diff --git a/src/File/FileSpec.cs b/src/File/FileSpec.cs
index 924596b..57862ce 100644
--- a/src/File/FileSpec.cs
+++ b/src/File/FileSpec.cs
@@ -1,8 +1,10 @@
 using System;
+using System.Diagnostics;
 using System.Linq;
 
 namespace Devlooped
 {
+    [DebuggerDisplay("{Path}")]
     public class FileSpec
     {
         public static FileSpec WithPath(string path, Uri uri)
diff --git a/src/File/SyncCommand.cs b/src/File/SyncCommand.cs
index e66dadc..a383cbb 100644
--- a/src/File/SyncCommand.cs
+++ b/src/File/SyncCommand.cs
@@ -1,4 +1,5 @@
-using System.IO;
+using System;
+using System.IO;
 using System.Linq;
 using DotNetConfig;
 
@@ -16,12 +17,21 @@ protected override bool OnRemoteUrlMissing(FileSpec spec)
 
             // Clear empty directories
             var dir = new FileInfo(spec.Path).DirectoryName;
-            if (dir != null && !Directory.EnumerateFiles(dir).Any())
-                Directory.Delete(dir);
+            DeleteEmptyDirectories(dir);
 
             Configuration.RemoveSection("file", spec.Path);
 
             return true;
         }
+
+        void DeleteEmptyDirectories(string? dir)
+        {
+            if (dir != null && !Directory.EnumerateFiles(dir).Any() && !Directory.EnumerateDirectories(dir).Any())
+            {
+                var parent = new DirectoryInfo(dir).Parent?.FullName;
+                Directory.Delete(dir);
+                DeleteEmptyDirectories(parent);
+            }
+        }
     }
 }