diff --git a/Library/Homebrew/cleanup.rb b/Library/Homebrew/cleanup.rb
index bbdf2710b38598..eca71f1538e934 100644
--- a/Library/Homebrew/cleanup.rb
+++ b/Library/Homebrew/cleanup.rb
@@ -630,6 +630,20 @@ def prune_prefix_symlinks_and_directories
         end
       end
 
+      require "cask/caskroom"
+      if Cask::Caskroom.path.directory?
+        Cask::Caskroom.path.each_child do |path|
+          path.extend(ObserverPathnameExtension)
+          next if !path.symlink? || path.resolved_path_exists?
+
+          if dry_run?
+            puts "Would remove (broken link): #{path}"
+          else
+            path.unlink
+          end
+        end
+      end
+
       return if dry_run?
 
       return if ObserverPathnameExtension.total.zero?
diff --git a/Library/Homebrew/test/cleanup_spec.rb b/Library/Homebrew/test/cleanup_spec.rb
index b4a09a8721d1c7..acd1fa9a580dbd 100644
--- a/Library/Homebrew/test/cleanup_spec.rb
+++ b/Library/Homebrew/test/cleanup_spec.rb
@@ -95,6 +95,22 @@
     end
   end
 
+  describe "::prune_prefix_symlinks_and_directories" do
+    it "removes broken symlinks for uninstalled migrated Casks" do
+      caskroom = Cask::Caskroom.path
+      old_cask_dir = caskroom/"old"
+      new_cask_dir = caskroom/"new"
+      unrelated_cask_dir = caskroom/"other"
+      unrelated_cask_dir.mkpath
+      FileUtils.ln_s new_cask_dir, old_cask_dir
+
+      cleanup.prune_prefix_symlinks_and_directories
+      expect(unrelated_cask_dir).to exist
+      expect(old_cask_dir).not_to be_a_symlink
+      expect(old_cask_dir).not_to exist
+    end
+  end
+
   specify "::cleanup_formula" do
     f1 = Class.new(Testball) do
       version "1.0"