diff --git a/Library/Homebrew/cask/artifact/moved.rb b/Library/Homebrew/cask/artifact/moved.rb
index e7d8d24847cee..67b0ca2e5a014 100644
--- a/Library/Homebrew/cask/artifact/moved.rb
+++ b/Library/Homebrew/cask/artifact/moved.rb
@@ -40,13 +40,13 @@ def move(force: false, command: nil, **options)
         end
 
         ohai "Moving #{self.class.english_name} '#{source.basename}' to '#{target}'."
-        if target.dirname.parent.writable?
+        if target.dirname.ascend.find(&:directory?).writable?
           target.dirname.mkpath
         else
           command.run!("/bin/mkdir", args: ["-p", target.dirname], sudo: true)
         end
 
-        if target.parent.writable?
+        if target.dirname.writable?
           FileUtils.move(source, target)
         else
           command.run!("/bin/mv", args: [source, target], sudo: true)