diff --git a/Library/Homebrew/Gemfile.lock b/Library/Homebrew/Gemfile.lock
index fd3156a293..a688c44723 100644
--- a/Library/Homebrew/Gemfile.lock
+++ b/Library/Homebrew/Gemfile.lock
@@ -18,7 +18,7 @@ GEM
     commander (4.6.0)
       highline (~> 2.0.0)
     concurrent-ruby (1.2.2)
-    connection_pool (2.3.0)
+    connection_pool (2.4.0)
     did_you_mean (1.6.3)
     diff-lcs (1.5.0)
     docile (1.4.0)
diff --git a/Library/Homebrew/sorbet/rbi/gems/connection_pool@2.3.0.rbi b/Library/Homebrew/sorbet/rbi/gems/connection_pool@2.4.0.rbi
similarity index 92%
rename from Library/Homebrew/sorbet/rbi/gems/connection_pool@2.3.0.rbi
rename to Library/Homebrew/sorbet/rbi/gems/connection_pool@2.4.0.rbi
index 05e842256d..ec752547a7 100644
--- a/Library/Homebrew/sorbet/rbi/gems/connection_pool@2.3.0.rbi
+++ b/Library/Homebrew/sorbet/rbi/gems/connection_pool@2.4.0.rbi
@@ -8,7 +8,7 @@ class ConnectionPool
   def initialize(options = T.unsafe(nil), &block); end
 
   def available; end
-  def checkin; end
+  def checkin(force: T.unsafe(nil)); end
   def checkout(options = T.unsafe(nil)); end
   def reload(&block); end
   def shutdown(&block); end
@@ -17,12 +17,14 @@ class ConnectionPool
   def with(options = T.unsafe(nil)); end
 
   class << self
+    def after_fork; end
     def wrap(options, &block); end
   end
 end
 
 ConnectionPool::DEFAULTS = T.let(T.unsafe(nil), Hash)
 class ConnectionPool::Error < ::RuntimeError; end
+ConnectionPool::INSTANCES = T.let(T.unsafe(nil), ObjectSpace::WeakMap[T.untyped])
 class ConnectionPool::PoolShuttingDownError < ::ConnectionPool::Error; end
 
 class ConnectionPool::TimedStack
diff --git a/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi b/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi
index 9f9e78ea77..cac311ebe9 100644
--- a/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi
+++ b/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi
@@ -5184,6 +5184,7 @@ class Object
   HOMEBREW_BREW_FILE = ::T.let(nil, ::T.untyped)
   HOMEBREW_CACHE = ::T.let(nil, ::T.untyped)
   HOMEBREW_CACHE_FORMULA = ::T.let(nil, ::T.untyped)
+  HOMEBREW_CASK_APPDIR_PLACEHOLDER = ::T.let(nil, ::T.untyped)
   HOMEBREW_CASK_TAP_CASK_REGEX = ::T.let(nil, ::T.untyped)
   HOMEBREW_CELLAR = ::T.let(nil, ::T.untyped)
   HOMEBREW_CORE_DEFAULT_GIT_REMOTE = ::T.let(nil, ::T.untyped)
@@ -5195,6 +5196,7 @@ class Object
   HOMEBREW_DEFAULT_TEMP = ::T.let(nil, ::T.untyped)
   HOMEBREW_DOCS_WWW = ::T.let(nil, ::T.untyped)
   HOMEBREW_GITHUB_PACKAGES_AUTH = ::T.let(nil, ::T.untyped)
+  HOMEBREW_HOME_PLACEHOLDER = ::T.let(nil, ::T.untyped)
   HOMEBREW_LIBRARY = ::T.let(nil, ::T.untyped)
   HOMEBREW_LIBRARY_PATH = ::T.let(nil, ::T.untyped)
   HOMEBREW_LINKED_KEGS = ::T.let(nil, ::T.untyped)
diff --git a/Library/Homebrew/vendor/bundle/bundler/setup.rb b/Library/Homebrew/vendor/bundle/bundler/setup.rb
index dab3881c96..47afc9e3b2 100644
--- a/Library/Homebrew/vendor/bundle/bundler/setup.rb
+++ b/Library/Homebrew/vendor/bundle/bundler/setup.rb
@@ -42,7 +42,7 @@ $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/coderay-1.1.3/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/highline-2.0.3/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/commander-4.6.0/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/connection_pool-2.3.0/lib")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/connection_pool-2.4.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/did_you_mean-1.6.3/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/diff-lcs-1.5.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/docile-1.4.0/lib")