diff --git a/.gitignore b/.gitignore
index 96ec003b86cb2..df5ca018c167e 100644
--- a/.gitignore
+++ b/.gitignore
@@ -23,6 +23,15 @@
 **/.bundle/cache
 **/vendor/bundle
 **/vendor/ruby
+**/vendor/bundle-standalone/ruby/*/cache
+**/vendor/bundle-standalone/ruby/*/gems/*/*
+**/vendor/bundle-standalone/ruby/*/specifications
+
+# Unignore vendored gems
+!**/vendor/bundle-standalone/ruby/*/gems/*/lib
+
+# Ignore backports gem (we don't need all files)
+**/vendor/bundle-standalone/ruby/*/gems/backports-*/lib
 
 # Ignore `bin` contents (again).
 /bin
diff --git a/Library/Homebrew/cask/artifact/pkg.rb b/Library/Homebrew/cask/artifact/pkg.rb
index 45e3bba1287f9..bade72ab9fa18 100644
--- a/Library/Homebrew/cask/artifact/pkg.rb
+++ b/Library/Homebrew/cask/artifact/pkg.rb
@@ -1,4 +1,4 @@
-require "vendor/plist/plist"
+require "plist"
 
 require "cask/artifact/abstract_artifact"
 
diff --git a/Library/Homebrew/extend/string.rb b/Library/Homebrew/extend/string.rb
index c94bfc83459be..54c16633076a5 100644
--- a/Library/Homebrew/extend/string.rb
+++ b/Library/Homebrew/extend/string.rb
@@ -1,5 +1,5 @@
 # Contains backports from newer versions of Ruby
-require_relative "../vendor/backports/string"
+require "backports/2.4.0/string/match"
 
 class String
   # String.chomp, but if result is empty: returns nil instead.
diff --git a/Library/Homebrew/load_path.rb b/Library/Homebrew/load_path.rb
index bab8941a97ab2..678263d3224e7 100644
--- a/Library/Homebrew/load_path.rb
+++ b/Library/Homebrew/load_path.rb
@@ -5,3 +5,5 @@
 unless $LOAD_PATH.include?(HOMEBREW_LIBRARY_PATH.to_s)
   $LOAD_PATH.push(HOMEBREW_LIBRARY_PATH.to_s)
 end
+
+require "vendor/bundle-standalone/bundler/setup"
diff --git a/Library/Homebrew/os/mac/mach.rb b/Library/Homebrew/os/mac/mach.rb
index 7ec65439db5ba..0ab7a0d3a7caa 100644
--- a/Library/Homebrew/os/mac/mach.rb
+++ b/Library/Homebrew/os/mac/mach.rb
@@ -1,4 +1,4 @@
-require "vendor/macho/macho"
+require "macho"
 require "os/mac/architecture_list"
 
 module MachOShim
diff --git a/Library/Homebrew/system_command.rb b/Library/Homebrew/system_command.rb
index 571b3540be847..c1614cc95d70e 100644
--- a/Library/Homebrew/system_command.rb
+++ b/Library/Homebrew/system_command.rb
@@ -1,6 +1,6 @@
 require "open3"
 require "ostruct"
-require "vendor/plist/plist"
+require "plist"
 require "shellwords"
 
 require "extend/io"
diff --git a/Library/Homebrew/vendor/.bundle/config b/Library/Homebrew/vendor/.bundle/config
new file mode 100644
index 0000000000000..9b31762860330
--- /dev/null
+++ b/Library/Homebrew/vendor/.bundle/config
@@ -0,0 +1,4 @@
+---
+BUNDLE_PATH: "bundle-standalone"
+BUNDLE_DISABLE_SHARED_GEMS: "true"
+BUNDLE_BIN: "false"
diff --git a/Library/Homebrew/vendor/Gemfile b/Library/Homebrew/vendor/Gemfile
new file mode 100644
index 0000000000000..70cbcaa2263ed
--- /dev/null
+++ b/Library/Homebrew/vendor/Gemfile
@@ -0,0 +1,5 @@
+source "https://rubygems.org"
+
+gem "backports"
+gem "plist"
+gem "ruby-macho"
diff --git a/Library/Homebrew/vendor/Gemfile.lock b/Library/Homebrew/vendor/Gemfile.lock
new file mode 100644
index 0000000000000..e03f3113bf6d7
--- /dev/null
+++ b/Library/Homebrew/vendor/Gemfile.lock
@@ -0,0 +1,17 @@
+GEM
+  remote: https://rubygems.org/
+  specs:
+    backports (3.8.0)
+    plist (3.3.0)
+    ruby-macho (2.0.0)
+
+PLATFORMS
+  ruby
+
+DEPENDENCIES
+  backports
+  plist
+  ruby-macho
+
+BUNDLED WITH
+   1.16.4
diff --git a/Library/Homebrew/vendor/bundle-standalone/bundler/setup.rb b/Library/Homebrew/vendor/bundle-standalone/bundler/setup.rb
new file mode 100644
index 0000000000000..34e086a93ca57
--- /dev/null
+++ b/Library/Homebrew/vendor/bundle-standalone/bundler/setup.rb
@@ -0,0 +1,9 @@
+require 'rbconfig'
+# ruby 1.8.7 doesn't define RUBY_ENGINE
+ruby_engine = defined?(RUBY_ENGINE) ? RUBY_ENGINE : 'ruby'
+ruby_version = RbConfig::CONFIG["ruby_version"]
+path = File.expand_path('..', __FILE__)
+$:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/backports-3.8.0/lib"
+$:.unshift "#{path}/"
+$:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/plist-3.3.0/lib"
+$:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/ruby-macho-2.0.0/lib"
diff --git a/Library/Homebrew/vendor/backports/string.rb b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/backports-3.8.0/lib/backports/2.4.0/string/match.rb
similarity index 66%
rename from Library/Homebrew/vendor/backports/string.rb
rename to Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/backports-3.8.0/lib/backports/2.4.0/string/match.rb
index 6299a3fb48432..9f9f49dd187ff 100644
--- a/Library/Homebrew/vendor/backports/string.rb
+++ b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/backports-3.8.0/lib/backports/2.4.0/string/match.rb
@@ -1,4 +1,3 @@
-# Taken from https://github.com/marcandre/backports/blob/v3.8.0/lib/backports/2.4.0/string/match.rb
 unless String.method_defined? :match?
   class String
     def match?(*args)
diff --git a/Library/Homebrew/vendor/plist/plist.rb b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/plist-3.3.0/lib/plist.rb
old mode 100755
new mode 100644
similarity index 74%
rename from Library/Homebrew/vendor/plist/plist.rb
rename to Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/plist-3.3.0/lib/plist.rb
index 82ecb27d28eb9..986dad4617455
--- a/Library/Homebrew/vendor/plist/plist.rb
+++ b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/plist-3.3.0/lib/plist.rb
@@ -13,9 +13,9 @@
 require 'cgi'
 require 'stringio'
 
-require_relative 'plist/generator'
-require_relative 'plist/parser'
-require_relative 'plist/version'
+require 'plist/generator'
+require 'plist/parser'
+require 'plist/version'
 
 module Plist
 end
diff --git a/Library/Homebrew/vendor/plist/plist/generator.rb b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/plist-3.3.0/lib/plist/generator.rb
old mode 100755
new mode 100644
similarity index 100%
rename from Library/Homebrew/vendor/plist/plist/generator.rb
rename to Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/plist-3.3.0/lib/plist/generator.rb
diff --git a/Library/Homebrew/vendor/plist/plist/parser.rb b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/plist-3.3.0/lib/plist/parser.rb
similarity index 100%
rename from Library/Homebrew/vendor/plist/plist/parser.rb
rename to Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/plist-3.3.0/lib/plist/parser.rb
diff --git a/Library/Homebrew/vendor/plist/plist/version.rb b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/plist-3.3.0/lib/plist/version.rb
old mode 100755
new mode 100644
similarity index 100%
rename from Library/Homebrew/vendor/plist/plist/version.rb
rename to Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/plist-3.3.0/lib/plist/version.rb
diff --git a/Library/Homebrew/vendor/macho/macho.rb b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho.rb
similarity index 100%
rename from Library/Homebrew/vendor/macho/macho.rb
rename to Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho.rb
diff --git a/Library/Homebrew/vendor/macho/macho/exceptions.rb b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/exceptions.rb
similarity index 100%
rename from Library/Homebrew/vendor/macho/macho/exceptions.rb
rename to Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/exceptions.rb
diff --git a/Library/Homebrew/vendor/macho/macho/fat_file.rb b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/fat_file.rb
similarity index 100%
rename from Library/Homebrew/vendor/macho/macho/fat_file.rb
rename to Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/fat_file.rb
diff --git a/Library/Homebrew/vendor/macho/macho/headers.rb b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/headers.rb
similarity index 100%
rename from Library/Homebrew/vendor/macho/macho/headers.rb
rename to Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/headers.rb
diff --git a/Library/Homebrew/vendor/macho/macho/load_commands.rb b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/load_commands.rb
similarity index 100%
rename from Library/Homebrew/vendor/macho/macho/load_commands.rb
rename to Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/load_commands.rb
diff --git a/Library/Homebrew/vendor/macho/macho/macho_file.rb b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/macho_file.rb
similarity index 100%
rename from Library/Homebrew/vendor/macho/macho/macho_file.rb
rename to Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/macho_file.rb
diff --git a/Library/Homebrew/vendor/macho/macho/sections.rb b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/sections.rb
similarity index 100%
rename from Library/Homebrew/vendor/macho/macho/sections.rb
rename to Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/sections.rb
diff --git a/Library/Homebrew/vendor/macho/macho/structure.rb b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/structure.rb
similarity index 100%
rename from Library/Homebrew/vendor/macho/macho/structure.rb
rename to Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/structure.rb
diff --git a/Library/Homebrew/vendor/macho/macho/tools.rb b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/tools.rb
similarity index 100%
rename from Library/Homebrew/vendor/macho/macho/tools.rb
rename to Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/tools.rb
diff --git a/Library/Homebrew/vendor/macho/macho/utils.rb b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/utils.rb
similarity index 100%
rename from Library/Homebrew/vendor/macho/macho/utils.rb
rename to Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/utils.rb
diff --git a/Library/Homebrew/vendor/macho/macho/view.rb b/Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/view.rb
similarity index 100%
rename from Library/Homebrew/vendor/macho/macho/view.rb
rename to Library/Homebrew/vendor/bundle-standalone/ruby/2.3.0/gems/ruby-macho-2.0.0/lib/macho/view.rb