diff --git a/src/Tgstation.Server.Host/IO/DefaultIOManager.cs b/src/Tgstation.Server.Host/IO/DefaultIOManager.cs
index c303d0a008..58b0348172 100644
--- a/src/Tgstation.Server.Host/IO/DefaultIOManager.cs
+++ b/src/Tgstation.Server.Host/IO/DefaultIOManager.cs
@@ -30,15 +30,17 @@ namespace Tgstation.Server.Host.IO
 		{
 			var tasks = new List<Task>();
 
+			// check if we are a symbolic link
+			if (!dir.Attributes.HasFlag(FileAttributes.Directory) || dir.Attributes.HasFlag(FileAttributes.ReparsePoint))
+			{
+				dir.Delete();
+				return;
+			}
+
 			foreach (var subDir in dir.EnumerateDirectories())
 			{
 				cancellationToken.ThrowIfCancellationRequested();
-
-				// if below succeeds this is probably a symlink
-				if (!subDir.Attributes.HasFlag(FileAttributes.Directory) || subDir.Attributes.HasFlag(FileAttributes.ReparsePoint))
-					subDir.Delete();
-				else
-					tasks.Add(NormalizeAndDelete(subDir, cancellationToken));
+				tasks.Add(NormalizeAndDelete(subDir, cancellationToken));
 			}
 
 			foreach (var file in dir.EnumerateFiles())
diff --git a/src/Tgstation.Server.Host/IO/IIOManager.cs b/src/Tgstation.Server.Host/IO/IIOManager.cs
index 4ce21a7c97..ec56b0209a 100644
--- a/src/Tgstation.Server.Host/IO/IIOManager.cs
+++ b/src/Tgstation.Server.Host/IO/IIOManager.cs
@@ -139,7 +139,7 @@ namespace Tgstation.Server.Host.IO
 		Task CreateDirectory(string path, CancellationToken cancellationToken);
 
 		/// <summary>
-		/// Recursively delete a directory
+		/// Recursively delete a directory, removes and does not enter any symlinks encounterd.
 		/// </summary>
 		/// <param name="path">The path to the directory to delete</param>
 		/// <param name="cancellationToken">A <see cref="CancellationToken"/> for the operation</param>