diff --git a/src/NzbDrone.Common.Test/DiskTests/DiskTransferServiceFixture.cs b/src/NzbDrone.Common.Test/DiskTests/DiskTransferServiceFixture.cs
index 04c5cb40a0..c930f65332 100644
--- a/src/NzbDrone.Common.Test/DiskTests/DiskTransferServiceFixture.cs
+++ b/src/NzbDrone.Common.Test/DiskTests/DiskTransferServiceFixture.cs
@@ -540,6 +540,27 @@ public void MoveFolder_should_rename_caseinsensitive_folder()
             source.FullName.GetActualCasing().Should().Be(destination.FullName);
         }
 
+        [Test]
+        public void TransferFile_should_find_files_with_multiple_slashes_within_their_path()
+        {
+            WithRealDiskProvider();
+
+            var root = GetFilledTempFolder();
+            var rootDir = root.FullName;
+            var fromFileName = "source-file";
+            var from = Path.Combine(rootDir, fromFileName);
+            var to = Path.Combine(rootDir, "destination-file");
+
+            var oneSlash = new string(Path.DirectorySeparatorChar, 1);
+            var threeSlashes = new string(Path.DirectorySeparatorChar, 3);
+            var overSlashed = Path.Combine(rootDir.Replace(oneSlash, threeSlashes), fromFileName);
+
+            File.WriteAllText(from, "Source file");
+
+            var mode = Subject.TransferFile(overSlashed, to, TransferMode.Copy);
+            mode.Should().Be(TransferMode.Copy);
+        }
+
         [Test]
         public void should_throw_if_destination_is_readonly()
         {
diff --git a/src/NzbDrone.Common/Disk/DiskTransferService.cs b/src/NzbDrone.Common/Disk/DiskTransferService.cs
index f89c31b212..2bcf3474b8 100644
--- a/src/NzbDrone.Common/Disk/DiskTransferService.cs
+++ b/src/NzbDrone.Common/Disk/DiskTransferService.cs
@@ -28,15 +28,21 @@ public DiskTransferService(IDiskProvider diskProvider, Logger logger)
 
         private string ResolveRealParentPath(string path)
         {
-            var parentPath = path.GetParentPath();
-            if (!_diskProvider.FolderExists(parentPath))
+            var testExists = path.GetParentPath();
+            if (!_diskProvider.FolderExists(testExists))
             {
                 return path;
             }
 
-            var realParentPath = parentPath.GetActualCasing();
+            var cleanPath = path.GetCleanPath();
+            if (cleanPath != path)
+            {
+                _logger.Warn($"Path '{path}' is not clean, using '{cleanPath}' to resolve the parent path instead");
+            }
 
-            var partialChildPath = path.Substring(parentPath.Length);
+            var parentPath = cleanPath.GetParentPath();
+            var realParentPath = parentPath.GetActualCasing();
+            var partialChildPath = cleanPath.Substring(parentPath.Length);
 
             return realParentPath + partialChildPath;
         }