {(Release Year)}";
+
+            Subject.BuildBookFileName(_artist, _release, _trackFile)
+                .Should().Be("A Novel (2020)".AsOsAgnostic());
+        }
+
+        [Test]
+        public void should_build_nested_standard_track_filename_with_back_slash()
+        {
+            WithSeries();
+
+            _namingConfig.StandardBookFormat = "{Book Series}\\{Book SeriesTitle - }{Book Title} {(Release Year)}";
+
+            Subject.BuildBookFileName(_artist, _release, _trackFile)
+                   .Should().Be("A Series\\A Series #2-3 - A Novel (2020)".AsOsAgnostic());
+        }
+
+        [Test]
+        public void should_build_standard_track_filename_with_back_slash()
+        {
+            _namingConfig.StandardBookFormat = "{Book Series}\\{Book SeriesTitle - }{Book Title} {(Release Year)}";
+
+            Subject.BuildBookFileName(_artist, _release, _trackFile)
+                .Should().Be("A Novel (2020)".AsOsAgnostic());
+        }
+    }
+}
diff --git a/src/NzbDrone.Core/Organizer/FileNameBuilder.cs b/src/NzbDrone.Core/Organizer/FileNameBuilder.cs
index 1d59b0e74..51bf9be49 100644
--- a/src/NzbDrone.Core/Organizer/FileNameBuilder.cs
+++ b/src/NzbDrone.Core/Organizer/FileNameBuilder.cs
@@ -88,9 +88,6 @@ namespace NzbDrone.Core.Organizer
 
             var pattern = namingConfig.StandardBookFormat;
 
-            var subFolders = pattern.Split(new[] { '/', '\\' }, StringSplitOptions.RemoveEmptyEntries);
-            var safePattern = subFolders.Aggregate("", (current, folderLevel) => Path.Combine(current, folderLevel));
-
             var tokenHandlers = new Dictionary<string, Func<TokenMatch, string>>(FileNameBuilderTokenEqualityComparer.Instance);
 
             AddAuthorTokens(tokenHandlers, author);
@@ -100,13 +97,26 @@ namespace NzbDrone.Core.Organizer
             AddMediaInfoTokens(tokenHandlers, bookFile);
             AddPreferredWords(tokenHandlers, author, bookFile, preferredWords);
 
-            var fileName = ReplacePartTokens(safePattern, tokenHandlers, namingConfig);
-            fileName = ReplaceTokens(fileName, tokenHandlers, namingConfig).Trim();
+            var splitPatterns = pattern.Split(new char[] { '\\', '/' }, StringSplitOptions.RemoveEmptyEntries);
+            var components = new List<string>();
+
+            foreach (var s in splitPatterns)
+            {
+                var splitPattern = s;
+
+                var component = ReplacePartTokens(splitPattern, tokenHandlers, namingConfig).Trim();
+                component = ReplaceTokens(component, tokenHandlers, namingConfig).Trim();
 
-            fileName = FileNameCleanupRegex.Replace(fileName, match => match.Captures[0].Value[0].ToString());
-            fileName = TrimSeparatorsRegex.Replace(fileName, string.Empty);
+                component = FileNameCleanupRegex.Replace(component, match => match.Captures[0].Value[0].ToString());
+                component = TrimSeparatorsRegex.Replace(component, string.Empty);
+
+                if (component.IsNotNullOrWhiteSpace())
+                {
+                    components.Add(component);
+                }
+            }
 
-            return fileName;
+            return Path.Combine(components.ToArray());
         }
 
         public string BuildBookFilePath(Author author, Edition edition, string fileName, string extension)
@@ -175,11 +185,28 @@ namespace NzbDrone.Core.Organizer
                 namingConfig = _namingConfigService.GetConfig();
             }
 
+            var pattern = namingConfig.AuthorFolderFormat;
             var tokenHandlers = new Dictionary<string, Func<TokenMatch, string>>(FileNameBuilderTokenEqualityComparer.Instance);
 
             AddAuthorTokens(tokenHandlers, author);
 
-            return CleanFolderName(ReplaceTokens(namingConfig.AuthorFolderFormat, tokenHandlers, namingConfig));
+            var splitPatterns = pattern.Split(new char[] { '\\', '/' }, StringSplitOptions.RemoveEmptyEntries);
+            var components = new List<string>();
+
+            foreach (var s in splitPatterns)
+            {
+                var splitPattern = s;
+
+                var component = ReplaceTokens(splitPattern, tokenHandlers, namingConfig);
+                component = CleanFolderName(component);
+
+                if (component.IsNotNullOrWhiteSpace())
+                {
+                    components.Add(component);
+                }
+            }
+
+            return Path.Combine(components.ToArray());
         }
 
         public static string CleanTitle(string title)