diff --git a/.github/workflows/tests.yml b/.github/workflows/tests.yml
index f3f4078ce5027..12c6f8444b8f3 100644
--- a/.github/workflows/tests.yml
+++ b/.github/workflows/tests.yml
@@ -24,7 +24,7 @@ jobs:
           restore-keys: ${{ runner.os }}-rubygems-
 
       - name: Install Bundler RubyGems
-        run: brew install-bundler-gems
+        run: brew install-bundler-gems --groups=sorbet
 
       - name: Install shellcheck
         run: brew install shellcheck
@@ -60,7 +60,7 @@ jobs:
           restore-keys: ${{ runner.os }}-rubygems-
 
       - name: Install Bundler RubyGems
-        run: brew install-bundler-gems
+        run: brew install-bundler-gems --groups=sorbet
 
       - run: brew doctor
 
@@ -152,7 +152,7 @@ jobs:
       # Can't cache this because we need to check that it doesn't fail the
       # "uncommitted RubyGems" step with a cold cache.
       - name: Install Bundler RubyGems
-        run: brew install-bundler-gems
+        run: brew install-bundler-gems --groups=sorbet
 
       - name: Check for uncommitted RubyGems
         run: git diff --stat --exit-code Library/Homebrew/vendor/bundle/ruby
@@ -206,7 +206,7 @@ jobs:
           restore-keys: ${{ runner.os }}-rubygems-
 
       - name: Install Bundler RubyGems
-        run: brew install-bundler-gems
+        run: brew install-bundler-gems --groups=sorbet
 
       - name: Create parallel test log directory
         run: mkdir tests
@@ -265,7 +265,7 @@ jobs:
       # Can't cache this because we need to check that it doesn't fail the
       # "uncommitted RubyGems" step with a cold cache.
       - name: Install Bundler RubyGems
-        run: brew install-bundler-gems
+        run: brew install-bundler-gems --groups=sorbet
 
       - name: Check for uncommitted RubyGems
         run: git diff --stat --exit-code Library/Homebrew/vendor/bundle/ruby
diff --git a/Library/Homebrew/.bundle/config b/Library/Homebrew/.bundle/config
index 24c48a4c9df4d..e2c528e14d425 100644
--- a/Library/Homebrew/.bundle/config
+++ b/Library/Homebrew/.bundle/config
@@ -2,6 +2,7 @@
 BUNDLE_BIN: "false"
 BUNDLE_CLEAN: "true"
 BUNDLE_DISABLE_SHARED_GEMS: "true"
+BUNDLE_FORGET_CLI_OPTIONS: "true"
 BUNDLE_JOBS: "4"
 BUNDLE_PATH: "vendor/bundle"
 BUNDLE_RETRY: "3"
diff --git a/Library/Homebrew/.rubocop_todo.yml b/Library/Homebrew/.rubocop_todo.yml
index dc0b0f6ba9f7d..ad5c59bac70ba 100644
--- a/Library/Homebrew/.rubocop_todo.yml
+++ b/Library/Homebrew/.rubocop_todo.yml
@@ -8,6 +8,7 @@ Style/Documentation:
     - "cask/macos.rb"
     - "cli/args.rb"
     - "cli/parser.rb"
+    - "default_prefix.rb"
     - "global.rb"
     - "keg_relocate.rb"
     - "os/linux/global.rb"
diff --git a/Library/Homebrew/Gemfile b/Library/Homebrew/Gemfile
index 5c755eab6b1d5..70c9b44ba22aa 100644
--- a/Library/Homebrew/Gemfile
+++ b/Library/Homebrew/Gemfile
@@ -13,17 +13,20 @@ gem "rspec", require: false
 gem "rspec-github", require: false
 gem "rspec-its", require: false
 gem "rspec-retry", require: false
-gem "rspec-sorbet", require: false
 gem "rspec-wait", require: false
 gem "rubocop", require: false
 gem "rubocop-ast", require: false
 gem "simplecov", require: false
 gem "simplecov-cobertura", require: false
-gem "sorbet", require: false
-gem "sorbet-runtime", require: false
-gem "tapioca", require: false
 gem "warning", require: false
 
+group :sorbet, optional: true do
+  gem "rspec-sorbet", require: false
+  gem "sorbet", require: false
+  gem "sorbet-runtime", require: false
+  gem "tapioca", require: false
+end
+
 # vendored gems
 gem "activesupport"
 gem "concurrent-ruby"
diff --git a/Library/Homebrew/cli/args.rbi b/Library/Homebrew/cli/args.rbi
index 69ff5360b8024..9b4429dd77a2e 100644
--- a/Library/Homebrew/cli/args.rbi
+++ b/Library/Homebrew/cli/args.rbi
@@ -275,6 +275,9 @@ module Homebrew
 
       sig { returns(T.nilable(String)) }
       def screen_saverdir; end
+
+      sig { returns(T.nilable(T::Array[String])) }
+      def groups; end
     end
   end
 end
diff --git a/Library/Homebrew/config.rbi b/Library/Homebrew/config.rbi
new file mode 100644
index 0000000000000..2cab9bf6d521a
--- /dev/null
+++ b/Library/Homebrew/config.rbi
@@ -0,0 +1,6 @@
+# typed: strict
+
+module EnvVar
+  sig { params(env: String).returns(String) }
+  def self.[](env); end
+end
diff --git a/Library/Homebrew/default_prefix.rb b/Library/Homebrew/default_prefix.rb
new file mode 100644
index 0000000000000..4e2f6f1ee4284
--- /dev/null
+++ b/Library/Homebrew/default_prefix.rb
@@ -0,0 +1,12 @@
+# typed: true
+# frozen_string_literal: true
+
+module Homebrew
+  DEFAULT_PREFIX, DEFAULT_REPOSITORY = if OS.mac? && Hardware::CPU.arm?
+    [HOMEBREW_MACOS_ARM_DEFAULT_PREFIX, HOMEBREW_MACOS_ARM_DEFAULT_REPOSITORY]
+  elsif OS.linux? && !EnvConfig.force_homebrew_on_linux?
+    [HOMEBREW_LINUX_DEFAULT_PREFIX, HOMEBREW_LINUX_DEFAULT_REPOSITORY]
+  else
+    [HOMEBREW_DEFAULT_PREFIX, HOMEBREW_DEFAULT_REPOSITORY]
+  end.freeze
+end
diff --git a/Library/Homebrew/dev-cmd/install-bundler-gems.rb b/Library/Homebrew/dev-cmd/install-bundler-gems.rb
index 73ba1f7f49402..a5dd4d015be91 100644
--- a/Library/Homebrew/dev-cmd/install-bundler-gems.rb
+++ b/Library/Homebrew/dev-cmd/install-bundler-gems.rb
@@ -15,14 +15,19 @@ def install_bundler_gems_args
       description <<~EOS
         Install Homebrew's Bundler gems.
       EOS
+      comma_array "--groups=",
+                  description: "Installs the specified comma-separated list of gem groups (default: last used)."
 
       named_args :none
     end
   end
 
   def install_bundler_gems
-    install_bundler_gems_args.parse
+    args = install_bundler_gems_args.parse
 
-    Homebrew.install_bundler_gems!
+    # Clear previous settings. We want to fully replace - not append.
+    Homebrew::Settings.delete(:gemgroups) if args.groups
+
+    Homebrew.install_bundler_gems!(groups: args.groups || [])
   end
 end
diff --git a/Library/Homebrew/dev-cmd/tests.rb b/Library/Homebrew/dev-cmd/tests.rb
index 3638033b45456..f35117e56e951 100644
--- a/Library/Homebrew/dev-cmd/tests.rb
+++ b/Library/Homebrew/dev-cmd/tests.rb
@@ -39,15 +39,17 @@ def tests_args
   def tests
     args = tests_args.parse
 
-    Homebrew.install_bundler_gems!
+    Homebrew.install_bundler_gems!(groups: ["sorbet"])
 
     require "byebug" if args.byebug?
 
     HOMEBREW_LIBRARY_PATH.cd do
       # Cleanup any unwanted user configuration.
-      allowed_test_env = [
-        "HOMEBREW_GITHUB_API_TOKEN",
-        "HOMEBREW_TEMP",
+      allowed_test_env = %w[
+        HOMEBREW_GITHUB_API_TOKEN
+        HOMEBREW_CACHE
+        HOMEBREW_LOGS
+        HOMEBREW_TEMP
       ]
       Homebrew::EnvConfig::ENVS.keys.map(&:to_s).each do |env|
         next if allowed_test_env.include?(env)
diff --git a/Library/Homebrew/dev-cmd/typecheck.rb b/Library/Homebrew/dev-cmd/typecheck.rb
index 6826b4188402d..daa595491e682 100644
--- a/Library/Homebrew/dev-cmd/typecheck.rb
+++ b/Library/Homebrew/dev-cmd/typecheck.rb
@@ -51,7 +51,7 @@ def typecheck
 
     args = typecheck_args.parse
 
-    Homebrew.install_bundler_gems!
+    Homebrew.install_bundler_gems!(groups: ["sorbet"])
 
     HOMEBREW_LIBRARY_PATH.cd do
       if args.update?
diff --git a/Library/Homebrew/dev-cmd/vendor-gems.rb b/Library/Homebrew/dev-cmd/vendor-gems.rb
index 56e1de3a48d3d..6a8b62f5a85dc 100644
--- a/Library/Homebrew/dev-cmd/vendor-gems.rb
+++ b/Library/Homebrew/dev-cmd/vendor-gems.rb
@@ -29,6 +29,8 @@ def vendor_gems
 
     Homebrew.install_bundler!
 
+    ENV["BUNDLE_WITH"] = "sorbet"
+
     ohai "cd #{HOMEBREW_LIBRARY_PATH}"
     HOMEBREW_LIBRARY_PATH.cd do
       if args.update
diff --git a/Library/Homebrew/diagnostic.rb b/Library/Homebrew/diagnostic.rb
index b8d45ae666f0e..683a2a5bd094a 100644
--- a/Library/Homebrew/diagnostic.rb
+++ b/Library/Homebrew/diagnostic.rb
@@ -149,7 +149,9 @@ def examine_git_origin(repository_path, desired_origin)
 
       def broken_tap(tap)
         return unless Utils::Git.available?
-        return unless HOMEBREW_REPOSITORY.git?
+
+        repo = HOMEBREW_REPOSITORY.dup.extend(GitRepositoryExtension)
+        return unless repo.git?
 
         message = <<~EOS
           #{tap.full_name} was not tapped properly! Run:
@@ -161,7 +163,7 @@ def broken_tap(tap)
 
         tap_head = tap.git_head
         return message if tap_head.blank?
-        return if tap_head != HOMEBREW_REPOSITORY.git_head
+        return if tap_head != repo.git_head
 
         message
       end
@@ -574,7 +576,8 @@ def check_git_newline_settings
       end
 
       def check_brew_git_origin
-        examine_git_origin(HOMEBREW_REPOSITORY, Homebrew::EnvConfig.brew_git_remote)
+        repo = HOMEBREW_REPOSITORY.dup.extend(GitRepositoryExtension)
+        examine_git_origin(repo, Homebrew::EnvConfig.brew_git_remote)
       end
 
       def check_coretap_integrity
diff --git a/Library/Homebrew/global.rb b/Library/Homebrew/global.rb
index d668dac471d6a..15454796e1a4c 100644
--- a/Library/Homebrew/global.rb
+++ b/Library/Homebrew/global.rb
@@ -1,22 +1,16 @@
 # typed: false
 # frozen_string_literal: true
 
-require_relative "load_path"
+require_relative "startup"
 
 require "English"
 require "fileutils"
 require "json"
 require "json/add/exception"
-require "pathname"
 require "ostruct"
 require "pp"
 require "forwardable"
 
-require "rbconfig"
-
-RUBY_PATH = Pathname.new(RbConfig.ruby).freeze
-RUBY_BIN = RUBY_PATH.dirname.freeze
-
 # Only require "core_ext" here to ensure we're only requiring the minimum of
 # what we need.
 require "active_support/core_ext/object/blank"
@@ -72,27 +66,15 @@
   %r[https://github\.com/([\w-]+)/([\w-]+)?/(?:pull/(\d+)|commit/[0-9a-fA-F]{4,40})].freeze
 HOMEBREW_BOTTLES_EXTNAME_REGEX = /\.([a-z0-9_]+)\.bottle\.(?:(\d+)\.)?tar\.gz$/.freeze
 
-require "utils/sorbet"
-
 require "env_config"
 require "compat/early" unless Homebrew::EnvConfig.no_compat?
 require "os"
 require "messages"
+require "default_prefix"
 
 module Homebrew
   extend FileUtils
 
-  remove_const :DEFAULT_PREFIX if defined?(DEFAULT_PREFIX)
-  remove_const :DEFAULT_REPOSITORY if defined?(DEFAULT_REPOSITORY)
-
-  DEFAULT_PREFIX, DEFAULT_REPOSITORY = if OS.mac? && Hardware::CPU.arm?
-    [HOMEBREW_MACOS_ARM_DEFAULT_PREFIX, HOMEBREW_MACOS_ARM_DEFAULT_REPOSITORY]
-  elsif OS.linux? && !EnvConfig.force_homebrew_on_linux?
-    [HOMEBREW_LINUX_DEFAULT_PREFIX, HOMEBREW_LINUX_DEFAULT_REPOSITORY]
-  else
-    [HOMEBREW_DEFAULT_PREFIX, HOMEBREW_DEFAULT_REPOSITORY]
-  end.freeze
-
   DEFAULT_CELLAR = "#{DEFAULT_PREFIX}/Cellar"
   DEFAULT_MACOS_CELLAR = "#{HOMEBREW_DEFAULT_PREFIX}/Cellar"
   DEFAULT_MACOS_ARM_CELLAR = "#{HOMEBREW_MACOS_ARM_DEFAULT_PREFIX}/Cellar"
@@ -124,8 +106,8 @@ def auditing?
   end
 end
 
-require "config"
 require "context"
+require "extend/git_repository"
 require "extend/pathname"
 require "extend/predicable"
 require "extend/module"
diff --git a/Library/Homebrew/rubocops.rb b/Library/Homebrew/rubocops.rb
index 3190abc5863b2..3e5daa64c331e 100644
--- a/Library/Homebrew/rubocops.rb
+++ b/Library/Homebrew/rubocops.rb
@@ -1,40 +1,6 @@
 # typed: strict
 # frozen_string_literal: true
 
-require_relative "load_path"
+require_relative "standalone"
 
-require "active_support/core_ext/array/conversions"
-
-require "utils/sorbet"
-
-require "rubocop-performance"
-require "rubocop-rails"
-require "rubocop-rspec"
-require "rubocop-sorbet"
-
-require "rubocops/io_read"
-require "rubocops/shell_commands"
-
-require "rubocops/formula_desc"
-require "rubocops/components_order"
-require "rubocops/components_redundancy"
-require "rubocops/dependency_order"
-require "rubocops/homepage"
-require "rubocops/text"
-require "rubocops/caveats"
-require "rubocops/checksum"
-require "rubocops/patches"
-require "rubocops/conflicts"
-require "rubocops/options"
-require "rubocops/urls"
-require "rubocops/lines"
-require "rubocops/livecheck"
-require "rubocops/class"
-require "rubocops/uses_from_macos"
-require "rubocops/files"
-require "rubocops/keg_only"
-require "rubocops/version"
-require "rubocops/deprecate_disable"
-require "rubocops/bottle"
-
-require "rubocops/rubocop-cask"
+require "rubocops/all"
diff --git a/Library/Homebrew/rubocops/all.rb b/Library/Homebrew/rubocops/all.rb
new file mode 100644
index 0000000000000..40bf1eab43681
--- /dev/null
+++ b/Library/Homebrew/rubocops/all.rb
@@ -0,0 +1,36 @@
+# typed: strict
+# frozen_string_literal: true
+
+require "active_support/core_ext/array/conversions"
+
+require "rubocop-performance"
+require "rubocop-rails"
+require "rubocop-rspec"
+require "rubocop-sorbet"
+
+require_relative "io_read"
+require_relative "shell_commands"
+
+require_relative "formula_desc"
+require_relative "components_order"
+require_relative "components_redundancy"
+require_relative "dependency_order"
+require_relative "homepage"
+require_relative "text"
+require_relative "caveats"
+require_relative "checksum"
+require_relative "patches"
+require_relative "conflicts"
+require_relative "options"
+require_relative "urls"
+require_relative "lines"
+require_relative "livecheck"
+require_relative "class"
+require_relative "uses_from_macos"
+require_relative "files"
+require_relative "keg_only"
+require_relative "version"
+require_relative "deprecate_disable"
+require_relative "bottle"
+
+require_relative "rubocop-cask"
diff --git a/Library/Homebrew/rubocops/rubocop-cask.rb b/Library/Homebrew/rubocops/rubocop-cask.rb
index 3e0a2c457865b..4dac4d062fc6c 100644
--- a/Library/Homebrew/rubocops/rubocop-cask.rb
+++ b/Library/Homebrew/rubocops/rubocop-cask.rb
@@ -3,17 +3,17 @@
 
 require "rubocop"
 
-require "rubocops/cask/constants/stanza"
+require_relative "cask/constants/stanza"
 
-require "rubocops/cask/ast/stanza"
-require "rubocops/cask/ast/cask_header"
-require "rubocops/cask/ast/cask_block"
-require "rubocops/cask/extend/string"
-require "rubocops/cask/extend/node"
-require "rubocops/cask/mixin/cask_help"
-require "rubocops/cask/mixin/on_homepage_stanza"
-require "rubocops/cask/desc"
-require "rubocops/cask/homepage_url_trailing_slash"
-require "rubocops/cask/no_dsl_version"
-require "rubocops/cask/stanza_order"
-require "rubocops/cask/stanza_grouping"
+require_relative "cask/ast/stanza"
+require_relative "cask/ast/cask_header"
+require_relative "cask/ast/cask_block"
+require_relative "cask/extend/string"
+require_relative "cask/extend/node"
+require_relative "cask/mixin/cask_help"
+require_relative "cask/mixin/on_homepage_stanza"
+require_relative "cask/desc"
+require_relative "cask/homepage_url_trailing_slash"
+require_relative "cask/no_dsl_version"
+require_relative "cask/stanza_order"
+require_relative "cask/stanza_grouping"
diff --git a/Library/Homebrew/settings.rb b/Library/Homebrew/settings.rb
index 8a58e94199fe0..f04820eef2c06 100644
--- a/Library/Homebrew/settings.rb
+++ b/Library/Homebrew/settings.rb
@@ -1,26 +1,25 @@
 # typed: true
 # frozen_string_literal: true
 
-require "system_command"
+require "utils/popen"
 
 module Homebrew
   # Helper functions for reading and writing settings.
   #
   # @api private
   module Settings
-    extend T::Sig
-    include SystemCommand::Mixin
-
     module_function
 
-    sig { params(setting: T.any(String, Symbol), repo: Pathname).returns(T.nilable(String)) }
     def read(setting, repo: HOMEBREW_REPOSITORY)
       return unless (repo/".git/config").exist?
 
-      system_command("git", args: ["config", "--get", "homebrew.#{setting}"], chdir: repo).stdout.chomp.presence
+      value = Utils.popen_read("git", "-C", repo.to_s, "config", "--get", "homebrew.#{setting}").chomp
+
+      return if value.strip.empty?
+
+      value
     end
 
-    sig { params(setting: T.any(String, Symbol), value: T.any(String, T::Boolean), repo: Pathname).void }
     def write(setting, value, repo: HOMEBREW_REPOSITORY)
       return unless (repo/".git/config").exist?
 
@@ -28,16 +27,15 @@ def write(setting, value, repo: HOMEBREW_REPOSITORY)
 
       return if read(setting, repo: repo) == value
 
-      system_command! "git", args: ["config", "--replace-all", "homebrew.#{setting}", value], chdir: repo
+      Kernel.system("git", "-C", repo.to_s, "config", "--replace-all", "homebrew.#{setting}", value, exception: true)
     end
 
-    sig { params(setting: T.any(String, Symbol), repo: Pathname).void }
     def delete(setting, repo: HOMEBREW_REPOSITORY)
       return unless (repo/".git/config").exist?
 
       return if read(setting, repo: repo).blank?
 
-      system_command! "git", args: ["config", "--unset-all", "homebrew.#{setting}"], chdir: repo
+      Kernel.system("git", "-C", repo.to_s, "config", "--unset-all", "homebrew.#{setting}", exception: true)
     end
   end
 end
diff --git a/Library/Homebrew/settings.rbi b/Library/Homebrew/settings.rbi
index 289622fd41958..d902c06acb7c8 100644
--- a/Library/Homebrew/settings.rbi
+++ b/Library/Homebrew/settings.rbi
@@ -3,5 +3,14 @@
 module Homebrew
   module Settings
     include Kernel
+
+    sig { params(setting: T.any(String, Symbol), repo: Pathname).returns(T.nilable(String)) }
+    def read(setting, repo: HOMEBREW_REPOSITORY); end
+
+    sig { params(setting: T.any(String, Symbol), value: T.any(String, T::Boolean), repo: Pathname).void }
+    def write(setting, value, repo: HOMEBREW_REPOSITORY); end
+
+    sig { params(setting: T.any(String, Symbol), repo: Pathname).void }
+    def delete(setting, repo: HOMEBREW_REPOSITORY); end
   end
 end
diff --git a/Library/Homebrew/standalone.rb b/Library/Homebrew/standalone.rb
new file mode 100644
index 0000000000000..cb540077a1a29
--- /dev/null
+++ b/Library/Homebrew/standalone.rb
@@ -0,0 +1,7 @@
+# typed: true
+# frozen_string_literal: true
+
+# This file should be the first `require` in all entrypoints outside the `brew` environment.
+
+require_relative "standalone/load_path"
+require_relative "standalone/sorbet"
diff --git a/Library/Homebrew/load_path.rb b/Library/Homebrew/standalone/load_path.rb
similarity index 82%
rename from Library/Homebrew/load_path.rb
rename to Library/Homebrew/standalone/load_path.rb
index a5c65fb680876..ff7daed613d06 100644
--- a/Library/Homebrew/load_path.rb
+++ b/Library/Homebrew/standalone/load_path.rb
@@ -3,13 +3,13 @@
 
 require "pathname"
 
-HOMEBREW_LIBRARY_PATH = Pathname(__dir__).realpath.freeze
+HOMEBREW_LIBRARY_PATH = Pathname(__dir__).parent.realpath.freeze
 
-require_relative "utils/gems"
+require_relative "../utils/gems"
 Homebrew.setup_gem_environment!(setup_path: false)
 
 $LOAD_PATH.push HOMEBREW_LIBRARY_PATH.to_s unless $LOAD_PATH.include?(HOMEBREW_LIBRARY_PATH.to_s)
-require_relative "vendor/bundle/bundler/setup"
+require_relative "../vendor/bundle/bundler/setup"
 $LOAD_PATH.uniq!
 
 # Block any gem loading by bypassing rubygem's `require`.
@@ -21,5 +21,3 @@
   Kernel.send(:define_method, :require, Kernel.instance_method(:gem_original_require))
   Kernel.send(:private, :require)
 end
-
-require_relative "homebrew_bootsnap"
diff --git a/Library/Homebrew/standalone/sorbet.rb b/Library/Homebrew/standalone/sorbet.rb
new file mode 100644
index 0000000000000..8576c7ad0ddd0
--- /dev/null
+++ b/Library/Homebrew/standalone/sorbet.rb
@@ -0,0 +1,11 @@
+# typed: true
+# frozen_string_literal: true
+
+# Explicitly prevent `sorbet-runtime` from being loaded.
+def gem(name, *)
+  raise Gem::LoadError if name == "sorbet-runtime"
+
+  super
+end
+
+require "sorbet-runtime-stub"
diff --git a/Library/Homebrew/startup.rb b/Library/Homebrew/startup.rb
new file mode 100644
index 0000000000000..d08f5420cf765
--- /dev/null
+++ b/Library/Homebrew/startup.rb
@@ -0,0 +1,10 @@
+# typed: true
+# frozen_string_literal: true
+
+# This file should be the first `require` in all entrypoints of `brew`.
+
+require_relative "standalone/load_path"
+require_relative "startup/ruby_path"
+require "startup/config"
+require_relative "startup/bootsnap"
+require_relative "startup/sorbet"
diff --git a/Library/Homebrew/homebrew_bootsnap.rb b/Library/Homebrew/startup/bootsnap.rb
similarity index 100%
rename from Library/Homebrew/homebrew_bootsnap.rb
rename to Library/Homebrew/startup/bootsnap.rb
diff --git a/Library/Homebrew/config.rb b/Library/Homebrew/startup/config.rb
similarity index 90%
rename from Library/Homebrew/config.rb
rename to Library/Homebrew/startup/config.rb
index 4369b95616ad4..29d3088bff4f6 100644
--- a/Library/Homebrew/config.rb
+++ b/Library/Homebrew/startup/config.rb
@@ -12,9 +12,6 @@ class MissingEnvironmentVariables < RuntimeError; end
 #
 # @api private
 module EnvVar
-  extend T::Sig
-
-  sig { params(env: String).returns(String) }
   def self.[](env)
     raise MissingEnvironmentVariables, "#{env} was not exported!" unless ENV[env]
 
@@ -22,15 +19,11 @@ def self.[](env)
   end
 end
 
-require "extend/git_repository"
-
 # Where we link under
 HOMEBREW_PREFIX = Pathname(EnvVar["HOMEBREW_PREFIX"]).freeze
 
 # Where `.git` is found
-HOMEBREW_REPOSITORY = Pathname(EnvVar["HOMEBREW_REPOSITORY"])
-                      .extend(GitRepositoryExtension)
-                      .freeze
+HOMEBREW_REPOSITORY = Pathname(EnvVar["HOMEBREW_REPOSITORY"]).freeze
 
 # Where we store most of Homebrew, taps, and various metadata
 HOMEBREW_LIBRARY = Pathname(EnvVar["HOMEBREW_LIBRARY"]).freeze
diff --git a/Library/Homebrew/startup/ruby_path.rb b/Library/Homebrew/startup/ruby_path.rb
new file mode 100644
index 0000000000000..e9a7a634fbda2
--- /dev/null
+++ b/Library/Homebrew/startup/ruby_path.rb
@@ -0,0 +1,7 @@
+# typed: true
+# frozen_string_literal: true
+
+require "rbconfig"
+
+RUBY_PATH = Pathname.new(RbConfig.ruby).freeze
+RUBY_BIN = RUBY_PATH.dirname.freeze
diff --git a/Library/Homebrew/startup/sorbet.rb b/Library/Homebrew/startup/sorbet.rb
new file mode 100644
index 0000000000000..6005bbe088589
--- /dev/null
+++ b/Library/Homebrew/startup/sorbet.rb
@@ -0,0 +1,10 @@
+# typed: true
+# frozen_string_literal: true
+
+if ENV["HOMEBREW_SORBET_RUNTIME"]
+  # This is only supported under the brew environment.
+  Homebrew.install_bundler_gems!(groups: ["sorbet"])
+  require "sorbet-runtime"
+else
+  require "standalone/sorbet"
+end
diff --git a/Library/Homebrew/style.rb b/Library/Homebrew/style.rb
index bba9ead69881a..c802ad087c0b6 100644
--- a/Library/Homebrew/style.rb
+++ b/Library/Homebrew/style.rb
@@ -85,7 +85,7 @@ def run_rubocop(files, output_type,
         require "rubocop"
       end
 
-      require "rubocops"
+      require "rubocops/all"
 
       args = %w[
         --force-exclusion
diff --git a/Library/Homebrew/system_config.rb b/Library/Homebrew/system_config.rb
index 14f16388ca4f9..8912abf2fc14a 100644
--- a/Library/Homebrew/system_config.rb
+++ b/Library/Homebrew/system_config.rb
@@ -32,19 +32,24 @@ def clang_build
       end
     end
 
+    sig { returns(Pathname) }
+    def homebrew_repo
+      HOMEBREW_REPOSITORY.dup.extend(GitRepositoryExtension)
+    end
+
     sig { returns(String) }
     def head
-      HOMEBREW_REPOSITORY.git_head || "(none)"
+      homebrew_repo.git_head || "(none)"
     end
 
     sig { returns(String) }
     def last_commit
-      HOMEBREW_REPOSITORY.git_last_commit || "never"
+      homebrew_repo.git_last_commit || "never"
     end
 
     sig { returns(String) }
     def origin
-      HOMEBREW_REPOSITORY.git_origin || "(none)"
+      homebrew_repo.git_origin || "(none)"
     end
 
     sig { returns(String) }
diff --git a/Library/Homebrew/tap_constants.rb b/Library/Homebrew/tap_constants.rb
index 10e167b2a2895..b9edb7afebc43 100644
--- a/Library/Homebrew/tap_constants.rb
+++ b/Library/Homebrew/tap_constants.rb
@@ -1,8 +1,6 @@
 # typed: true
 # frozen_string_literal: true
 
-require "config"
-
 # Match taps' formulae, e.g. `someuser/sometap/someformula`
 HOMEBREW_TAP_FORMULA_REGEX = %r{^([\w-]+)/([\w-]+)/([\w+-.@]+)$}.freeze
 # Match taps' casks, e.g. `someuser/sometap/somecask`
diff --git a/Library/Homebrew/test/cmd/home_spec.rb b/Library/Homebrew/test/cmd/home_spec.rb
index 57c6eb70b0f51..063846c3346f3 100644
--- a/Library/Homebrew/test/cmd/home_spec.rb
+++ b/Library/Homebrew/test/cmd/home_spec.rb
@@ -2,7 +2,6 @@
 # frozen_string_literal: true
 
 require "cmd/shared_examples/args_parse"
-require "support/lib/config"
 
 describe "brew home" do
   let(:testballhome_homepage) {
diff --git a/Library/Homebrew/test/support/lib/default_prefix.rb b/Library/Homebrew/test/support/lib/default_prefix.rb
new file mode 100644
index 0000000000000..e912bd4831520
--- /dev/null
+++ b/Library/Homebrew/test/support/lib/default_prefix.rb
@@ -0,0 +1,8 @@
+# typed: true
+# frozen_string_literal: true
+
+module Homebrew
+  # For testing's sake always assume the default prefix
+  DEFAULT_PREFIX = HOMEBREW_PREFIX.to_s.freeze
+  DEFAULT_REPOSITORY = HOMEBREW_REPOSITORY.to_s.freeze
+end
diff --git a/Library/Homebrew/test/support/lib/config.rb b/Library/Homebrew/test/support/lib/startup/config.rb
similarity index 84%
rename from Library/Homebrew/test/support/lib/config.rb
rename to Library/Homebrew/test/support/lib/startup/config.rb
index 9e11210c39f95..ea9aad2897b4a 100644
--- a/Library/Homebrew/test/support/lib/config.rb
+++ b/Library/Homebrew/test/support/lib/startup/config.rb
@@ -3,8 +3,6 @@
 
 raise "HOMEBREW_BREW_FILE was not exported! Please call bin/brew directly!" unless ENV["HOMEBREW_BREW_FILE"]
 
-require "pathname"
-
 HOMEBREW_BREW_FILE = Pathname.new(ENV["HOMEBREW_BREW_FILE"]).freeze
 
 TEST_TMPDIR = ENV.fetch("HOMEBREW_TEST_TMPDIR") do |k|
@@ -23,11 +21,9 @@
 # Where external data that has been incorporated into Homebrew is stored
 HOMEBREW_DATA_PATH = (HOMEBREW_LIBRARY_PATH/"data").freeze
 
-require "extend/git_repository"
-
 # Paths redirected to a temporary directory and wiped at the end of the test run
 HOMEBREW_PREFIX        = (Pathname(TEST_TMPDIR)/"prefix").freeze
-HOMEBREW_REPOSITORY    = HOMEBREW_PREFIX.dup.extend(GitRepositoryExtension).freeze
+HOMEBREW_REPOSITORY    = HOMEBREW_PREFIX.dup.freeze
 HOMEBREW_LIBRARY       = (HOMEBREW_REPOSITORY/"Library").freeze
 HOMEBREW_CACHE         = (HOMEBREW_PREFIX.parent/"cache").freeze
 HOMEBREW_CACHE_FORMULA = (HOMEBREW_PREFIX.parent/"formula_cache").freeze
@@ -52,12 +48,3 @@
 
 TEST_SHA1   = "deadbeefdeadbeefdeadbeefdeadbeefdeadbeef"
 TEST_SHA256 = "deadbeefdeadbeefdeadbeefdeadbeefdeadbeefdeadbeefdeadbeefdeadbeef"
-
-# For testing's sake always assume the default prefix
-module Homebrew
-  remove_const :DEFAULT_PREFIX if defined?(DEFAULT_PREFIX)
-  DEFAULT_PREFIX = HOMEBREW_PREFIX.to_s.freeze
-
-  remove_const :DEFAULT_REPOSITORY if defined?(DEFAULT_REPOSITORY)
-  DEFAULT_REPOSITORY = HOMEBREW_REPOSITORY.to_s.freeze
-end
diff --git a/Library/Homebrew/utils/gems.rb b/Library/Homebrew/utils/gems.rb
index bc2337834c4c6..0eaada3c8e477 100644
--- a/Library/Homebrew/utils/gems.rb
+++ b/Library/Homebrew/utils/gems.rb
@@ -52,7 +52,7 @@ def odie_if_defined(message)
 
   def setup_gem_environment!(gem_home: nil, gem_bindir: nil, setup_path: true)
     # Match where our bundler gems are.
-    gem_home ||= "#{ENV["HOMEBREW_LIBRARY"]}/Homebrew/vendor/bundle/ruby/#{RbConfig::CONFIG["ruby_version"]}"
+    gem_home ||= "#{HOMEBREW_LIBRARY_PATH}/vendor/bundle/ruby/#{RbConfig::CONFIG["ruby_version"]}"
     Gem.paths = {
       "GEM_HOME" => gem_home,
       "GEM_PATH" => gem_home,
@@ -128,23 +128,34 @@ def install_bundler!
     )
   end
 
-  def install_bundler_gems!(only_warn_on_failure: false, setup_path: true)
+  def install_bundler_gems!(only_warn_on_failure: false, setup_path: true, groups: [])
     old_path = ENV["PATH"]
     old_gem_path = ENV["GEM_PATH"]
     old_gem_home = ENV["GEM_HOME"]
     old_bundle_gemfile = ENV["BUNDLE_GEMFILE"]
+    old_bundle_with = ENV["BUNDLE_WITH"]
 
     install_bundler!
 
+    require "settings"
+
+    # Combine the passed groups with the ones stored in settings
+    groups |= (Homebrew::Settings.read(:gemgroups)&.split(";") || [])
+    groups.sort!
+
     ENV["BUNDLE_GEMFILE"] = File.join(ENV.fetch("HOMEBREW_LIBRARY"), "Homebrew", "Gemfile")
-    @bundle_installed ||= begin
+    ENV["BUNDLE_WITH"] = groups.join(" ")
+
+    if @bundle_installed_groups != groups
       bundle = File.join(find_in_path("bundle"), "bundle")
       bundle_check_output = `#{bundle} check 2>&1`
       bundle_check_failed = !$CHILD_STATUS.success?
 
       # for some reason sometimes the exit code lies so check the output too.
-      if bundle_check_failed || bundle_check_output.include?("Install missing gems")
-        unless system bundle, "install"
+      bundle_installed = if bundle_check_failed || bundle_check_output.include?("Install missing gems")
+        if system bundle, "install"
+          true
+        else
           message = <<~EOS
             failed to run `#{bundle} install`!
           EOS
@@ -153,10 +164,16 @@ def install_bundler_gems!(only_warn_on_failure: false, setup_path: true)
           else
             odie_if_defined message
           end
+          false
         end
       else
         true
       end
+
+      if bundle_installed
+        Homebrew::Settings.write(:gemgroups, groups.join(";"))
+        @bundle_installed_groups = groups
+      end
     end
 
     setup_gem_environment!
@@ -167,6 +184,7 @@ def install_bundler_gems!(only_warn_on_failure: false, setup_path: true)
       ENV["GEM_PATH"] = old_gem_path
       ENV["GEM_HOME"] = old_gem_home
       ENV["BUNDLE_GEMFILE"] = old_bundle_gemfile
+      ENV["BUNDLE_WITH"] = old_bundle_with
     end
   end
 end
diff --git a/Library/Homebrew/utils/gems.rbi b/Library/Homebrew/utils/gems.rbi
index 55bdcc1114cd9..746bceef1d4bb 100644
--- a/Library/Homebrew/utils/gems.rbi
+++ b/Library/Homebrew/utils/gems.rbi
@@ -22,6 +22,6 @@ module Homebrew
   sig { void }
   def install_bundler!; end
 
-  sig { params(only_warn_on_failure: T::Boolean, setup_path: T::Boolean).void }
-  def install_bundler_gems!(only_warn_on_failure: false, setup_path: false); end
+  sig { params(only_warn_on_failure: T::Boolean, setup_path: T::Boolean, groups: T::Array[String]).void }
+  def install_bundler_gems!(only_warn_on_failure: false, setup_path: false, groups: []); end
 end
diff --git a/Library/Homebrew/utils/rubocop.rb b/Library/Homebrew/utils/rubocop.rb
index ae6050ddd0f38..35db8717bdd47 100755
--- a/Library/Homebrew/utils/rubocop.rb
+++ b/Library/Homebrew/utils/rubocop.rb
@@ -2,9 +2,7 @@
 # typed: false
 # frozen_string_literal: true
 
-require_relative "gems"
-Homebrew.setup_gem_environment!
-
+require_relative "../standalone"
 require_relative "../warnings"
 
 Warnings.ignore :parser_syntax do
diff --git a/Library/Homebrew/utils/sorbet.rb b/Library/Homebrew/utils/sorbet.rb
deleted file mode 100644
index aaf7f223fd5f7..0000000000000
--- a/Library/Homebrew/utils/sorbet.rb
+++ /dev/null
@@ -1,16 +0,0 @@
-# typed: true
-# frozen_string_literal: true
-
-if ENV["HOMEBREW_SORBET_RUNTIME"]
-  Homebrew.install_bundler_gems!
-  require "sorbet-runtime"
-else
-  # Explicitly prevent `sorbet-runtime` from being loaded.
-  def gem(name, *)
-    raise Gem::LoadError if name == "sorbet-runtime"
-
-    super
-  end
-
-  require "sorbet-runtime-stub"
-end