diff --git a/Library/Homebrew/cask/artifact/abstract_uninstall.rb b/Library/Homebrew/cask/artifact/abstract_uninstall.rb
index a58552f786..32d958f069 100644
--- a/Library/Homebrew/cask/artifact/abstract_uninstall.rb
+++ b/Library/Homebrew/cask/artifact/abstract_uninstall.rb
@@ -385,20 +385,37 @@ module Cask
         [trashed, untrashable]
       end
 
-      def uninstall_rmdir(*directories, command: nil, **_)
-        return if directories.empty?
+      def all_dirs?(*directories)
+        directories.all?(&:directory?)
+      end
+
+      def recursive_rmdir(*directories, command: nil, **_)
+        success = true
+        each_resolved_path(:rmdir, directories) do |_path, resolved_paths|
+          resolved_paths.select(&method(:all_dirs?)).each do |resolved_path|
+            puts resolved_path.sub(Dir.home, "~")
 
-        ohai "Removing directories if empty:"
-        each_resolved_path(:rmdir, directories) do |path, resolved_paths|
-          puts path
-          resolved_paths.select(&:directory?).each do |resolved_path|
             if (ds_store = resolved_path.join(".DS_Store")).exist?
               command.run!("/bin/rm", args: ["-f", "--", ds_store], sudo: true, print_stderr: false)
             end
 
-            command.run("/bin/rmdir", args: ["--", resolved_path], sudo: true, print_stderr: false)
+            unless recursive_rmdir(*resolved_path.children, command: command)
+              success = false
+              next
+            end
+
+            status = command.run("/bin/rmdir", args: ["--", resolved_path], sudo: true, print_stderr: false).success?
+            success &= status
           end
         end
+        success
+      end
+
+      def uninstall_rmdir(*args)
+        return if args.empty?
+
+        ohai "Removing directories if empty:"
+        recursive_rmdir(*args)
       end
     end
   end
diff --git a/Library/Homebrew/test/cask/artifact/uninstall_spec.rb b/Library/Homebrew/test/cask/artifact/uninstall_spec.rb
index 8996884ff7..cd50589dc6 100644
--- a/Library/Homebrew/test/cask/artifact/uninstall_spec.rb
+++ b/Library/Homebrew/test/cask/artifact/uninstall_spec.rb
@@ -14,10 +14,11 @@ describe Cask::Artifact::Uninstall, :cask do
       let(:fake_system_command) { NeverSudoSystemCommand }
       let(:cask) { Cask::CaskLoader.load(cask_path("with-uninstall-rmdir")) }
       let(:empty_directory) { Pathname.new("#{TEST_TMPDIR}/empty_directory_path") }
+      let(:empty_directory_tree) { empty_directory.join("nested", "empty_directory_path") }
       let(:ds_store) { empty_directory.join(".DS_Store") }
 
       before do
-        empty_directory.mkdir
+        empty_directory_tree.mkpath
         FileUtils.touch ds_store
       end
 
@@ -26,7 +27,7 @@ describe Cask::Artifact::Uninstall, :cask do
       end
 
       it "is supported" do
-        expect(empty_directory).to exist
+        expect(empty_directory_tree).to exist
         expect(ds_store).to exist
 
         artifact.post_uninstall_phase(command: fake_system_command)
diff --git a/Library/Homebrew/test/cask/artifact/zap_spec.rb b/Library/Homebrew/test/cask/artifact/zap_spec.rb
index 3c942ef57a..0f1e7da7da 100644
--- a/Library/Homebrew/test/cask/artifact/zap_spec.rb
+++ b/Library/Homebrew/test/cask/artifact/zap_spec.rb
@@ -12,10 +12,11 @@ describe Cask::Artifact::Zap, :cask do
       let(:fake_system_command) { NeverSudoSystemCommand }
       let(:cask) { Cask::CaskLoader.load(cask_path("with-zap-rmdir")) }
       let(:empty_directory) { Pathname.new("#{TEST_TMPDIR}/empty_directory_path") }
+      let(:empty_directory_tree) { empty_directory.join("nested", "empty_directory_path") }
       let(:ds_store) { empty_directory.join(".DS_Store") }
 
       before do
-        empty_directory.mkdir
+        empty_directory_tree.mkpath
         FileUtils.touch ds_store
       end
 
@@ -24,7 +25,7 @@ describe Cask::Artifact::Zap, :cask do
       end
 
       it "is supported" do
-        expect(empty_directory).to exist
+        expect(empty_directory_tree).to exist
         expect(ds_store).to exist
 
         artifact.zap_phase(command: fake_system_command)