diff --git a/.gitignore b/.gitignore
index 55a5659a84..d34dee6a00 100644
--- a/.gitignore
+++ b/.gitignore
@@ -107,6 +107,7 @@
 **/vendor/bundle/ruby/*/gems/rainbow-*/
 **/vendor/bundle/ruby/*/gems/rbi-*/
 **/vendor/bundle/ruby/*/gems/rdoc-*/
+**/vendor/bundle/ruby/*/gems/redcarpet-*/
 **/vendor/bundle/ruby/*/gems/regexp_parser-*/
 **/vendor/bundle/ruby/*/gems/rexml-*/
 **/vendor/bundle/ruby/*/gems/rspec-*/
diff --git a/Library/Homebrew/Gemfile b/Library/Homebrew/Gemfile
index a01e6a7da9..1933a098e4 100644
--- a/Library/Homebrew/Gemfile
+++ b/Library/Homebrew/Gemfile
@@ -16,9 +16,9 @@ end
 # installed gems (should all be require: false)
 # ALL gems that are not vendored should be in a group
 group :doc, optional: true do
+  gem "redcarpet", require: false
   gem "yard", require: false
   gem "yard-sorbet", require: false
-  gem "redcarpet", require: false
 end
 group :ast, optional: true do
   gem "rubocop-ast", require: false
diff --git a/Library/Homebrew/Gemfile.lock b/Library/Homebrew/Gemfile.lock
index 3102788ac6..80af1b6fd3 100644
--- a/Library/Homebrew/Gemfile.lock
+++ b/Library/Homebrew/Gemfile.lock
@@ -53,6 +53,7 @@ GEM
     rbi (0.1.12)
       prism (>= 0.18.0, < 0.28)
       sorbet-runtime (>= 0.5.9204)
+    redcarpet (3.6.0)
     regexp_parser (2.9.0)
     rexml (3.2.6)
     rspec (3.13.0)
@@ -175,6 +176,7 @@ DEPENDENCIES
   patchelf
   plist
   pry
+  redcarpet
   rexml
   rspec
   rspec-github
diff --git a/Library/Homebrew/sorbet/rbi/gems/redcarpet@3.6.0.rbi b/Library/Homebrew/sorbet/rbi/gems/redcarpet@3.6.0.rbi
new file mode 100644
index 0000000000..705a9e6301
--- /dev/null
+++ b/Library/Homebrew/sorbet/rbi/gems/redcarpet@3.6.0.rbi
@@ -0,0 +1,8 @@
+# typed: true
+
+# DO NOT EDIT MANUALLY
+# This is an autogenerated file for types exported from the `redcarpet` gem.
+# Please instead update this file by running `bin/tapioca gem redcarpet`.
+
+# THIS IS AN EMPTY RBI FILE.
+# see https://github.com/Shopify/tapioca#manually-requiring-parts-of-a-gem
diff --git a/Library/Homebrew/vendor/bundle/bundler/setup.rb b/Library/Homebrew/vendor/bundle/bundler/setup.rb
index 633eac9ce0..bff3e2dc2d 100644
--- a/Library/Homebrew/vendor/bundle/bundler/setup.rb
+++ b/Library/Homebrew/vendor/bundle/bundler/setup.rb
@@ -71,6 +71,7 @@ $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/prism-0.27.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/pry-0.14.2/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rbi-0.1.12/lib")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/redcarpet-3.6.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rspec-support-3.13.1/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rspec-core-3.13.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rspec-expectations-3.13.0/lib")