diff --git a/Library/Homebrew/rubocops/cask/shared_filelist_glob.rb b/Library/Homebrew/rubocops/cask/shared_filelist_glob.rb
new file mode 100644
index 0000000000..8f2e4abbac
--- /dev/null
+++ b/Library/Homebrew/rubocops/cask/shared_filelist_glob.rb
@@ -0,0 +1,37 @@
+# typed: true
+# frozen_string_literal: true
+
+module RuboCop
+  module Cop
+    module Cask
+      class SharedFilelistGlob < Base
+        extend AutoCorrector
+
+        def on_send(node)
+          return if node.method_name != :zap
+
+          node.each_descendant(:pair).each do |pair|
+            symbols = pair.children.select(&:sym_type?).map(&:value)
+            next unless symbols.include?(:trash)
+
+            pair.each_descendant(:array).each do |array|
+              regex = /\.sfl\d"$/
+              message = "Use a glob (*) instead of a specific version (ie. sfl2) for trashing Shared File List paths"
+
+              array.children.each do |item|
+                next unless item.source.match?(regex)
+
+                corrected_item = item.source.sub(/sfl\d"$/, "sfl*\"")
+
+                add_offense(item,
+                            message: message) do |corrector|
+                  corrector.replace(item, corrected_item)
+                end
+              end
+            end
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/Library/Homebrew/rubocops/rubocop-cask.rb b/Library/Homebrew/rubocops/rubocop-cask.rb
index 572db73393..44abad52f9 100644
--- a/Library/Homebrew/rubocops/rubocop-cask.rb
+++ b/Library/Homebrew/rubocops/rubocop-cask.rb
@@ -18,6 +18,7 @@ require_relative "cask/discontinued"
 require_relative "cask/homepage_url_trailing_slash"
 require_relative "cask/no_overrides"
 require_relative "cask/on_system_conditionals"
+require_relative "cask/shared_filelist_glob"
 require_relative "cask/stanza_order"
 require_relative "cask/stanza_grouping"
 require_relative "cask/uninstall_methods_order"
diff --git a/Library/Homebrew/test/rubocops/cask/shared_filelist_glob_spec.rb b/Library/Homebrew/test/rubocops/cask/shared_filelist_glob_spec.rb
new file mode 100644
index 0000000000..cc375563d3
--- /dev/null
+++ b/Library/Homebrew/test/rubocops/cask/shared_filelist_glob_spec.rb
@@ -0,0 +1,24 @@
+# frozen_string_literal: true
+
+require "rubocops/rubocop-cask"
+
+describe RuboCop::Cop::Cask::SharedFilelistGlob, :config do
+  it "reports an offense when a zap trash array includes an .sfl2 or .sfl3 file" do
+    expect_offense(<<~CASK)
+      cask "foo" do
+        url "https://example.com/foo.zip"
+
+        zap trash: ["~/Library/Application Support/com.apple.sharedfilelist/com.apple.LSSharedFileList.ApplicationRecentDocuments/org.mozilla.firefox.sfl2"]
+                    ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Use a glob (*) instead of a specific version (ie. sfl2) for trashing Shared File List paths
+      end
+    CASK
+
+    expect_correction(<<~CASK)
+      cask "foo" do
+        url "https://example.com/foo.zip"
+
+        zap trash: ["~/Library/Application Support/com.apple.sharedfilelist/com.apple.LSSharedFileList.ApplicationRecentDocuments/org.mozilla.firefox.sfl*"]
+      end
+    CASK
+  end
+end