diff --git a/Library/Homebrew/Gemfile.lock b/Library/Homebrew/Gemfile.lock
index 184ab935fa..9915033fe9 100644
--- a/Library/Homebrew/Gemfile.lock
+++ b/Library/Homebrew/Gemfile.lock
@@ -87,7 +87,7 @@ GEM
     patchelf (1.4.0)
       elftools (>= 1.2)
     plist (3.6.0)
-    pry (0.14.1)
+    pry (0.14.2)
       coderay (~> 1.1)
       method_source (~> 1.0)
     public_suffix (5.0.1)
diff --git a/Library/Homebrew/sorbet/rbi/gems/pry@0.14.1.rbi b/Library/Homebrew/sorbet/rbi/gems/pry@0.14.2.rbi
similarity index 99%
rename from Library/Homebrew/sorbet/rbi/gems/pry@0.14.1.rbi
rename to Library/Homebrew/sorbet/rbi/gems/pry@0.14.2.rbi
index 8f04fe9c6f..159b3f812c 100644
--- a/Library/Homebrew/sorbet/rbi/gems/pry@0.14.1.rbi
+++ b/Library/Homebrew/sorbet/rbi/gems/pry@0.14.2.rbi
@@ -4,7 +4,10 @@
 # This is an autogenerated file for types exported from the `pry` gem.
 # Please instead update this file by running `bin/tapioca gem pry`.
 
+::APPLE_GEM_HOME = T.let(T.unsafe(nil), String)
 ::RUBY19 = T.let(T.unsafe(nil), TrueClass)
+::RUBY_FRAMEWORK = T.let(T.unsafe(nil), TrueClass)
+::RUBY_FRAMEWORK_VERSION = T.let(T.unsafe(nil), String)
 
 class BasicObject
   def __binding__; end
@@ -185,6 +188,10 @@ class Pry
     def toplevel_binding; end
     def toplevel_binding=(_arg0); end
     def view_clip(obj, options = T.unsafe(nil)); end
+
+    private
+
+    def mutex_available?; end
   end
 end
 
@@ -1523,7 +1530,6 @@ module Pry::Helpers::Platform
     def linux?; end
     def mac_osx?; end
     def mri?; end
-    def mri_19?; end
     def mri_2?; end
     def windows?; end
     def windows_ansi?; end
@@ -2481,12 +2487,12 @@ class Pry::WrappedModule::Candidate
 
   private
 
-  def class_regexes; end
   def first_line_of_module_definition(file, line); end
   def first_method_source_location; end
   def last_method_source_location; end
   def lines_for_file(*a, &b); end
   def method_candidates(*a, &b); end
+  def module_definition_first_line?(line); end
   def name(*a, &b); end
   def number_of_lines_in_first_chunk; end
   def yard_docs?(*a, &b); end
diff --git a/Library/Homebrew/vendor/bundle/bundler/setup.rb b/Library/Homebrew/vendor/bundle/bundler/setup.rb
index 0bbdbb5cc4..a2d2558802 100644
--- a/Library/Homebrew/vendor/bundle/bundler/setup.rb
+++ b/Library/Homebrew/vendor/bundle/bundler/setup.rb
@@ -82,7 +82,7 @@ $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/parlour-8.1.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/patchelf-1.4.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/plist-3.6.0/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/pry-0.14.1/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-3.0.3/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/unparser-0.6.4/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rbi-0.0.14/lib")