diff --git a/src/NzbDrone.Common.Test/PathExtensionFixture.cs b/src/NzbDrone.Common.Test/PathExtensionFixture.cs
index 7d9b3497a..c96414d1c 100644
--- a/src/NzbDrone.Common.Test/PathExtensionFixture.cs
+++ b/src/NzbDrone.Common.Test/PathExtensionFixture.cs
@@ -157,6 +157,25 @@ namespace NzbDrone.Common.Test
             path.GetParentPath().Should().Be(parentPath);
         }
 
+        [TestCase(@"C:\Test\mydir", "Test")]
+        [TestCase(@"C:\Test\", @"C:\")]
+        [TestCase(@"C:\", null)]
+        [TestCase(@"\\server\share", null)]
+        [TestCase(@"\\server\share\test", @"\\server\share")]
+        public void path_should_return_parent_name_windows(string path, string parentPath)
+        {
+            WindowsOnly();
+            path.GetParentName().Should().Be(parentPath);
+        }
+
+        [TestCase(@"/", null)]
+        [TestCase(@"/test", "/")]
+        public void path_should_return_parent_name_mono(string path, string parentPath)
+        {
+            PosixOnly();
+            path.GetParentName().Should().Be(parentPath);
+        }
+
         [Test]
         public void path_should_return_parent_for_oversized_path()
         {
diff --git a/src/NzbDrone.Common/Extensions/PathExtensions.cs b/src/NzbDrone.Common/Extensions/PathExtensions.cs
index 32a00f694..bf105d1ec 100644
--- a/src/NzbDrone.Common/Extensions/PathExtensions.cs
+++ b/src/NzbDrone.Common/Extensions/PathExtensions.cs
@@ -86,9 +86,7 @@ namespace NzbDrone.Common.Extensions
 
         public static string GetParentPath(this string childPath)
         {
-            var cleanPath = OsInfo.IsWindows
-                ? PARENT_PATH_END_SLASH_REGEX.Replace(childPath, "")
-                : childPath.TrimEnd(Path.DirectorySeparatorChar);
+            var cleanPath = childPath.GetCleanPath();
 
             if (cleanPath.IsNullOrWhiteSpace())
             {
@@ -98,6 +96,13 @@ namespace NzbDrone.Common.Extensions
             return Directory.GetParent(cleanPath)?.FullName;
         }
 
+        public static string GetParentName(this string childPath)
+        {
+            var cleanPath = childPath.GetCleanPath();
+
+            return Directory.GetParent(cleanPath)?.Name;
+        }
+
         public static string GetCleanPath(this string path)
         {
             var cleanPath = OsInfo.IsWindows
diff --git a/src/NzbDrone.Core.Test/Datastore/Migration/184_remove_invalid_roksbox_metadata_imagesFixture.cs b/src/NzbDrone.Core.Test/Datastore/Migration/184_remove_invalid_roksbox_metadata_imagesFixture.cs
new file mode 100644
index 000000000..a67e6786b
--- /dev/null
+++ b/src/NzbDrone.Core.Test/Datastore/Migration/184_remove_invalid_roksbox_metadata_imagesFixture.cs
@@ -0,0 +1,67 @@
+using System;
+using System.Linq;
+using Dapper;
+using FluentAssertions;
+using NUnit.Framework;
+using NzbDrone.Core.Datastore.Migration;
+using NzbDrone.Core.Test.Framework;
+
+namespace NzbDrone.Core.Test.Datastore.Migration
+{
+    [TestFixture]
+    public class remove_invalid_roksbox_metadata_imagesFixture : MigrationTest<remove_invalid_roksbox_metadata_images>
+    {
+        [Test]
+        public void should_remove_incorrect_roksbox_metadata_images()
+        {
+            var db = WithDapperMigrationTestDb(c =>
+            {
+                c.Insert.IntoTable("MetadataFiles").Row(new
+                {
+                    SeriesId = 1,
+                    Consumer = "RoksboxMetadata",
+                    Type = 5,
+                    RelativePath = @"Season 01\metadata\S01E01.jpg",
+                    LastUpdated = "2023-01-21 00:00:00.000",
+                    SeasonNumber = 1,
+                    EpisodeFileId = 1,
+                    Added = "2023-01-21 00:00:00.000",
+                    Extension = ".jpg"
+                });
+
+                c.Insert.IntoTable("MetadataFiles").Row(new
+                {
+                    SeriesId = 1,
+                    Consumer = "RoksboxMetadata",
+                    Type = 5,
+                    RelativePath = @"Season 01\S01E01.jpg",
+                    LastUpdated = "2023-01-21 00:00:00.000",
+                    SeasonNumber = 1,
+                    EpisodeFileId = 1,
+                    Added = "2023-01-21 00:00:00.000",
+                    Extension = ".jpg"
+                });
+            });
+
+            var metadataFiles = db.Query<MetadataFile184>("SELECT * FROM MetadataFiles");
+
+            metadataFiles.Should().HaveCount(1);
+            metadataFiles.First().RelativePath.Should().NotContain("metadata");
+        }
+    }
+
+    public class MetadataFile184
+    {
+        public int Id { get; set; }
+        public int SeriesId { get; set; }
+        public int? EpisodeFileId { get; set; }
+        public int? SeasonNumber { get; set; }
+        public string RelativePath { get; set; }
+        public DateTime Added { get; set; }
+        public DateTime LastUpdated { get; set; }
+        public string Extension { get; set; }
+        public string Hash { get; set; }
+        public string Consumer { get; set; }
+        public int Type { get; set; }
+    }
+}
diff --git a/src/NzbDrone.Core/Datastore/Migration/184_remove_invalid_roksbox_metadata_images.cs b/src/NzbDrone.Core/Datastore/Migration/184_remove_invalid_roksbox_metadata_images.cs
new file mode 100644
index 000000000..ccb6d1d9e
--- /dev/null
+++ b/src/NzbDrone.Core/Datastore/Migration/184_remove_invalid_roksbox_metadata_images.cs
@@ -0,0 +1,14 @@
+using FluentMigrator;
+using NzbDrone.Core.Datastore.Migration.Framework;
+
+namespace NzbDrone.Core.Datastore.Migration
+{
+    [Migration(184)]
+    public class remove_invalid_roksbox_metadata_images : NzbDroneMigrationBase
+    {
+        protected override void MainDbUpgrade()
+        {
+            Execute.Sql(@"DELETE FROM MetadataFiles WHERE Consumer = 'RoksboxMetadata' AND Type = 5 AND (RelativePath LIKE '%/metadata/%' OR RelativePath LIKE '%\metadata\%')");
+        }
+    }
+}
diff --git a/src/NzbDrone.Core/Extras/Metadata/Consumers/Roksbox/RoksboxMetadata.cs b/src/NzbDrone.Core/Extras/Metadata/Consumers/Roksbox/RoksboxMetadata.cs
index b8e717392..f93243274 100644
--- a/src/NzbDrone.Core/Extras/Metadata/Consumers/Roksbox/RoksboxMetadata.cs
+++ b/src/NzbDrone.Core/Extras/Metadata/Consumers/Roksbox/RoksboxMetadata.cs
@@ -112,7 +112,8 @@ namespace NzbDrone.Core.Extras.Metadata.Consumers.Roksbox
 
                 if (extension == ".jpg")
                 {
-                    if (!Path.GetFileNameWithoutExtension(filename).EndsWith("-thumb"))
+                    if (!Path.GetFileNameWithoutExtension(filename).EndsWith("-thumb") &&
+                        !path.GetParentName().Equals("metadata", StringComparison.InvariantCultureIgnoreCase))
                     {
                         metadata.Type = MetadataType.EpisodeImage;
                         return metadata;