diff --git a/Source/Testably.Abstractions.Testing/Helpers/FileSystemExtensions.cs b/Source/Testably.Abstractions.Testing/Helpers/FileSystemExtensions.cs
index 76d5762e..759c5bf6 100644
--- a/Source/Testably.Abstractions.Testing/Helpers/FileSystemExtensions.cs
+++ b/Source/Testably.Abstractions.Testing/Helpers/FileSystemExtensions.cs
@@ -58,6 +58,11 @@ internal static string GetSubdirectoryPath(this MockFileSystem fileSystem,
 	{
 		if (fileSystem.Execute.Path.IsPathRooted(givenPath))
 		{
+			if (friendlyName is "/." or "/..")
+			{
+				return friendlyName;
+			}
+
 			return fullFilePath;
 		}
 
diff --git a/Source/Testably.Abstractions.Testing/Storage/InMemoryStorage.cs b/Source/Testably.Abstractions.Testing/Storage/InMemoryStorage.cs
index bb668030..69f22067 100644
--- a/Source/Testably.Abstractions.Testing/Storage/InMemoryStorage.cs
+++ b/Source/Testably.Abstractions.Testing/Storage/InMemoryStorage.cs
@@ -204,15 +204,20 @@ public IEnumerable<IStorageLocation> EnumerateLocations(
 				drive = _fileSystem.Storage.MainDrive;
 			}
 
+			string prefix =
+				location.FriendlyName.EndsWith(_fileSystem.Execute.Path.DirectorySeparatorChar)
+					? location.FriendlyName
+					: location.FriendlyName + _fileSystem.Execute.Path.DirectorySeparatorChar;
+
 			yield return InMemoryLocation.New(_fileSystem, drive, fullPath,
-				$"{location.FriendlyName}{_fileSystem.Execute.Path.DirectorySeparatorChar}.");
+				$"{prefix}.");
 			string? parentPath = _fileSystem.Execute.Path.GetDirectoryName(
 				fullPath.TrimEnd(_fileSystem.Execute.Path
 					.DirectorySeparatorChar));
-			if (parentPath != null)
+			if (parentPath != null || !_fileSystem.Execute.IsWindows)
 			{
-				yield return InMemoryLocation.New(_fileSystem, drive, parentPath,
-					$"{location.FriendlyName}{_fileSystem.Execute.Path.DirectorySeparatorChar}..");
+				yield return InMemoryLocation.New(_fileSystem, drive, parentPath ?? "/",
+					$"{prefix}..");
 			}
 		}
 
diff --git a/Tests/Testably.Abstractions.Tests/FileSystem/Directory/EnumerateDirectoriesTests.cs b/Tests/Testably.Abstractions.Tests/FileSystem/Directory/EnumerateDirectoriesTests.cs
index d34cf6e2..fa761a12 100644
--- a/Tests/Testably.Abstractions.Tests/FileSystem/Directory/EnumerateDirectoriesTests.cs
+++ b/Tests/Testably.Abstractions.Tests/FileSystem/Directory/EnumerateDirectoriesTests.cs
@@ -433,6 +433,33 @@ public void
 	}
 #endif
 
+#if FEATURE_FILESYSTEM_ENUMERATION_OPTIONS
+	[SkippableFact]
+	public void
+		EnumerateDirectories_WithEnumerationOptions_ShouldConsiderReturnSpecialDirectoriesCorrectlyForPathRoots()
+	{
+		string root = FileSystem.Path.GetPathRoot(FileSystem.Directory.GetCurrentDirectory())!;
+		EnumerationOptions enumerationOptions = new()
+		{
+			ReturnSpecialDirectories = true
+		};
+
+		List<string> result = FileSystem.Directory
+			.EnumerateDirectories(root, "*", enumerationOptions).ToList();
+
+		if (Test.RunsOnWindows)
+		{
+			result.Should().NotContain(FileSystem.Path.Combine(root, "."));
+			result.Should().NotContain(FileSystem.Path.Combine(root, ".."));
+		}
+		else
+		{
+			result.Should().Contain(FileSystem.Path.Combine(root, "."));
+			result.Should().Contain(FileSystem.Path.Combine(root, ".."));
+		}
+	}
+#endif
+
 	[SkippableTheory]
 	[AutoData]
 	public void EnumerateDirectories_WithNewline_ShouldThrowArgumentException(