diff --git a/Library/Homebrew/cask/artifact/moved.rb b/Library/Homebrew/cask/artifact/moved.rb
index 48861a0f61..ee878de0a5 100644
--- a/Library/Homebrew/cask/artifact/moved.rb
+++ b/Library/Homebrew/cask/artifact/moved.rb
@@ -94,8 +94,10 @@ module Cask
           if target.writable?
             source.children.each { |child| FileUtils.move(child, target + child.basename) }
           else
-            command.run!("/bin/cp", args: ["-pR", "#{source}/*", "#{source}/.*", "#{target}/"],
-                                    sudo: true)
+            source.children.each do |child|
+              command.run!("/bin/cp", args: ["-pR", child, target + child.basename],
+                                      sudo: true)
+            end
           end
           Quarantine.copy_xattrs(source, target)
           source.rmtree
diff --git a/Library/Homebrew/test/cask/artifact/app_spec.rb b/Library/Homebrew/test/cask/artifact/app_spec.rb
index 796f03f19f..da92098599 100644
--- a/Library/Homebrew/test/cask/artifact/app_spec.rb
+++ b/Library/Homebrew/test/cask/artifact/app_spec.rb
@@ -334,5 +334,26 @@ describe Cask::Artifact::App, :cask do
 
       expect(contents_path).to exist
     end
+
+    it "properly handles non-writable directories" do
+      install_phase
+
+      contents_path = target_path.join("Contents")
+
+      allow(target_path).to receive(:writable?).and_return false
+      allow(command).to receive(:run!).and_call_original
+      allow(command).to receive(:run!)
+        .with("/bin/cp", args: ["-pR", source_path.join("Contents"), contents_path],
+                         sudo: true)
+        .and_wrap_original do |original_method, *args, **kwargs|
+          original_method.call(*args, sudo_as_root: false, **kwargs)
+        end
+
+      app.uninstall_phase(command: command, force: force, successor: cask)
+      expect(contents_path).not_to exist
+
+      app.install_phase(command: command, adopt: adopt, force: force, predecessor: cask)
+      expect(contents_path).to exist
+    end
   end
 end