diff --git a/src/NzbDrone.Common.Test/DiskTests/DiskTransferServiceFixture.cs b/src/NzbDrone.Common.Test/DiskTests/DiskTransferServiceFixture.cs
index 7995a1dbb..7a9a89bff 100644
--- a/src/NzbDrone.Common.Test/DiskTests/DiskTransferServiceFixture.cs
+++ b/src/NzbDrone.Common.Test/DiskTests/DiskTransferServiceFixture.cs
@@ -403,6 +403,58 @@ namespace NzbDrone.Common.Test.DiskTests
             VerifyCopyFolder(source.FullName, destination.FullName);
         }
 
+        [Test]
+        public void CopyFolder_should_detect_caseinsensitive_parents()
+        {
+            WindowsOnly();
+
+            WithRealDiskProvider();
+
+            var original = GetFilledTempFolder();
+            var root = new DirectoryInfo(GetTempFilePath());
+            var source = new DirectoryInfo(root.FullName + "A/series");
+            var destination = new DirectoryInfo(root.FullName + "a/series");
+
+            Subject.TransferFolder(original.FullName, source.FullName, TransferMode.Copy);
+
+            Assert.Throws<IOException>(() => Subject.TransferFolder(source.FullName, destination.FullName, TransferMode.Copy));
+        }
+
+        [Test]
+        public void CopyFolder_should_detect_caseinsensitive_folder()
+        {
+            WindowsOnly();
+
+            WithRealDiskProvider();
+
+            var original = GetFilledTempFolder();
+            var root = new DirectoryInfo(GetTempFilePath());
+            var source = new DirectoryInfo(root.FullName + "A/series");
+            var destination = new DirectoryInfo(root.FullName + "A/Series");
+
+            Subject.TransferFolder(original.FullName, source.FullName, TransferMode.Copy);
+
+            Assert.Throws<IOException>(() => Subject.TransferFolder(source.FullName, destination.FullName, TransferMode.Copy));
+        }
+
+        [Test]
+        public void CopyFolder_should_not_copy_casesensitive_folder()
+        {
+            MonoOnly();
+
+            WithRealDiskProvider();
+
+            var original = GetFilledTempFolder();
+            var root = new DirectoryInfo(GetTempFilePath());
+            var source = new DirectoryInfo(root.FullName + "A/series");
+            var destination = new DirectoryInfo(root.FullName + "A/Series");
+
+            Subject.TransferFolder(original.FullName, source.FullName, TransferMode.Copy);
+
+            // Note: Although technically possible top copy to different case, we're not allowing it
+            Assert.Throws<IOException>(() => Subject.TransferFolder(source.FullName, destination.FullName, TransferMode.Copy));
+        }
+
         [Test]
         public void CopyFolder_should_ignore_nfs_temp_file()
         {
@@ -452,6 +504,62 @@ namespace NzbDrone.Common.Test.DiskTests
             VerifyMoveFolder(original.FullName, source.FullName, destination.FullName);
         }
 
+        [Test]
+        public void MoveFolder_should_detect_caseinsensitive_parents()
+        {
+            WindowsOnly();
+
+            WithRealDiskProvider();
+
+            var original = GetFilledTempFolder();
+            var root = new DirectoryInfo(GetTempFilePath());
+            var source = new DirectoryInfo(root.FullName + "A/series");
+            var destination = new DirectoryInfo(root.FullName + "a/series");
+
+            Subject.TransferFolder(original.FullName, source.FullName, TransferMode.Copy);
+
+            Assert.Throws<IOException>(() => Subject.TransferFolder(source.FullName, destination.FullName, TransferMode.Move));
+        }
+
+        [Test]
+        public void MoveFolder_should_rename_caseinsensitive_folder()
+        {
+            WindowsOnly();
+
+            WithRealDiskProvider();
+
+            var original = GetFilledTempFolder();
+            var root = new DirectoryInfo(GetTempFilePath());
+            var source = new DirectoryInfo(root.FullName + "A/series");
+            var destination = new DirectoryInfo(root.FullName + "A/Series");
+
+            Subject.TransferFolder(original.FullName, source.FullName, TransferMode.Copy);
+
+            Subject.TransferFolder(source.FullName, destination.FullName, TransferMode.Move);
+
+            source.FullName.GetActualCasing().Should().Be(destination.FullName);
+        }
+
+        [Test]
+        public void MoveFolder_should_rename_casesensitive_folder()
+        {
+            MonoOnly();
+
+            WithRealDiskProvider();
+
+            var original = GetFilledTempFolder();
+            var root = new DirectoryInfo(GetTempFilePath());
+            var source = new DirectoryInfo(root.FullName + "A/series");
+            var destination = new DirectoryInfo(root.FullName + "A/Series");
+
+            Subject.TransferFolder(original.FullName, source.FullName, TransferMode.Copy);
+
+            Subject.TransferFolder(source.FullName, destination.FullName, TransferMode.Move);
+
+            Directory.Exists(source.FullName).Should().Be(false);
+            Directory.Exists(destination.FullName).Should().Be(true);
+        }
+
         [Test]
         public void should_throw_if_destination_is_readonly()
         {
@@ -755,6 +863,10 @@ namespace NzbDrone.Common.Test.DiskTests
                 .Setup(v => v.CreateFolder(It.IsAny<string>()))
                 .Callback<string>(v => fileSystem.Directory.CreateDirectory(v));
 
+            Mocker.GetMock<IDiskProvider>()
+                .Setup(v => v.MoveFolder(It.IsAny<string>(), It.IsAny<string>()))
+                .Callback<string, string>((v, r) => fileSystem.Directory.Move(v, r));
+
             Mocker.GetMock<IDiskProvider>()
                 .Setup(v => v.DeleteFolder(It.IsAny<string>(), It.IsAny<bool>()))
                 .Callback<string, bool>((v, r) => fileSystem.Directory.Delete(v, r));
diff --git a/src/NzbDrone.Common/Disk/DiskTransferService.cs b/src/NzbDrone.Common/Disk/DiskTransferService.cs
index 8a75ed34d..3a274ecfd 100644
--- a/src/NzbDrone.Common/Disk/DiskTransferService.cs
+++ b/src/NzbDrone.Common/Disk/DiskTransferService.cs
@@ -5,7 +5,6 @@ using System.Linq;
 using System.Threading;
 using NLog;
 using NzbDrone.Common.EnsureThat;
-using NzbDrone.Common.EnvironmentInfo;
 using NzbDrone.Common.Extensions;
 
 namespace NzbDrone.Common.Disk
@@ -28,11 +27,53 @@ namespace NzbDrone.Common.Disk
             _logger = logger;
         }
 
+        private string ResolveRealParentPath(string path)
+        {
+            var parentPath = path.GetParentPath();
+            if (!_diskProvider.FolderExists(path))
+            {
+                return path;
+            }
+
+            parentPath = parentPath.GetActualCasing();
+            return parentPath + Path.DirectorySeparatorChar + Path.GetFileName(path);
+        }
+
         public TransferMode TransferFolder(string sourcePath, string targetPath, TransferMode mode)
         {
             Ensure.That(sourcePath, () => sourcePath).IsValidPath();
             Ensure.That(targetPath, () => targetPath).IsValidPath();
 
+            sourcePath = ResolveRealParentPath(sourcePath);
+            targetPath = ResolveRealParentPath(targetPath);
+
+            _logger.Debug("{0} Directory [{1}] > [{2}]", mode, sourcePath, targetPath);
+
+            if (sourcePath == targetPath)
+            {
+                throw new IOException(string.Format("Source and destination can't be the same {0}", sourcePath));
+            }
+
+            if (mode == TransferMode.Move && sourcePath.PathEquals(targetPath, StringComparison.InvariantCultureIgnoreCase) && _diskProvider.FolderExists(targetPath))
+            {
+                // Move folder out of the way to allow case-insensitive renames
+                var tempPath = sourcePath + ".backup~";
+                _logger.Trace("Rename Intermediate Directory [{0}] > [{1}]", sourcePath, tempPath);
+                _diskProvider.MoveFolder(sourcePath, tempPath);
+
+                if (!_diskProvider.FolderExists(targetPath))
+                {
+                    _logger.Trace("Rename Intermediate Directory [{0}] > [{1}]", tempPath, targetPath);
+                    _logger.Debug("Rename Directory [{0}] > [{1}]", sourcePath, targetPath);
+                    _diskProvider.MoveFolder(tempPath, targetPath);
+                    return mode;
+                }
+
+                // There were two separate folders, revert the intermediate rename and let the recursion deal with it
+                _logger.Trace("Rename Intermediate Directory [{0}] > [{1}]", tempPath, sourcePath);
+                _diskProvider.MoveFolder(tempPath, sourcePath);
+            }
+
             if (mode == TransferMode.Move && !_diskProvider.FolderExists(targetPath))
             {
                 var sourceMount = _diskProvider.GetMount(sourcePath);
@@ -41,7 +82,7 @@ namespace NzbDrone.Common.Disk
                 // If we're on the same mount, do a simple folder move.
                 if (sourceMount != null && targetMount != null && sourceMount.RootDirectory == targetMount.RootDirectory)
                 {
-                    _logger.Debug("Move Directory [{0}] > [{1}]", sourcePath, targetPath);
+                    _logger.Debug("Rename Directory [{0}] > [{1}]", sourcePath, targetPath);
                     _diskProvider.MoveFolder(sourcePath, targetPath);
                     return mode;
                 }
@@ -80,6 +121,13 @@ namespace NzbDrone.Common.Disk
 
             if (mode.HasFlag(TransferMode.Move))
             {
+                var totalSize = _diskProvider.GetFileInfos(sourcePath).Sum(v => v.Length);
+
+                if (totalSize > (100 * 1024L * 1024L))
+                {
+                    throw new IOException($"Large files still exist in {sourcePath} after folder move, not deleting source folder");
+                }
+
                 _diskProvider.DeleteFolder(sourcePath, true);
             }
 
@@ -93,7 +141,10 @@ namespace NzbDrone.Common.Disk
             Ensure.That(sourcePath, () => sourcePath).IsValidPath();
             Ensure.That(targetPath, () => targetPath).IsValidPath();
 
-            _logger.Debug("Mirror [{0}] > [{1}]", sourcePath, targetPath);
+            sourcePath = ResolveRealParentPath(sourcePath);
+            targetPath = ResolveRealParentPath(targetPath);
+
+            _logger.Debug("Mirror Folder [{0}] > [{1}]", sourcePath, targetPath);
 
             if (!_diskProvider.FolderExists(targetPath))
             {
@@ -205,6 +256,9 @@ namespace NzbDrone.Common.Disk
             Ensure.That(sourcePath, () => sourcePath).IsValidPath();
             Ensure.That(targetPath, () => targetPath).IsValidPath();
 
+            sourcePath = ResolveRealParentPath(sourcePath);
+            targetPath = ResolveRealParentPath(targetPath);
+
             _logger.Debug("{0} [{1}] > [{2}]", mode, sourcePath, targetPath);
 
             var originalSize = _diskProvider.GetFileSize(sourcePath);