diff --git a/Library/Homebrew/Gemfile b/Library/Homebrew/Gemfile
index 02a9cc0900..a35ac6e2a0 100644
--- a/Library/Homebrew/Gemfile
+++ b/Library/Homebrew/Gemfile
@@ -43,7 +43,6 @@ end
 group :style, optional: true do
   gem "rubocop", require: false
   gem "rubocop-performance", require: false
-  gem "rubocop-rails", require: false
   gem "rubocop-rspec", require: false
   gem "rubocop-sorbet", require: false
 end
@@ -72,7 +71,6 @@ group :audit, :bump_unversioned_casks, :livecheck, optional: true do
 end
 
 # vendored gems (no group)
-gem "activesupport", "<7" # we're actively working to remove this: https://github.com/Homebrew/brew/issues/16190
 gem "addressable"
 gem "patchelf"
 gem "plist"
diff --git a/Library/Homebrew/Gemfile.lock b/Library/Homebrew/Gemfile.lock
index 25f77602da..342dc61a54 100644
--- a/Library/Homebrew/Gemfile.lock
+++ b/Library/Homebrew/Gemfile.lock
@@ -1,12 +1,6 @@
 GEM
   remote: https://rubygems.org/
   specs:
-    activesupport (6.1.7.6)
-      concurrent-ruby (~> 1.0, >= 1.0.2)
-      i18n (>= 1.6, < 2)
-      minitest (>= 5.1)
-      tzinfo (~> 2.0)
-      zeitwerk (~> 2.3)
     addressable (2.8.6)
       public_suffix (>= 2.0.2, < 6.0)
     ast (2.4.2)
@@ -17,7 +11,6 @@ GEM
     coderay (1.1.3)
     commander (4.6.0)
       highline (~> 2.0.0)
-    concurrent-ruby (1.2.3)
     diff-lcs (1.5.0)
     docile (1.4.0)
     elftools (1.2.0)
@@ -26,8 +19,6 @@ GEM
     hana (1.3.7)
     highline (2.0.3)
     hpricot (0.8.6)
-    i18n (1.14.1)
-      concurrent-ruby (~> 1.0)
     json (2.7.1)
     json_schemer (2.1.1)
       hana (~> 1.3)
@@ -60,7 +51,6 @@ GEM
       method_source (~> 1.0)
     public_suffix (5.0.4)
     racc (1.7.3)
-    rack (3.0.8)
     rainbow (3.1.1)
     rbi (0.1.6)
       prism (>= 0.18.0, < 0.20)
@@ -116,11 +106,6 @@ GEM
     rubocop-performance (1.20.2)
       rubocop (>= 1.48.1, < 2.0)
       rubocop-ast (>= 1.30.0, < 2.0)
-    rubocop-rails (2.23.1)
-      activesupport (>= 4.2.0)
-      rack (>= 1.1)
-      rubocop (>= 1.33.0, < 2.0)
-      rubocop-ast (>= 1.30.0, < 2.0)
     rubocop-rspec (2.26.1)
       rubocop (~> 1.40)
       rubocop-capybara (~> 2.17)
@@ -167,8 +152,6 @@ GEM
       thor (>= 1.2.0)
       yard-sorbet
     thor (1.3.0)
-    tzinfo (2.0.6)
-      concurrent-ruby (~> 1.0)
     unf (0.1.4)
       unf_ext
     unf_ext (0.0.9.1)
@@ -178,7 +161,6 @@ GEM
     yard-sorbet (0.8.1)
       sorbet-runtime (>= 0.5)
       yard (>= 0.9)
-    zeitwerk (2.6.12)
 
 PLATFORMS
   aarch64-linux
@@ -188,7 +170,6 @@ PLATFORMS
   x86_64-linux
 
 DEPENDENCIES
-  activesupport (< 7)
   addressable
   bootsnap
   byebug
@@ -210,7 +191,6 @@ DEPENDENCIES
   rubocop
   rubocop-ast
   rubocop-performance
-  rubocop-rails
   rubocop-rspec
   rubocop-sorbet
   ruby-macho
diff --git a/Library/Homebrew/utils/gems.rb b/Library/Homebrew/utils/gems.rb
index 5479d3f419..3ec5cde847 100644
--- a/Library/Homebrew/utils/gems.rb
+++ b/Library/Homebrew/utils/gems.rb
@@ -14,7 +14,7 @@ module Homebrew
 
   # Bump this whenever a committed vendored gem is later added to or exclusion removed from gitignore.
   # This will trigger it to reinstall properly if `brew install-bundler-gems` needs it.
-  VENDOR_VERSION = 5
+  VENDOR_VERSION = 6
   private_constant :VENDOR_VERSION
 
   RUBY_BUNDLE_VENDOR_DIRECTORY = (HOMEBREW_LIBRARY_PATH/"vendor/bundle/ruby").freeze
diff --git a/Library/Homebrew/vendor/bundle/bundler/setup.rb b/Library/Homebrew/vendor/bundle/bundler/setup.rb
index 47bf420ea2..f0c9e4e0df 100644
--- a/Library/Homebrew/vendor/bundle/bundler/setup.rb
+++ b/Library/Homebrew/vendor/bundle/bundler/setup.rb
@@ -27,12 +27,6 @@ else
     end
   end
 end
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/concurrent-ruby-1.2.3/lib/concurrent-ruby")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/i18n-1.14.1/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/minitest-5.21.2/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/tzinfo-2.0.6/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/zeitwerk-2.6.12/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/activesupport-6.1.7.6/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/public_suffix-5.0.4/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/addressable-2.8.6/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/ast-2.4.2/lib")
@@ -63,6 +57,7 @@ $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/json_schemer-2.1.1/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/language_server-protocol-3.17.0.3/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/method_source-1.0.0/lib")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/minitest-5.21.2/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/mustache-1.1.1/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/netrc-0.11.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/parallel-1.24.0/lib")
@@ -79,7 +74,6 @@ $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/x86_64-darwin-15/#{Gem.extension_api_version}/prism-0.19.0")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/prism-0.19.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/pry-0.14.2/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rack-3.0.8/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rbi-0.1.6/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/x86_64-darwin-15/#{Gem.extension_api_version}/rdiscount-2.2.7.3")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rdiscount-2.2.7.3/lib")
@@ -102,7 +96,6 @@ $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rubocop-capybara-2.20.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rubocop-factory_bot-2.25.1/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rubocop-performance-1.20.2/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rubocop-rails-2.23.1/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rubocop-rspec-2.26.1/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rubocop-sorbet-0.7.6/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/ruby-macho-4.0.0/lib")