diff --git a/src/NzbDrone.Core.Test/RootFolderTests/GetBestRootFolderPathFixture.cs b/src/NzbDrone.Core.Test/RootFolderTests/GetBestRootFolderPathFixture.cs
new file mode 100644
index 000000000..49a013703
--- /dev/null
+++ b/src/NzbDrone.Core.Test/RootFolderTests/GetBestRootFolderPathFixture.cs
@@ -0,0 +1,48 @@
+using System.Linq;
+using FluentAssertions;
+using Moq;
+using NUnit.Framework;
+using NzbDrone.Common.Disk;
+using NzbDrone.Core.RootFolders;
+using NzbDrone.Core.Test.Framework;
+using NzbDrone.Test.Common;
+
+namespace NzbDrone.Core.Test.RootFolderTests
+{
+    [TestFixture]
+    public class GetBestRootFolderPathFixture : CoreTest<RootFolderService>
+    {
+        private void GivenRootFolders(params string[] paths)
+        {
+            Mocker.GetMock<IRootFolderRepository>()
+                .Setup(s => s.All())
+                .Returns(paths.Select(p => new RootFolder { Path = p }));
+        }
+
+        [Test]
+        public void should_return_root_folder_that_is_parent_path()
+        {
+            GivenRootFolders(@"C:\Test\Music".AsOsAgnostic(), @"D:\Test\Music".AsOsAgnostic());
+            Subject.GetBestRootFolderPath(@"C:\Test\Music\Series Title".AsOsAgnostic()).Should().Be(@"C:\Test\Music".AsOsAgnostic());
+        }
+
+        [Test]
+        public void should_return_root_folder_that_is_grandparent_path()
+        {
+            GivenRootFolders(@"C:\Test\Music".AsOsAgnostic(), @"D:\Test\Music".AsOsAgnostic());
+            Subject.GetBestRootFolderPath(@"C:\Test\Music\S\Series Title".AsOsAgnostic()).Should().Be(@"C:\Test\Music".AsOsAgnostic());
+        }
+
+        [Test]
+        public void should_get_parent_path_from_diskProvider_if_matching_root_folder_is_not_found()
+        {
+            var seriesPath = @"T:\Test\Music\Series Title".AsOsAgnostic();
+
+            GivenRootFolders(@"C:\Test\Music".AsOsAgnostic(), @"D:\Test\Music".AsOsAgnostic());
+            Subject.GetBestRootFolderPath(seriesPath);
+
+            Mocker.GetMock<IDiskProvider>()
+                .Verify(v => v.GetParentFolder(seriesPath), Times.Once);
+        }
+    }
+}
diff --git a/src/NzbDrone.Core/HealthCheck/Checks/RootFolderCheck.cs b/src/NzbDrone.Core/HealthCheck/Checks/RootFolderCheck.cs
index ecdaf5e24..501630ae1 100644
--- a/src/NzbDrone.Core/HealthCheck/Checks/RootFolderCheck.cs
+++ b/src/NzbDrone.Core/HealthCheck/Checks/RootFolderCheck.cs
@@ -4,6 +4,7 @@ using NzbDrone.Core.ImportLists;
 using NzbDrone.Core.MediaFiles.Events;
 using NzbDrone.Core.Music;
 using NzbDrone.Core.Music.Events;
+using NzbDrone.Core.RootFolders;
 
 namespace NzbDrone.Core.HealthCheck.Checks
 {
@@ -16,21 +17,24 @@ namespace NzbDrone.Core.HealthCheck.Checks
         private readonly IArtistService _artistService;
         private readonly IImportListFactory _importListFactory;
         private readonly IDiskProvider _diskProvider;
+        private readonly IRootFolderService _rootFolderService;
 
-        public RootFolderCheck(IArtistService artistService, IImportListFactory importListFactory, IDiskProvider diskProvider)
+        public RootFolderCheck(IArtistService artistService, IImportListFactory importListFactory, IDiskProvider diskProvider, IRootFolderService rootFolderService)
         {
             _artistService = artistService;
             _importListFactory = importListFactory;
             _diskProvider = diskProvider;
+            _rootFolderService = rootFolderService;
         }
 
         public override HealthCheck Check()
         {
-            var missingRootFolders = _artistService.GetAllArtists()
-                                                   .Select(s => _diskProvider.GetParentFolder(s.Path))
-                                                   .Distinct()
-                                                   .Where(s => !_diskProvider.FolderExists(s))
-                                                   .ToList();
+            var rootFolders = _artistService.GetAllArtists()
+                                                           .Select(s => _rootFolderService.GetBestRootFolderPath(s.Path))
+                                                           .Distinct();
+
+            var missingRootFolders = rootFolders.Where(s => !_diskProvider.FolderExists(s))
+                                                          .ToList();
 
             missingRootFolders.AddRange(_importListFactory.All()
                 .Select(s => s.RootFolderPath)
diff --git a/src/NzbDrone.Core/RootFolders/RootFolderService.cs b/src/NzbDrone.Core/RootFolders/RootFolderService.cs
index 368d668b9..cb85af184 100644
--- a/src/NzbDrone.Core/RootFolders/RootFolderService.cs
+++ b/src/NzbDrone.Core/RootFolders/RootFolderService.cs
@@ -153,7 +153,7 @@ namespace NzbDrone.Core.RootFolders
 
             if (possibleRootFolder == null)
             {
-                return Path.GetDirectoryName(path);
+                return _diskProvider.GetParentFolder(path);
             }
 
             return possibleRootFolder.Path;