diff --git a/.github/workflows/tests.yml b/.github/workflows/tests.yml
index 96d599fc2e..753b55289e 100644
--- a/.github/workflows/tests.yml
+++ b/.github/workflows/tests.yml
@@ -31,7 +31,7 @@ jobs:
         uses: Homebrew/actions/setup-homebrew@master
 
       - name: Cache Bundler RubyGems
-        uses: actions/cache@v1
+        uses: actions/cache@v3
         with:
           path: ${{ steps.set-up-homebrew.outputs.gems-path }}
           key: ${{ runner.os }}-rubygems-${{ steps.set-up-homebrew.outputs.gems-hash }}
@@ -73,7 +73,7 @@ jobs:
         uses: Homebrew/actions/setup-homebrew@master
 
       - name: Cache Bundler RubyGems
-        uses: actions/cache@v1
+        uses: actions/cache@v3
         with:
           path: ${{ steps.set-up-homebrew.outputs.gems-path }}
           key: ${{ runner.os }}-rubygems-${{ steps.set-up-homebrew.outputs.gems-hash }}
@@ -231,7 +231,7 @@ jobs:
         uses: Homebrew/actions/setup-homebrew@master
 
       - name: Cache Bundler RubyGems
-        uses: actions/cache@v1
+        uses: actions/cache@v3
         with:
           path: ${{ steps.set-up-homebrew.outputs.gems-path }}
           key: ${{ runner.os }}-rubygems-${{ steps.set-up-homebrew.outputs.gems-hash }}
@@ -276,7 +276,7 @@ jobs:
           HOMEBREW_NO_INSTALL_FROM_API: 1
 
       - name: Cache Bundler RubyGems
-        uses: actions/cache@v1
+        uses: actions/cache@v3
         with:
           path: ${{ steps.set-up-homebrew.outputs.gems-path }}
           key: ${{ runner.os }}-rubygems-${{ steps.set-up-homebrew.outputs.gems-hash }}
@@ -289,7 +289,7 @@ jobs:
         run: mkdir tests
 
       - name: Cache parallel tests log
-        uses: actions/cache@v1
+        uses: actions/cache@v3
         with:
           path: tests
           key: ${{ runner.os }}-${{ matrix.test-flags }}-parallel_runtime_rspec-${{ github.sha }}
diff --git a/.github/workflows/triage.yml b/.github/workflows/triage.yml
index 75c60d1c42..1c9d6ca93e 100644
--- a/.github/workflows/triage.yml
+++ b/.github/workflows/triage.yml
@@ -23,7 +23,7 @@ jobs:
     steps:
       - name: Re-run this workflow
         if: github.event_name == 'schedule' || github.event.action == 'closed'
-        uses: reitermarkus/rerun-workflow@1a15891377b6667377207cdd85b628b79ebd6f81
+        uses: reitermarkus/rerun-workflow@7381e98aa2bc4464acef4b60ade8d1d1d90e6e65
         with:
           token: ${{ secrets.HOMEBREW_GITHUB_PUBLIC_REPO_TOKEN }}
           continuous-label: waiting for feedback
diff --git a/Library/Homebrew/Gemfile b/Library/Homebrew/Gemfile
index 1a5f5d8383..79cb2bcdaa 100644
--- a/Library/Homebrew/Gemfile
+++ b/Library/Homebrew/Gemfile
@@ -28,6 +28,7 @@ gem "rubocop", require: false
 gem "rubocop-ast", require: false
 gem "simplecov", require: false
 gem "simplecov-cobertura", require: false
+gem "stackprof", require: false
 gem "warning", require: false
 
 group :sorbet, optional: true do
diff --git a/Library/Homebrew/Gemfile.lock b/Library/Homebrew/Gemfile.lock
index 37c6a02ec4..fd3156a293 100644
--- a/Library/Homebrew/Gemfile.lock
+++ b/Library/Homebrew/Gemfile.lock
@@ -188,6 +188,7 @@ GEM
       sorbet (>= 0.5.9204)
       sorbet-runtime (>= 0.5.9204)
       thor (>= 0.19.2)
+    stackprof (0.2.24)
     tapioca (0.7.3)
       bundler (>= 1.17.3)
       pry (>= 0.12.2)
@@ -257,6 +258,7 @@ DEPENDENCIES
   sorbet-runtime
   sorbet-static-and-runtime
   spoom
+  stackprof
   tapioca
   warning
 
diff --git a/Library/Homebrew/brew.rb b/Library/Homebrew/brew.rb
index 76f653aad4..6f185bc216 100644
--- a/Library/Homebrew/brew.rb
+++ b/Library/Homebrew/brew.rb
@@ -1,6 +1,7 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
+# `HOMEBREW_STACKPROF` should be set via `brew prof --stackprof`, not manually.
 if ENV["HOMEBREW_STACKPROF"]
   require "rubygems"
   require "stackprof"
@@ -35,8 +36,8 @@ begin
   empty_argv = ARGV.empty?
   help_flag_list = %w[-h --help --usage -?]
   help_flag = !ENV["HOMEBREW_HELP"].nil?
-  help_cmd_index = nil
-  cmd = nil
+  help_cmd_index = T.let(nil, T.nilable(Integer))
+  cmd = T.let(nil, T.nilable(String))
 
   ARGV.each_with_index do |arg, i|
     break if help_flag && cmd
@@ -64,7 +65,7 @@ begin
   path.prepend(HOMEBREW_SHIMS_PATH/"shared")
   homebrew_path.prepend(HOMEBREW_SHIMS_PATH/"shared")
 
-  ENV["PATH"] = path
+  ENV["PATH"] = path.to_s
 
   require "commands"
   require "settings"
@@ -76,7 +77,7 @@ begin
     homebrew_path.append(Tap.cmd_directories)
 
     # External commands expect a normal PATH
-    ENV["PATH"] = homebrew_path
+    ENV["PATH"] = homebrew_path.to_s
   end
 
   # Usage instructions should be displayed if and only if one of:
diff --git a/Library/Homebrew/cask/artifact/abstract_uninstall.rb b/Library/Homebrew/cask/artifact/abstract_uninstall.rb
index 2635bd79d1..7b4d522a7a 100644
--- a/Library/Homebrew/cask/artifact/abstract_uninstall.rb
+++ b/Library/Homebrew/cask/artifact/abstract_uninstall.rb
@@ -6,8 +6,6 @@ require "timeout"
 require "utils/user"
 require "cask/artifact/abstract_artifact"
 require "cask/pkg"
-require "extend/hash_validator"
-using HashValidator
 
 module Cask
   module Artifact
@@ -38,7 +36,7 @@ module Cask
       attr_reader :directives
 
       def initialize(cask, directives)
-        directives.assert_valid_keys!(*ORDERED_DIRECTIVES)
+        directives.assert_valid_keys(*ORDERED_DIRECTIVES)
 
         super(cask, **directives)
         directives[:signal] = Array(directives[:signal]).flatten.each_slice(2).to_a
diff --git a/Library/Homebrew/cask/artifact/artifact.rb b/Library/Homebrew/cask/artifact/artifact.rb
index 705cc4d18a..a3b25a5972 100644
--- a/Library/Homebrew/cask/artifact/artifact.rb
+++ b/Library/Homebrew/cask/artifact/artifact.rb
@@ -3,9 +3,6 @@
 
 require "cask/artifact/moved"
 
-require "extend/hash_validator"
-using HashValidator
-
 module Cask
   module Artifact
     # Generic artifact corresponding to the `artifact` stanza.
diff --git a/Library/Homebrew/cask/artifact/installer.rb b/Library/Homebrew/cask/artifact/installer.rb
index ef20cd0bd1..735a74688f 100644
--- a/Library/Homebrew/cask/artifact/installer.rb
+++ b/Library/Homebrew/cask/artifact/installer.rb
@@ -3,9 +3,6 @@
 
 require "cask/artifact/abstract_artifact"
 
-require "extend/hash_validator"
-using HashValidator
-
 module Cask
   module Artifact
     # Artifact corresponding to the `installer` stanza.
@@ -67,7 +64,7 @@ module Cask
           )
         end
 
-        args.assert_valid_keys!(*VALID_KEYS)
+        args.assert_valid_keys(*VALID_KEYS)
         new(cask, **args)
       end
 
diff --git a/Library/Homebrew/cask/artifact/pkg.rb b/Library/Homebrew/cask/artifact/pkg.rb
index 924f731ae4..7a22057909 100644
--- a/Library/Homebrew/cask/artifact/pkg.rb
+++ b/Library/Homebrew/cask/artifact/pkg.rb
@@ -6,9 +6,6 @@ require "plist"
 require "utils/user"
 require "cask/artifact/abstract_artifact"
 
-require "extend/hash_validator"
-using HashValidator
-
 module Cask
   module Artifact
     # Artifact corresponding to the `pkg` stanza.
@@ -18,7 +15,7 @@ module Cask
       attr_reader :path, :stanza_options
 
       def self.from_args(cask, path, **stanza_options)
-        stanza_options.assert_valid_keys!(:allow_untrusted, :choices)
+        stanza_options.assert_valid_keys(:allow_untrusted, :choices)
         new(cask, path, **stanza_options)
       end
 
diff --git a/Library/Homebrew/cask/artifact/relocated.rb b/Library/Homebrew/cask/artifact/relocated.rb
index ee5ca48d73..80d2e727b1 100644
--- a/Library/Homebrew/cask/artifact/relocated.rb
+++ b/Library/Homebrew/cask/artifact/relocated.rb
@@ -3,9 +3,6 @@
 
 require "cask/artifact/abstract_artifact"
 
-require "extend/hash_validator"
-using HashValidator
-
 module Cask
   module Artifact
     # Superclass for all artifacts which have a source and a target location.
@@ -20,7 +17,7 @@ module Cask
         if target_hash
           raise CaskInvalidError unless target_hash.respond_to?(:keys)
 
-          target_hash.assert_valid_keys!(:target)
+          target_hash.assert_valid_keys(:target)
         end
 
         target_hash ||= {}
diff --git a/Library/Homebrew/cask/cask.rb b/Library/Homebrew/cask/cask.rb
index e654f3260d..5aad041fad 100644
--- a/Library/Homebrew/cask/cask.rb
+++ b/Library/Homebrew/cask/cask.rb
@@ -20,9 +20,6 @@ module Cask
     extend APIHashable
     include Metadata
 
-    # TODO: can be removed when API JSON is regenerated with HOMEBREW_PREFIX_PLACEHOLDER.
-    HOMEBREW_OLD_PREFIX_PLACEHOLDER = "$(brew --prefix)"
-
     attr_reader :token, :sourcefile_path, :source, :config, :default_config, :loader
     attr_accessor :download, :allow_reassignment
 
diff --git a/Library/Homebrew/cask/cask_loader.rb b/Library/Homebrew/cask/cask_loader.rb
index a47a6464a3..7d20ee0af0 100644
--- a/Library/Homebrew/cask/cask_loader.rb
+++ b/Library/Homebrew/cask/cask_loader.rb
@@ -326,13 +326,10 @@ module Cask
       end
 
       def from_h_string_gsubs(string, appdir)
-        # TODO: HOMEBREW_OLD_PREFIX_PLACEHOLDER can be removed when API JSON is
-        #       regenerated with HOMEBREW_PREFIX_PLACEHOLDER.
         string.to_s
               .gsub(HOMEBREW_HOME_PLACEHOLDER, Dir.home)
               .gsub(HOMEBREW_PREFIX_PLACEHOLDER, HOMEBREW_PREFIX)
               .gsub(HOMEBREW_CASK_APPDIR_PLACEHOLDER, appdir)
-              .gsub(Cask::HOMEBREW_OLD_PREFIX_PLACEHOLDER, HOMEBREW_PREFIX)
       end
 
       def from_h_array_gsubs(array, appdir)
diff --git a/Library/Homebrew/cask/cmd.rb b/Library/Homebrew/cask/cmd.rb
index acb6de20e7..127995b692 100644
--- a/Library/Homebrew/cask/cmd.rb
+++ b/Library/Homebrew/cask/cmd.rb
@@ -11,7 +11,6 @@ require "cask/config"
 
 require "cask/cmd/abstract_command"
 require "cask/cmd/audit"
-require "cask/cmd/fetch"
 require "cask/cmd/install"
 require "cask/cmd/reinstall"
 
diff --git a/Library/Homebrew/cask/cmd/fetch.rb b/Library/Homebrew/cask/cmd/fetch.rb
deleted file mode 100644
index da0eb66295..0000000000
--- a/Library/Homebrew/cask/cmd/fetch.rb
+++ /dev/null
@@ -1,41 +0,0 @@
-# typed: false
-# frozen_string_literal: true
-
-module Cask
-  class Cmd
-    # Cask implementation of the `brew fetch` command.
-    #
-    # @api private
-    class Fetch < AbstractCommand
-      extend T::Sig
-
-      def self.parser
-        super do
-          switch "--force",
-                 description: "Force redownloading even if files already exist in local cache."
-        end
-      end
-
-      sig { void }
-      def run
-        require "cask/download"
-        require "cask/installer"
-
-        options = {
-          quarantine: args.quarantine?,
-        }.compact
-
-        options[:quarantine] = true if options[:quarantine].nil?
-
-        casks.each do |cask|
-          puts Installer.caveats(cask)
-          ohai "Downloading external files for Cask #{cask}"
-          download = Download.new(cask, **options)
-          download.clear_cache if args.force?
-          downloaded_path = download.fetch
-          ohai "Success! Downloaded to: #{downloaded_path}"
-        end
-      end
-    end
-  end
-end
diff --git a/Library/Homebrew/cask/cmd/install.rb b/Library/Homebrew/cask/cmd/install.rb
index efd84d9365..c4cbab03ef 100644
--- a/Library/Homebrew/cask/cmd/install.rb
+++ b/Library/Homebrew/cask/cmd/install.rb
@@ -85,8 +85,7 @@ module Cask
 
         if dry_run
           if (casks_to_install = casks.reject(&:installed?).presence)
-            plural = ::Utils.pluralize("cask", casks_to_install.count)
-            ohai "Would install #{casks_to_install.count} #{plural}:"
+            ohai "Would install #{::Utils.pluralize("cask", casks_to_install.count, include_count: true)}:"
             puts casks_to_install.map(&:full_name).join(" ")
           end
           casks.each do |cask|
@@ -97,8 +96,8 @@ module Cask
                                      .map(&:name)
             next if dep_names.blank?
 
-            plural = ::Utils.pluralize("dependenc", dep_names.count, plural: "ies", singular: "y")
-            ohai "Would install #{dep_names.count} #{plural} for #{cask.full_name}:"
+            ohai "Would install #{::Utils.pluralize("dependenc", dep_names.count, plural: "ies", singular: "y",
+                                                    include_count: true)} for #{cask.full_name}:"
             puts dep_names.join(" ")
           end
           return
diff --git a/Library/Homebrew/cask/config.rb b/Library/Homebrew/cask/config.rb
index c99ac319da..ae083bf292 100644
--- a/Library/Homebrew/cask/config.rb
+++ b/Library/Homebrew/cask/config.rb
@@ -6,9 +6,6 @@ require "json"
 require "lazy_object"
 require "locale"
 
-require "extend/hash_validator"
-using HashValidator
-
 module Cask
   # Configuration for installing casks.
   #
@@ -110,8 +107,8 @@ module Cask
         return
       end
 
-      @env&.assert_valid_keys!(*self.class.defaults.keys)
-      @explicit.assert_valid_keys!(*self.class.defaults.keys)
+      @env&.assert_valid_keys(*self.class.defaults.keys)
+      @explicit.assert_valid_keys(*self.class.defaults.keys)
     end
 
     sig { returns(T::Hash[Symbol, T.any(String, Pathname, T::Array[String])]) }
@@ -169,10 +166,12 @@ module Cask
 
     DEFAULT_DIRS.each_key do |dir|
       define_method(dir) do
+        T.bind(self, Config)
         explicit.fetch(dir, env.fetch(dir, default.fetch(dir)))
       end
 
       define_method(:"#{dir}=") do |path|
+        T.bind(self, Config)
         explicit[dir] = Pathname(path).expand_path
       end
     end
diff --git a/Library/Homebrew/cask/dsl.rb b/Library/Homebrew/cask/dsl.rb
index 7976100525..ab5a87f6b3 100644
--- a/Library/Homebrew/cask/dsl.rb
+++ b/Library/Homebrew/cask/dsl.rb
@@ -339,6 +339,7 @@ module Cask
 
     ORDINARY_ARTIFACT_CLASSES.each do |klass|
       define_method(klass.dsl_key) do |*args, **kwargs|
+        T.bind(self, DSL)
         if [*artifacts.map(&:class), klass].include?(Artifact::StageOnly) &&
            (artifacts.map(&:class) & ACTIVATABLE_ARTIFACT_CLASSES).any?
           raise CaskInvalidError.new(cask, "'stage_only' must be the only activatable artifact.")
@@ -355,6 +356,7 @@ module Cask
     ARTIFACT_BLOCK_CLASSES.each do |klass|
       [klass.dsl_key, klass.uninstall_dsl_key].each do |dsl_key|
         define_method(dsl_key) do |&block|
+          T.bind(self, DSL)
           artifacts.add(klass.new(cask, dsl_key => block))
         end
       end
diff --git a/Library/Homebrew/cask/dsl/conflicts_with.rb b/Library/Homebrew/cask/dsl/conflicts_with.rb
index da47113ab5..40b19f6056 100644
--- a/Library/Homebrew/cask/dsl/conflicts_with.rb
+++ b/Library/Homebrew/cask/dsl/conflicts_with.rb
@@ -1,11 +1,8 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "delegate"
 
-require "extend/hash_validator"
-using HashValidator
-
 module Cask
   class DSL
     # Class corresponding to the `conflicts_with` stanza.
@@ -22,16 +19,16 @@ module Cask
       ].freeze
 
       def initialize(**options)
-        options.assert_valid_keys!(*VALID_KEYS)
+        options.assert_valid_keys(*VALID_KEYS)
 
-        conflicts = options.transform_values { |v| Set.new(Array(v)) }
+        conflicts = options.transform_values { |v| Set.new(Kernel.Array(v)) }
         conflicts.default = Set.new
 
         super(conflicts)
       end
 
       def to_json(generator)
-        transform_values(&:to_a).to_json(generator)
+        __getobj__.transform_values(&:to_a).to_json(generator)
       end
     end
   end
diff --git a/Library/Homebrew/cask/dsl/depends_on.rb b/Library/Homebrew/cask/dsl/depends_on.rb
index 48c96b893f..9522f0553e 100644
--- a/Library/Homebrew/cask/dsl/depends_on.rb
+++ b/Library/Homebrew/cask/dsl/depends_on.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "delegate"
@@ -38,7 +38,7 @@ module Cask
         pairs.each do |key, value|
           raise "invalid depends_on key: '#{key.inspect}'" unless VALID_KEYS.include?(key)
 
-          self[key] = send(:"#{key}=", *value)
+          __getobj__[key] = send(:"#{key}=", *value)
         end
       end
 
@@ -54,15 +54,18 @@ module Cask
       def macos=(*args)
         raise "Only a single 'depends_on macos' is allowed." if defined?(@macos)
 
+        # workaround for https://github.com/sorbet/sorbet/issues/6860
+        first_arg = args.first&.to_s
+
         begin
           @macos = if args.count > 1
             MacOSRequirement.new([args], comparator: "==")
           elsif MacOSVersions::SYMBOLS.key?(args.first)
             MacOSRequirement.new([args.first], comparator: "==")
-          elsif /^\s*(?<comparator><|>|[=<>]=)\s*:(?<version>\S+)\s*$/ =~ args.first
-            MacOSRequirement.new([version.to_sym], comparator: comparator)
-          elsif /^\s*(?<comparator><|>|[=<>]=)\s*(?<version>\S+)\s*$/ =~ args.first
-            MacOSRequirement.new([version], comparator: comparator)
+          elsif (md = /^\s*(?<comparator><|>|[=<>]=)\s*:(?<version>\S+)\s*$/.match(first_arg))
+            MacOSRequirement.new([T.must(md[:version]).to_sym], comparator: md[:comparator])
+          elsif (md = /^\s*(?<comparator><|>|[=<>]=)\s*(?<version>\S+)\s*$/.match(first_arg))
+            MacOSRequirement.new([md[:version]], comparator: md[:comparator])
           else # rubocop:disable Lint/DuplicateBranch
             MacOSRequirement.new([args.first], comparator: "==")
           end
diff --git a/Library/Homebrew/cask/dsl/depends_on.rbi b/Library/Homebrew/cask/dsl/depends_on.rbi
new file mode 100644
index 0000000000..92d6827c64
--- /dev/null
+++ b/Library/Homebrew/cask/dsl/depends_on.rbi
@@ -0,0 +1,5 @@
+# typed: strict
+
+class Cask::DSL::DependsOn
+  include Kernel
+end
diff --git a/Library/Homebrew/cask/dsl/version.rb b/Library/Homebrew/cask/dsl/version.rb
index bb02439dbf..2b5170406b 100644
--- a/Library/Homebrew/cask/dsl/version.rb
+++ b/Library/Homebrew/cask/dsl/version.rb
@@ -32,6 +32,7 @@ module Cask
         def define_divider_deletion_method(divider)
           method_name = deletion_method_name(divider)
           define_method(method_name) do
+            T.bind(self, Version)
             version { delete(divider) }
           end
         end
@@ -49,6 +50,7 @@ module Cask
         def define_divider_conversion_method(left_divider, right_divider)
           method_name = conversion_method_name(left_divider, right_divider)
           define_method(method_name) do
+            T.bind(self, Version)
             version { gsub(left_divider, right_divider) }
           end
         end
diff --git a/Library/Homebrew/cask/installer.rb b/Library/Homebrew/cask/installer.rb
index 8f9f756912..e5d7ea2559 100644
--- a/Library/Homebrew/cask/installer.rb
+++ b/Library/Homebrew/cask/installer.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "formula_installer"
@@ -112,8 +112,9 @@ module Cask
 
       install_artifacts
 
-      if @cask.tap&.should_report_analytics?
-        ::Utils::Analytics.report_event(:cask_install, @cask.token, on_request: true)
+      if (tap = @cask.tap) && tap.should_report_analytics?
+        ::Utils::Analytics.report_event(:cask_install, package_name: @cask.token, tap_name: tap.name,
+on_request: true)
       end
 
       purge_backed_up_versioned_files
@@ -241,7 +242,7 @@ module Cask
       save_download_sha if @cask.version.latest?
     rescue => e
       begin
-        already_installed_artifacts.each do |artifact|
+        already_installed_artifacts&.each do |artifact|
           if artifact.respond_to?(:uninstall_phase)
             odebug "Reverting installation of artifact of class #{artifact.class}"
             artifact.uninstall_phase(command: @command, verbose: verbose?, force: force?)
@@ -296,7 +297,7 @@ module Cask
 
       graph = ::Utils::TopologicalHash.graph_package_dependencies(@cask)
 
-      raise CaskSelfReferencingDependencyError, cask.token if graph[@cask].include?(@cask)
+      raise CaskSelfReferencingDependencyError, @cask.token if graph[@cask].include?(@cask)
 
       ::Utils::TopologicalHash.graph_package_dependencies(primary_container.dependencies, graph)
 
@@ -454,7 +455,7 @@ module Cask
       artifacts = @cask.artifacts
 
       odebug "Uninstalling artifacts"
-      odebug "#{artifacts.length} #{::Utils.pluralize("artifact", artifacts.length)} defined", artifacts
+      odebug "#{::Utils.pluralize("artifact", artifacts.length, include_count: true)} defined", artifacts
 
       artifacts.each do |artifact|
         if artifact.respond_to?(:uninstall_phase)
diff --git a/Library/Homebrew/cask/quarantine.rb b/Library/Homebrew/cask/quarantine.rb
index 2b9ec87058..7333b4e231 100644
--- a/Library/Homebrew/cask/quarantine.rb
+++ b/Library/Homebrew/cask/quarantine.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "development_tools"
@@ -11,29 +11,27 @@ module Cask
   module Quarantine
     extend T::Sig
 
-    module_function
-
     QUARANTINE_ATTRIBUTE = "com.apple.quarantine"
 
     QUARANTINE_SCRIPT = (HOMEBREW_LIBRARY_PATH/"cask/utils/quarantine.swift").freeze
 
-    def swift
+    def self.swift
       @swift ||= DevelopmentTools.locate("swift")
     end
-    private :swift
+    private_class_method :swift
 
-    def xattr
+    def self.xattr
       @xattr ||= DevelopmentTools.locate("xattr")
     end
-    private :xattr
+    private_class_method :xattr
 
-    def swift_target_args
+    def self.swift_target_args
       ["-target", "#{Hardware::CPU.arch}-apple-macosx#{MacOS.version}"]
     end
-    private :swift_target_args
+    private_class_method :swift_target_args
 
     sig { returns(Symbol) }
-    def check_quarantine_support
+    def self.check_quarantine_support
       odebug "Checking quarantine support"
 
       if !system_command(xattr, args: ["-h"], print_stderr: false).success?
@@ -58,13 +56,13 @@ module Cask
       end
     end
 
-    def available?
+    def self.available?
       @status ||= check_quarantine_support
 
       @status == :quarantine_available
     end
 
-    def detect(file)
+    def self.detect(file)
       return if file.nil?
 
       odebug "Verifying Gatekeeper status of #{file}"
@@ -76,13 +74,13 @@ module Cask
       quarantine_status
     end
 
-    def status(file)
+    def self.status(file)
       system_command(xattr,
                      args:         ["-p", QUARANTINE_ATTRIBUTE, file],
                      print_stderr: false).stdout.rstrip
     end
 
-    def toggle_no_translocation_bit(attribute)
+    def self.toggle_no_translocation_bit(attribute)
       fields = attribute.split(";")
 
       # Fields: status, epoch, download agent, event ID
@@ -94,7 +92,7 @@ module Cask
       fields.join(";")
     end
 
-    def release!(download_path: nil)
+    def self.release!(download_path: nil)
       return unless detect(download_path)
 
       odebug "Releasing #{download_path} from quarantine"
@@ -112,7 +110,7 @@ module Cask
       raise CaskQuarantineReleaseError.new(download_path, quarantiner.stderr)
     end
 
-    def cask!(cask: nil, download_path: nil, action: true)
+    def self.cask!(cask: nil, download_path: nil, action: true)
       return if cask.nil? || download_path.nil?
 
       return if detect(download_path)
@@ -139,7 +137,7 @@ module Cask
       end
     end
 
-    def propagate(from: nil, to: nil)
+    def self.propagate(from: nil, to: nil)
       return if from.nil? || to.nil?
 
       raise CaskError, "#{from} was not quarantined properly." unless detect(from)
diff --git a/Library/Homebrew/cask/upgrade.rb b/Library/Homebrew/cask/upgrade.rb
index a27925b921..17c38f43be 100644
--- a/Library/Homebrew/cask/upgrade.rb
+++ b/Library/Homebrew/cask/upgrade.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "env_config"
@@ -124,7 +124,9 @@ module Cask
 
       return true if caught_exceptions.empty?
       raise MultipleCaskErrors, caught_exceptions if caught_exceptions.count > 1
-      raise caught_exceptions.first if caught_exceptions.count == 1
+      raise caught_exceptions.fetch(0) if caught_exceptions.count == 1
+
+      false
     end
 
     def self.upgrade_cask(
diff --git a/Library/Homebrew/caveats.rb b/Library/Homebrew/caveats.rb
index 78f607adce..ebd3ff5736 100644
--- a/Library/Homebrew/caveats.rb
+++ b/Library/Homebrew/caveats.rb
@@ -94,7 +94,8 @@ class Caveats
         end
       end
     end
-    s << "\n"
+    s << "\n" unless s.end_with?("\n")
+    s
   end
 
   private
diff --git a/Library/Homebrew/cmd/info.rb b/Library/Homebrew/cmd/info.rb
index 11fd1469cd..0d0580471b 100644
--- a/Library/Homebrew/cmd/info.rb
+++ b/Library/Homebrew/cmd/info.rb
@@ -124,7 +124,7 @@ module Homebrew
     return unless HOMEBREW_CELLAR.exist?
 
     count = Formula.racks.length
-    puts "#{count} #{Utils.pluralize("keg", count)}, #{HOMEBREW_CELLAR.dup.abv}"
+    puts "#{Utils.pluralize("keg", count, include_count: true)}, #{HOMEBREW_CELLAR.dup.abv}"
   end
 
   sig { params(args: CLI::Args).void }
diff --git a/Library/Homebrew/cmd/postgresql-upgrade-database.rb b/Library/Homebrew/cmd/postgresql-upgrade-database.rb
new file mode 100755
index 0000000000..50421460d9
--- /dev/null
+++ b/Library/Homebrew/cmd/postgresql-upgrade-database.rb
@@ -0,0 +1,166 @@
+# typed: false
+# frozen_string_literal: true
+
+require "cli/parser"
+require "formula"
+
+module Homebrew
+  module_function
+
+  sig { returns(CLI::Parser) }
+  def postgresql_upgrade_database_args
+    Homebrew::CLI::Parser.new do
+      description <<~EOS
+        Upgrades the database for the `postgresql` formula.
+      EOS
+
+      named_args :none
+    end
+  end
+
+  sig { void }
+  def postgresql_upgrade_database
+    postgresql_upgrade_database_args.parse
+
+    name = "postgresql"
+    pg = Formula[name]
+    bin = pg.bin
+    var = pg.var
+    version = pg.version
+    pg_version_file = var/"postgres/PG_VERSION"
+
+    pg_version_installed = version.to_s[/^\d+/]
+    pg_version_data = pg_version_file.read.chomp
+    if pg_version_installed == pg_version_data
+      odie <<~EOS
+        #{name} data already upgraded!
+      EOS
+    end
+
+    datadir = var/"postgres"
+    old_datadir = var/"postgres.old"
+    if old_datadir.exist?
+      odie <<~EOS
+        #{old_datadir} already exists!
+        Remove it if you want to upgrade data automatically.
+      EOS
+    end
+
+    old_pg_name = "#{name}@#{pg_version_data}"
+    old_pg_glob = "#{HOMEBREW_CELLAR}/#{old_pg_name}/#{pg_version_data}.*/bin"
+    old_bin = Pathname.glob(old_pg_glob).first
+    old_bin ||= begin
+      Formula[old_pg_name]
+      ohai "brew install #{old_pg_name}"
+      system "brew", "install", old_pg_name
+      Pathname.glob(old_pg_glob).first
+    rescue FormulaUnavailableError
+      nil
+    end
+
+    odie "No #{name} #{pg_version_data}.* version installed!" unless old_bin
+
+    server_stopped = false
+    moved_data = false
+    initdb_run = false
+    upgraded = false
+
+    begin
+      # Following instructions from:
+      # https://www.postgresql.org/docs/10/static/pgupgrade.html
+      ohai "Upgrading #{name} data from #{pg_version_data} to #{pg_version_installed}..."
+      services_json_output = Utils.popen_read("brew", "services", "info", "--all", "--json")
+      services_json = JSON.parse(services_json_output)
+      loaded_service_names = services_json.select { |sj| sj[:loaded] }.map { |sj| sj[:name] }
+      if loaded_service_names.include?(name)
+        system "brew", "services", "stop", name
+        service_stopped = true
+      elsif quiet_system "#{bin}/pg_ctl", "-D", datadir, "status"
+        system "#{bin}/pg_ctl", "-D", datadir, "stop"
+        server_stopped = true
+      end
+
+      # Shut down old server if it is up via brew services
+      system "brew", "services", "stop", old_pg_name if loaded_service_names.include?(old_pg_name)
+
+      # get 'lc_collate' from old DB"
+      unless quiet_system "#{old_bin}/pg_ctl", "-w", "-D", datadir, "status"
+        system "#{old_bin}/pg_ctl", "-w", "-D", datadir, "start"
+      end
+
+      initdb_args = []
+      locale_settings = %w[
+        lc_collate
+        lc_ctype
+        lc_messages
+        lc_monetary
+        lc_numeric
+        lc_time
+        server_encoding
+      ]
+      locale_settings.each do |setting|
+        sql = "SELECT setting FROM pg_settings WHERE name LIKE '#{setting}';"
+        value = Utils.popen_read("#{old_bin}/psql", "postgres", "-qtAX", "-U", ENV.fetch("USER"), "-c", sql).strip
+
+        next if value.empty?
+
+        initdb_args += if setting == "server_encoding"
+          ["-E #{value}"]
+        else
+          ["--#{setting.tr("_", "-")}=#{value}"]
+        end
+      end
+
+      if quiet_system "#{old_bin}/pg_ctl", "-w", "-D", datadir, "status"
+        system "#{old_bin}/pg_ctl", "-w", "-D", datadir, "stop"
+      end
+
+      ohai "Moving #{name} data from #{datadir} to #{old_datadir}..."
+      FileUtils.mv datadir, old_datadir
+      moved_data = true
+
+      (var/"postgres").mkpath
+      ohai "Creating database..."
+      safe_system "#{bin}/initdb", *initdb_args, "#{var}/postgres"
+      initdb_run = true
+
+      ohai "Migrating and upgrading data..."
+      (var/"log").cd do
+        safe_system "#{bin}/pg_upgrade",
+                    "-r",
+                    "-b", old_bin,
+                    "-B", bin,
+                    "-d", old_datadir,
+                    "-D", datadir,
+                    "-j", Hardware::CPU.cores.to_s
+      end
+      upgraded = true
+
+      ohai "Upgraded #{name} data from #{pg_version_data} to #{pg_version_installed}!"
+      ohai "Your #{name} #{pg_version_data} data remains at #{old_datadir}"
+    ensure
+      if upgraded
+        if server_stopped
+          safe_system "#{bin}/pg_ctl", "-D", datadir, "start"
+        elsif service_stopped
+          safe_system "brew", "services", "start", name
+        end
+      else
+        onoe "Upgrading #{name} data from #{pg_version_data} to #{pg_version_installed} failed!"
+        if initdb_run
+          ohai "Removing empty #{name} initdb database..."
+          FileUtils.rm_r datadir
+        end
+        if moved_data
+          ohai "Moving #{name} data back from #{old_datadir} to #{datadir}..."
+          FileUtils.mv old_datadir, datadir
+        end
+        if server_stopped
+          system "#{bin}/pg_ctl", "-D", datadir, "start"
+        elsif service_stopped
+          system "brew", "services", "start", name
+        end
+      end
+    end
+  end
+end
diff --git a/Library/Homebrew/cmd/tap-info.rb b/Library/Homebrew/cmd/tap-info.rb
index 039c861dca..cea6eb2528 100644
--- a/Library/Homebrew/cmd/tap-info.rb
+++ b/Library/Homebrew/cmd/tap-info.rb
@@ -57,10 +57,10 @@ module Homebrew
         command_count += tap.command_files.size
         private_count += 1 if tap.private?
       end
-      info = "#{tap_count} #{Utils.pluralize("tap", tap_count)}"
+      info = Utils.pluralize("tap", tap_count, include_count: true)
       info += ", #{private_count} private"
-      info += ", #{formula_count} #{Utils.pluralize("formula", formula_count, plural: "e")}"
-      info += ", #{command_count} #{Utils.pluralize("command", command_count)}"
+      info += ", #{Utils.pluralize("formula", formula_count, plural: "e", include_count: true)}"
+      info += ", #{Utils.pluralize("command", command_count, include_count: true)}"
       info += ", #{Tap::TAP_DIRECTORY.dup.abv}" if Tap::TAP_DIRECTORY.directory?
       puts info
     else
diff --git a/Library/Homebrew/cmd/update-report.rb b/Library/Homebrew/cmd/update-report.rb
index 3e0df64c35..a31d149cf5 100644
--- a/Library/Homebrew/cmd/update-report.rb
+++ b/Library/Homebrew/cmd/update-report.rb
@@ -233,8 +233,7 @@ module Homebrew
 
     unless updated_taps.empty?
       auto_update_header args: args
-      noun = Utils.pluralize("tap", updated_taps.count)
-      puts "Updated #{updated_taps.count} #{noun} (#{updated_taps.to_sentence})."
+      puts "Updated #{Utils.pluralize("tap", updated_taps.count, include_count: true)} (#{updated_taps.to_sentence})."
       updated = true
     end
 
@@ -656,12 +655,12 @@ class ReporterHub
       output_dump_formula_or_cask_report "Outdated Casks", outdated_casks
     elsif report_all
       if (changed_formulae = select_formula_or_cask(:M).count) && changed_formulae.positive?
-        noun = Utils.pluralize("formula", changed_formulae, plural: "e")
-        ohai "Modified Formulae", "Modified #{changed_formulae} #{noun}."
+        ohai "Modified Formulae",
+             "Modified #{Utils.pluralize("formula", changed_formulae, plural: "e", include_count: true)}."
       end
 
       if (changed_casks = select_formula_or_cask(:MC).count) && changed_casks.positive?
-        ohai "Modified Casks", "Modified #{changed_casks} #{Utils.pluralize("cask", changed_casks)}."
+        ohai "Modified Casks", "Modified #{Utils.pluralize("cask", changed_casks, include_count: true)}."
       end
     else
       outdated_formulae = Formula.installed.select(&:outdated?).map(&:name)
diff --git a/Library/Homebrew/cmd/update-reset.sh b/Library/Homebrew/cmd/update-reset.sh
index a7b597afa5..f87d623b25 100644
--- a/Library/Homebrew/cmd/update-reset.sh
+++ b/Library/Homebrew/cmd/update-reset.sh
@@ -12,6 +12,10 @@ git() {
     # HOMEBREW_LIBRARY is set by bin/brew
     # shellcheck disable=SC2154
     GIT_EXECUTABLE="$("${HOMEBREW_LIBRARY}/Homebrew/shims/shared/git" --homebrew=print-path)"
+    if [[ -z "${GIT_EXECUTABLE}" ]]
+    then
+      odie "Can't find a working Git!"
+    fi
   fi
   "${GIT_EXECUTABLE}" "$@"
 }
diff --git a/Library/Homebrew/cmd/update.sh b/Library/Homebrew/cmd/update.sh
index cf096c46f8..2bcee9996e 100644
--- a/Library/Homebrew/cmd/update.sh
+++ b/Library/Homebrew/cmd/update.sh
@@ -25,6 +25,10 @@ curl() {
   if [[ -z "${CURL_EXECUTABLE}" ]]
   then
     CURL_EXECUTABLE="$("${HOMEBREW_LIBRARY}/Homebrew/shims/shared/curl" --homebrew=print-path)"
+    if [[ -z "${CURL_EXECUTABLE}" ]]
+    then
+      odie "Can't find a working Curl!"
+    fi
   fi
   "${CURL_EXECUTABLE}" "$@"
 }
@@ -33,6 +37,10 @@ git() {
   if [[ -z "${GIT_EXECUTABLE}" ]]
   then
     GIT_EXECUTABLE="$("${HOMEBREW_LIBRARY}/Homebrew/shims/shared/git" --homebrew=print-path)"
+    if [[ -z "${GIT_EXECUTABLE}" ]]
+    then
+      odie "Can't find a working Git!"
+    fi
   fi
   "${GIT_EXECUTABLE}" "$@"
 }
diff --git a/Library/Homebrew/dev-cmd/audit.rb b/Library/Homebrew/dev-cmd/audit.rb
index 15ddc1f72f..407f7ba295 100644
--- a/Library/Homebrew/dev-cmd/audit.rb
+++ b/Library/Homebrew/dev-cmd/audit.rb
@@ -275,22 +275,21 @@ module Homebrew
     if total_problems_count.positive?
       puts new_formula_problem_lines.map { |s| "  #{s}" }
 
-      errors_summary = "#{total_problems_count} #{Utils.pluralize("problem", total_problems_count)}"
+      errors_summary = Utils.pluralize("problem", total_problems_count, include_count: true)
 
       error_sources = []
       if formula_count.positive?
-        error_sources << "#{formula_count} #{Utils.pluralize("formula", formula_count, plural: "e")}"
+        error_sources << Utils.pluralize("formula", formula_count, plural: "e", include_count: true)
       end
-      error_sources << "#{cask_count} #{Utils.pluralize("cask", cask_count)}" if cask_count.positive?
-      error_sources << "#{tap_count} #{Utils.pluralize("tap", tap_count)}" if tap_count.positive?
+      error_sources << Utils.pluralize("cask", cask_count, include_count: true) if cask_count.positive?
+      error_sources << Utils.pluralize("tap", tap_count, include_count: true) if tap_count.positive?
 
       errors_summary += " in #{error_sources.to_sentence}" if error_sources.any?
 
       errors_summary += " detected"
 
       if corrected_problem_count.positive?
-        noun = Utils.pluralize("problem", corrected_problem_count)
-        errors_summary += ", #{corrected_problem_count} #{noun} corrected"
+        errors_summary += ", #{Utils.pluralize("problem", corrected_problem_count, include_count: true)} corrected"
       end
 
       ofail errors_summary
diff --git a/Library/Homebrew/dev-cmd/contributions.rb b/Library/Homebrew/dev-cmd/contributions.rb
index ebad7138c9..3abc22f96e 100755
--- a/Library/Homebrew/dev-cmd/contributions.rb
+++ b/Library/Homebrew/dev-cmd/contributions.rb
@@ -64,7 +64,8 @@ module Homebrew
       results[user] = scan_repositories(repos, user, args)
       grand_totals[user] = total(results[user])
 
-      puts "#{user} contributed #{grand_totals[user].values.sum} times #{time_period(args)}."
+      puts "#{user} contributed #{Utils.pluralize("time", grand_totals[user].values.sum,
+                                                  include_count: true)} #{time_period(args)}."
       puts generate_csv(T.must(user), results[user], grand_totals[user]) if args.csv?
       return
     end
@@ -79,7 +80,8 @@ module Homebrew
       results[username] = scan_repositories(repos, username, args)
       grand_totals[username] = total(results[username])
 
-      puts "#{username} contributed #{grand_totals[username].values.sum} times #{time_period(args)}."
+      puts "#{username} contributed #{Utils.pluralize("time", grand_totals[username].values.sum,
+                                                      include_count: true)} #{time_period(args)}."
     end
 
     puts generate_maintainers_csv(grand_totals) if args.csv?
diff --git a/Library/Homebrew/dev-cmd/pr-pull.rb b/Library/Homebrew/dev-cmd/pr-pull.rb
index 9a1a1618b9..e8ec2195db 100644
--- a/Library/Homebrew/dev-cmd/pr-pull.rb
+++ b/Library/Homebrew/dev-cmd/pr-pull.rb
@@ -22,6 +22,8 @@ module Homebrew
              description: "Download the bottles but don't upload them."
       switch "--no-commit",
              description: "Do not generate a new commit before uploading."
+      switch "--no-cherry-pick",
+             description: "Do not cherry-pick commits from the pull request branch."
       switch "-n", "--dry-run",
              description: "Print what would be done rather than doing it."
       switch "--clean",
@@ -447,10 +449,16 @@ module Homebrew
       ohai "Fetching #{tap} pull request ##{pr}"
       Dir.mktmpdir pr do |dir|
         cd dir do
-          original_commit = ENV["GITHUB_SHA"].presence || tap.path.git_head
+          current_branch_head = ENV["GITHUB_SHA"] || tap.git_head
+          original_commit = if args.no_cherry_pick?
+            # TODO: Handle the case where `merge-base` returns multiple commits.
+            Utils.safe_popen_read("git", "-C", tap.path, "merge-base", "origin/HEAD", current_branch_head).strip
+          else
+            current_branch_head
+          end
 
           unless args.no_commit?
-            cherry_pick_pr!(user, repo, pr, path: tap.path, args: args)
+            cherry_pick_pr!(user, repo, pr, path: tap.path, args: args) unless args.no_cherry_pick?
             if !args.no_autosquash? && !args.dry_run?
               autosquash!(original_commit, tap: tap,
                           verbose: args.verbose?, resolve: args.resolve?, reason: args.message)
diff --git a/Library/Homebrew/diagnostic.rb b/Library/Homebrew/diagnostic.rb
index 39ccbc58fc..9b88e6ef7b 100644
--- a/Library/Homebrew/diagnostic.rb
+++ b/Library/Homebrew/diagnostic.rb
@@ -908,7 +908,7 @@ module Homebrew
               0
             end
 
-            "#{tap.path} (#{cask_count} #{Utils.pluralize("cask", cask_count)})"
+            "#{tap.path} (#{Utils.pluralize("cask", cask_count, include_count: true)})"
           end
         end)
 
diff --git a/Library/Homebrew/download_strategy.rb b/Library/Homebrew/download_strategy.rb
index 0186a3aca8..0074b62ec7 100644
--- a/Library/Homebrew/download_strategy.rb
+++ b/Library/Homebrew/download_strategy.rb
@@ -491,10 +491,13 @@ class CurlDownloadStrategy < AbstractFileDownloadStrategy
         end
       end
 
+      filename = content_disposition.filename if filename.blank?
+      next if filename.blank?
+
       # Servers may include '/' in their Content-Disposition filename header. Take only the basename of this, because:
       # - Unpacking code assumes this is a single file - not something living in a subdirectory.
       # - Directory traversal attacks are possible without limiting this to just the basename.
-      File.basename(filename || content_disposition.filename)
+      File.basename(filename)
     end
 
     filenames = lines.map(&parse_content_disposition).compact
diff --git a/Library/Homebrew/extend/git_repository.rbi b/Library/Homebrew/extend/git_repository.rbi
index 534b936b96..9ffee241cf 100644
--- a/Library/Homebrew/extend/git_repository.rbi
+++ b/Library/Homebrew/extend/git_repository.rbi
@@ -1,8 +1,5 @@
 # typed: strict
 
 module GitRepositoryExtension
-  include Kernel
-
-  sig { params(args: T.any(String, Pathname)).returns(Pathname) }
-  def join(*args); end
+  requires_ancestor { Pathname }
 end
diff --git a/Library/Homebrew/extend/hash_validator.rb b/Library/Homebrew/extend/hash_validator.rb
deleted file mode 100644
index 09cfbe68a3..0000000000
--- a/Library/Homebrew/extend/hash_validator.rb
+++ /dev/null
@@ -1,13 +0,0 @@
-# typed: false
-# frozen_string_literal: true
-
-module HashValidator
-  refine Hash do
-    def assert_valid_keys!(*valid_keys)
-      unknown_keys = keys - valid_keys
-      return if unknown_keys.empty?
-
-      raise ArgumentError, "invalid keys: #{unknown_keys.map(&:inspect).join(", ")}"
-    end
-  end
-end
diff --git a/Library/Homebrew/extend/hash_validator.rbi b/Library/Homebrew/extend/hash_validator.rbi
deleted file mode 100644
index 715b783813..0000000000
--- a/Library/Homebrew/extend/hash_validator.rbi
+++ /dev/null
@@ -1,6 +0,0 @@
-# typed: strict
-
-class Hash
-  sig { params(valid_keys: T.untyped).void }
-  def assert_valid_keys!(*valid_keys); end
-end
diff --git a/Library/Homebrew/extend/kernel.rb b/Library/Homebrew/extend/kernel.rb
index 77c7547376..8c9672ec4a 100644
--- a/Library/Homebrew/extend/kernel.rb
+++ b/Library/Homebrew/extend/kernel.rb
@@ -199,13 +199,13 @@ module Kernel
     if seconds > 59
       minutes = seconds / 60
       seconds %= 60
-      res = +"#{minutes} #{Utils.pluralize("minute", minutes)}"
+      res = +Utils.pluralize("minute", minutes, include_count: true)
       return res.freeze if seconds.zero?
 
       res << " "
     end
 
-    res << "#{seconds} #{Utils.pluralize("second", seconds)}"
+    res << Utils.pluralize("second", seconds, include_count: true)
     res.freeze
   end
 
diff --git a/Library/Homebrew/extend/object.rbi b/Library/Homebrew/extend/object.rbi
new file mode 100644
index 0000000000..cc39405568
--- /dev/null
+++ b/Library/Homebrew/extend/object.rbi
@@ -0,0 +1,6 @@
+# typed: strict
+
+class Object
+  sig { returns(T::Boolean) }
+  def present?; end
+end
diff --git a/Library/Homebrew/extend/on_system.rb b/Library/Homebrew/extend/on_system.rb
index ccd923df4d..5d4c581f44 100644
--- a/Library/Homebrew/extend/on_system.rb
+++ b/Library/Homebrew/extend/on_system.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "simulate_system"
@@ -9,17 +9,15 @@ module OnSystem
   ARCH_OPTIONS = [:intel, :arm].freeze
   BASE_OS_OPTIONS = [:macos, :linux].freeze
 
-  module_function
-
   sig { params(arch: Symbol).returns(T::Boolean) }
-  def arch_condition_met?(arch)
+  def self.arch_condition_met?(arch)
     raise ArgumentError, "Invalid arch condition: #{arch.inspect}" if ARCH_OPTIONS.exclude?(arch)
 
     arch == Homebrew::SimulateSystem.current_arch
   end
 
   sig { params(os_name: Symbol, or_condition: T.nilable(Symbol)).returns(T::Boolean) }
-  def os_condition_met?(os_name, or_condition = nil)
+  def self.os_condition_met?(os_name, or_condition = nil)
     return Homebrew::SimulateSystem.send("simulating_or_running_on_#{os_name}?") if BASE_OS_OPTIONS.include?(os_name)
 
     raise ArgumentError, "Invalid OS condition: #{os_name.inspect}" unless MacOSVersions::SYMBOLS.key?(os_name)
@@ -46,17 +44,17 @@ module OnSystem
   end
 
   sig { params(method_name: Symbol).returns(Symbol) }
-  def condition_from_method_name(method_name)
+  def self.condition_from_method_name(method_name)
     method_name.to_s.sub(/^on_/, "").to_sym
   end
 
   sig { params(base: Class).void }
-  def setup_arch_methods(base)
+  def self.setup_arch_methods(base)
     ARCH_OPTIONS.each do |arch|
       base.define_method("on_#{arch}") do |&block|
         @on_system_blocks_exist = true
 
-        return unless OnSystem.arch_condition_met? OnSystem.condition_from_method_name(__method__)
+        return unless OnSystem.arch_condition_met? OnSystem.condition_from_method_name(T.must(__method__))
 
         @called_in_on_system_block = true
         result = block.call
@@ -75,12 +73,12 @@ module OnSystem
   end
 
   sig { params(base: Class).void }
-  def setup_base_os_methods(base)
+  def self.setup_base_os_methods(base)
     BASE_OS_OPTIONS.each do |base_os|
       base.define_method("on_#{base_os}") do |&block|
         @on_system_blocks_exist = true
 
-        return unless OnSystem.os_condition_met? OnSystem.condition_from_method_name(__method__)
+        return unless OnSystem.os_condition_met? OnSystem.condition_from_method_name(T.must(__method__))
 
         @called_in_on_system_block = true
         result = block.call
@@ -118,12 +116,12 @@ module OnSystem
   end
 
   sig { params(base: Class).void }
-  def setup_macos_methods(base)
+  def self.setup_macos_methods(base)
     MacOSVersions::SYMBOLS.each_key do |os_name|
       base.define_method("on_#{os_name}") do |or_condition = nil, &block|
         @on_system_blocks_exist = true
 
-        os_condition = OnSystem.condition_from_method_name __method__
+        os_condition = OnSystem.condition_from_method_name T.must(__method__)
         return unless OnSystem.os_condition_met? os_condition, or_condition
 
         @called_in_on_system_block = true
diff --git a/Library/Homebrew/extend/os/mac/unpack_strategy/zip.rb b/Library/Homebrew/extend/os/mac/unpack_strategy/zip.rb
index 65585d3cd0..cff64f5802 100644
--- a/Library/Homebrew/extend/os/mac/unpack_strategy/zip.rb
+++ b/Library/Homebrew/extend/os/mac/unpack_strategy/zip.rb
@@ -11,8 +11,6 @@ module UnpackStrategy
       include UnpackStrategy
       include SystemCommand::Mixin
 
-      using Magic
-
       sig { override.params(unpack_dir: Pathname, basename: Pathname, verbose: T::Boolean).returns(T.untyped) }
       def extract_to_dir(unpack_dir, basename:, verbose:)
         with_env(TZ: "UTC") do
diff --git a/Library/Homebrew/extend/os/mac/unpack_strategy/zip.rbi b/Library/Homebrew/extend/os/mac/unpack_strategy/zip.rbi
index ee40416382..43597431d9 100644
--- a/Library/Homebrew/extend/os/mac/unpack_strategy/zip.rbi
+++ b/Library/Homebrew/extend/os/mac/unpack_strategy/zip.rbi
@@ -1,9 +1,5 @@
 # typed: strict
 
-module UnpackStrategy
-  class Zip
-    module MacOSZipExtension
-      include Kernel
-    end
-  end
+module UnpackStrategy::Zip::MacOSZipExtension
+  include Kernel
 end
diff --git a/Library/Homebrew/extend/pathname.rb b/Library/Homebrew/extend/pathname.rb
index a929f153b8..ca9144b27a 100644
--- a/Library/Homebrew/extend/pathname.rb
+++ b/Library/Homebrew/extend/pathname.rb
@@ -343,14 +343,24 @@ class Pathname
     chmod saved_perms if saved_perms
   end
 
+  # @private
+  def which_install_info
+    @which_install_info ||=
+      if File.executable?("/usr/bin/install-info")
+        "/usr/bin/install-info"
+      elsif Formula["texinfo"].any_version_installed?
+        Formula["texinfo"].opt_bin/"install-info"
+      end
+  end
+
   # @private
   def install_info
-    quiet_system "/usr/bin/install-info", "--quiet", to_s, "#{dirname}/dir"
+    quiet_system(which_install_info, "--quiet", to_s, "#{dirname}/dir")
   end
 
   # @private
   def uninstall_info
-    quiet_system "/usr/bin/install-info", "--delete", "--quiet", to_s, "#{dirname}/dir"
+    quiet_system(which_install_info, "--delete", "--quiet", to_s, "#{dirname}/dir")
   end
 
   # Writes an exec script in this folder for each target pathname.
@@ -456,6 +466,32 @@ class Pathname
   def rpaths
     []
   end
+
+  sig { returns(String) }
+  def magic_number
+    @magic_number ||= if directory?
+      ""
+    else
+      # Length of the longest regex (currently Tar).
+      max_magic_number_length = 262
+      # FIXME: The `T.let` is a workaround until we have https://github.com/sorbet/sorbet/pull/6865
+      T.let(binread(max_magic_number_length), T.nilable(String)) || ""
+    end
+  end
+
+  sig { returns(String) }
+  def file_type
+    @file_type ||= system_command("file", args: ["-b", self], print_stderr: false)
+                   .stdout.chomp
+  end
+
+  sig { returns(T::Array[String]) }
+  def zipinfo
+    @zipinfo ||= system_command("zipinfo", args: ["-1", self], print_stderr: false)
+                 .stdout
+                 .encode(Encoding::UTF_8, invalid: :replace)
+                 .split("\n")
+  end
 end
 
 require "extend/os/pathname"
diff --git a/Library/Homebrew/extend/pathname.rbi b/Library/Homebrew/extend/pathname.rbi
index 12a94cd3eb..a682b461ee 100644
--- a/Library/Homebrew/extend/pathname.rbi
+++ b/Library/Homebrew/extend/pathname.rbi
@@ -1,19 +1,9 @@
 # typed: strict
 
 module DiskUsageExtension
-  include Kernel
-
-  def exist?; end
-
-  def symlink?; end
-
-  def resolved_path; end
+  requires_ancestor { Pathname }
 end
 
 module ObserverPathnameExtension
-  include Kernel
-
-  def dirname; end
-
-  def basename; end
+  requires_ancestor { Pathname }
 end
diff --git a/Library/Homebrew/formula_auditor.rb b/Library/Homebrew/formula_auditor.rb
index 40530ef8e1..99aa219f5b 100644
--- a/Library/Homebrew/formula_auditor.rb
+++ b/Library/Homebrew/formula_auditor.rb
@@ -466,6 +466,16 @@ module Homebrew
               "They must not be upgraded to version 7.11 or newer."
     end
 
+    def audit_keg_only_reason
+      return unless @core_tap
+      return unless formula.keg_only?
+
+      keg_only_message = text.to_s.match(/keg_only\s+["'](.*)["']/)&.captures&.first
+      return unless keg_only_message&.include?("HOMEBREW_PREFIX")
+
+      problem "`keg_only` reason should not include `HOMEBREW_PREFIX` as it creates confusing `brew info` output."
+    end
+
     def audit_versioned_keg_only
       return unless @versioned_formula
       return unless @core_tap
diff --git a/Library/Homebrew/formula_installer.rb b/Library/Homebrew/formula_installer.rb
index 12eb8ec499..1cbec1c9ca 100644
--- a/Library/Homebrew/formula_installer.rb
+++ b/Library/Homebrew/formula_installer.rb
@@ -414,9 +414,9 @@ class FormulaInstaller
     options = display_options(formula).join(" ")
     oh1 "Installing #{Formatter.identifier(formula.full_name)} #{options}".strip if show_header?
 
-    if formula.tap&.should_report_analytics?
-      action = "#{formula.full_name} #{options}".strip
-      Utils::Analytics.report_event(:formula_install, action, on_request: installed_on_request?)
+    if (tap = formula.tap) && tap.should_report_analytics?
+      Utils::Analytics.report_event(:formula_install, package_name: formula.name, tap_name: tap.name,
+on_request: installed_on_request?, options: options)
     end
 
     self.class.attempted << formula
diff --git a/Library/Homebrew/install.rb b/Library/Homebrew/install.rb
index 19a09b219e..973f9a1d03 100644
--- a/Library/Homebrew/install.rb
+++ b/Library/Homebrew/install.rb
@@ -326,8 +326,8 @@ module Homebrew
 
       if dry_run
         if (formulae_name_to_install = formulae_to_install.map(&:name))
-          plural = Utils.pluralize("formula", formulae_name_to_install.count, plural: "e")
-          ohai "Would install #{formulae_name_to_install.count} #{plural}:"
+          ohai "Would install #{Utils.pluralize("formula", formulae_name_to_install.count,
+                                                plural: "e", include_count: true)}:"
           puts formulae_name_to_install.join(" ")
 
           formula_installers.each do |fi|
@@ -355,8 +355,8 @@ module Homebrew
     def print_dry_run_dependencies(formula, dependencies, &block)
       return if dependencies.empty?
 
-      plural = Utils.pluralize("dependenc", dependencies.count, plural: "ies", singular: "y")
-      ohai "Would install #{dependencies.count} #{plural} for #{formula.name}:"
+      ohai "Would install #{Utils.pluralize("dependenc", dependencies.count, plural: "ies", singular: "y",
+                                            include_count: true)} for #{formula.name}:"
       formula_names = dependencies.map(&:first).map(&:to_formula).map(&block)
       puts formula_names.join(" ")
     end
diff --git a/Library/Homebrew/keg.rb b/Library/Homebrew/keg.rb
index f878f60f83..8ea2c98f85 100644
--- a/Library/Homebrew/keg.rb
+++ b/Library/Homebrew/keg.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "keg_relocate"
@@ -524,8 +524,8 @@ class Keg
   end
 
   def delete_pyc_files!
-    find { |pn| pn.delete if PYC_EXTENSIONS.include?(pn.extname) }
-    find { |pn| FileUtils.rm_rf pn if pn.basename.to_s == "__pycache__" }
+    path.find { |pn| pn.delete if PYC_EXTENSIONS.include?(pn.extname) }
+    path.find { |pn| FileUtils.rm_rf pn if pn.basename.to_s == "__pycache__" }
   end
 
   def binary_executable_or_library_files
diff --git a/Library/Homebrew/mktemp.rb b/Library/Homebrew/mktemp.rb
index 8e6e9b0883..159c0b88df 100644
--- a/Library/Homebrew/mktemp.rb
+++ b/Library/Homebrew/mktemp.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 # Performs {Formula#mktemp}'s functionality, and tracks the results.
@@ -70,7 +70,7 @@ class Mktemp
     begin
       chown(nil, group_id, @tmpdir)
     rescue Errno::EPERM
-      opoo "Failed setting group \"#{Etc.getgrgid(group_id).name}\" on #{@tmpdir}"
+      opoo "Failed setting group \"#{T.must(Etc.getgrgid(group_id)).name}\" on #{@tmpdir}"
     end
 
     begin
diff --git a/Library/Homebrew/options.rb b/Library/Homebrew/options.rb
index 727a72cfa5..e1877729a0 100644
--- a/Library/Homebrew/options.rb
+++ b/Library/Homebrew/options.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 # A formula option.
diff --git a/Library/Homebrew/options.rbi b/Library/Homebrew/options.rbi
new file mode 100644
index 0000000000..b11d6cd088
--- /dev/null
+++ b/Library/Homebrew/options.rbi
@@ -0,0 +1,8 @@
+# typed: strict
+
+class Options
+  # This is a workaround to enable `alias to_ary to_a`
+  # @see https://github.com/sorbet/sorbet/issues/2378#issuecomment-569474238
+  sig { returns(T::Array[Option]) }
+  def to_a; end
+end
diff --git a/Library/Homebrew/os/linux/elf.rb b/Library/Homebrew/os/linux/elf.rb
index cdfc602fba..ca7d078b89 100644
--- a/Library/Homebrew/os/linux/elf.rb
+++ b/Library/Homebrew/os/linux/elf.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 # {Pathname} extension for dealing with ELF files.
diff --git a/Library/Homebrew/os/linux/elf.rbi b/Library/Homebrew/os/linux/elf.rbi
new file mode 100644
index 0000000000..2c99175895
--- /dev/null
+++ b/Library/Homebrew/os/linux/elf.rbi
@@ -0,0 +1,5 @@
+# typed: strict
+
+module ELFShim
+  requires_ancestor { Pathname }
+end
diff --git a/Library/Homebrew/os/mac/mach.rb b/Library/Homebrew/os/mac/mach.rb
index abadcf8fd6..b421103de7 100644
--- a/Library/Homebrew/os/mac/mach.rb
+++ b/Library/Homebrew/os/mac/mach.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "macho"
diff --git a/Library/Homebrew/os/mac/mach.rbi b/Library/Homebrew/os/mac/mach.rbi
new file mode 100644
index 0000000000..54bb844d78
--- /dev/null
+++ b/Library/Homebrew/os/mac/mach.rbi
@@ -0,0 +1,5 @@
+# typed: strict
+
+module MachOShim
+  include Kernel
+end
diff --git a/Library/Homebrew/os/mac/version.rb b/Library/Homebrew/os/mac/version.rb
index fd709f72f2..d407e882ac 100644
--- a/Library/Homebrew/os/mac/version.rb
+++ b/Library/Homebrew/os/mac/version.rb
@@ -45,7 +45,7 @@ module OS
       sig { returns(T.self_type) }
       def strip_patch
         # Big Sur is 11.x but Catalina is 10.15.x.
-        if major >= 11
+        if T.must(major) >= 11
           self.class.new(major.to_s)
         else
           major_minor
diff --git a/Library/Homebrew/os/mac/version.rbi b/Library/Homebrew/os/mac/version.rbi
deleted file mode 100644
index dc7c90848a..0000000000
--- a/Library/Homebrew/os/mac/version.rbi
+++ /dev/null
@@ -1,10 +0,0 @@
-# typed: strict
-
-module OS
-  module Mac
-    class Version
-      sig { returns(Token) }
-      def major; end
-    end
-  end
-end
diff --git a/Library/Homebrew/rubocops/cask/ast/cask_block.rb b/Library/Homebrew/rubocops/cask/ast/cask_block.rb
index 4f45f6771c..ac0dca7592 100644
--- a/Library/Homebrew/rubocops/cask/ast/cask_block.rb
+++ b/Library/Homebrew/rubocops/cask/ast/cask_block.rb
@@ -36,7 +36,15 @@ module RuboCop
         end
 
         def toplevel_stanzas
-          @toplevel_stanzas ||= stanzas.select(&:toplevel_stanza?)
+          # If a `cask` block only contains one stanza, it is that stanza's direct parent,
+          # otherwise stanzas are grouped in a block and `cask` is that block's parent.
+          is_toplevel_stanza = if cask_body.begin_block?
+            ->(stanza) { stanza.parent_node.parent.cask_block? }
+          else
+            ->(stanza) { stanza.parent_node.cask_block? }
+          end
+
+          @toplevel_stanzas ||= stanzas.select(&is_toplevel_stanza)
         end
 
         def sorted_toplevel_stanzas
diff --git a/Library/Homebrew/rubocops/cask/ast/stanza.rb b/Library/Homebrew/rubocops/cask/ast/stanza.rb
index 2088a43655..88badac8cd 100644
--- a/Library/Homebrew/rubocops/cask/ast/stanza.rb
+++ b/Library/Homebrew/rubocops/cask/ast/stanza.rb
@@ -52,10 +52,6 @@ module RuboCop
           stanza_group == other.stanza_group
         end
 
-        def toplevel_stanza?
-          parent_node.cask_block? || parent_node.parent.cask_block?
-        end
-
         def ==(other)
           self.class == other.class && stanza_node == other.stanza_node
         end
diff --git a/Library/Homebrew/rubocops/cask/extend/node.rb b/Library/Homebrew/rubocops/cask/extend/node.rb
index 20e1e4b7cc..ec79aa4f3f 100644
--- a/Library/Homebrew/rubocops/cask/extend/node.rb
+++ b/Library/Homebrew/rubocops/cask/extend/node.rb
@@ -17,6 +17,8 @@ module RuboCop
       def_node_matcher :cask_block?, "(block (send nil? :cask _) args ...)"
       def_node_matcher :arch_variable?, "(lvasgn _ (send nil? :on_arch_conditional ...))"
 
+      def_node_matcher :begin_block?, "(begin ...)"
+
       def stanza?
         return true if arch_variable?
 
diff --git a/Library/Homebrew/sorbet/rbi/gems/stackprof@0.2.24.rbi b/Library/Homebrew/sorbet/rbi/gems/stackprof@0.2.24.rbi
new file mode 100644
index 0000000000..c60dde1735
--- /dev/null
+++ b/Library/Homebrew/sorbet/rbi/gems/stackprof@0.2.24.rbi
@@ -0,0 +1,88 @@
+# typed: true
+
+# DO NOT EDIT MANUALLY
+# This is an autogenerated file for types exported from the `stackprof` gem.
+# Please instead update this file by running `bin/tapioca gem stackprof`.
+
+module StackProf
+  class << self
+    def results(*_arg0); end
+    def run(*_arg0); end
+    def running?; end
+    def sample; end
+    def start(*_arg0); end
+    def stop; end
+    def use_postponed_job!; end
+  end
+end
+
+class StackProf::Middleware
+  def initialize(app, options = T.unsafe(nil)); end
+
+  def call(env); end
+
+  class << self
+    def enabled; end
+    def enabled=(_arg0); end
+    def enabled?(env); end
+    def interval; end
+    def interval=(_arg0); end
+    def metadata; end
+    def metadata=(_arg0); end
+    def mode; end
+    def mode=(_arg0); end
+    def path; end
+    def path=(_arg0); end
+    def raw; end
+    def raw=(_arg0); end
+    def save; end
+  end
+end
+
+class StackProf::Report
+  def initialize(data); end
+
+  def +(other); end
+  def add_lines(a, b); end
+  def convert_to_d3_flame_graph_format(name, stacks, depth); end
+  def data; end
+  def files; end
+  def flamegraph_row(f, x, y, weight, addr); end
+  def flamegraph_stacks(raw); end
+  def frames(sort_by_total = T.unsafe(nil)); end
+  def max_samples; end
+  def modeline; end
+  def normalized_frames; end
+  def overall_samples; end
+  def print_alphabetical_flamegraph(f = T.unsafe(nil), skip_common = T.unsafe(nil)); end
+  def print_callgrind(f = T.unsafe(nil)); end
+  def print_d3_flamegraph(f = T.unsafe(nil), skip_common = T.unsafe(nil)); end
+  def print_debug; end
+  def print_dump(f = T.unsafe(nil)); end
+  def print_file(filter, f = T.unsafe(nil)); end
+  def print_files(sort_by_total = T.unsafe(nil), limit = T.unsafe(nil), f = T.unsafe(nil)); end
+  def print_flamegraph(f, skip_common, alphabetical = T.unsafe(nil)); end
+  def print_graphviz(options = T.unsafe(nil), f = T.unsafe(nil)); end
+  def print_json(f = T.unsafe(nil)); end
+  def print_method(name, f = T.unsafe(nil)); end
+  def print_stackcollapse; end
+  def print_text(sort_by_total = T.unsafe(nil), limit = T.unsafe(nil), select_files = T.unsafe(nil), reject_files = T.unsafe(nil), select_names = T.unsafe(nil), reject_names = T.unsafe(nil), f = T.unsafe(nil)); end
+  def print_timeline_flamegraph(f = T.unsafe(nil), skip_common = T.unsafe(nil)); end
+  def version; end
+  def walk_method(name); end
+
+  private
+
+  def callers_for(addr); end
+  def root_frames; end
+  def source_display(f, file, lines, range = T.unsafe(nil)); end
+
+  class << self
+    def from_file(file); end
+    def from_json(json); end
+    def parse_json(json); end
+  end
+end
+
+StackProf::Report::MARSHAL_SIGNATURE = T.let(T.unsafe(nil), String)
+StackProf::VERSION = T.let(T.unsafe(nil), String)
diff --git a/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi b/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi
index e3dcef310c..9f9e78ea77 100644
--- a/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi
+++ b/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi
@@ -6469,6 +6469,8 @@ end
 class RuboCop::AST::Node
   def arch_variable?(param0=T.unsafe(nil)); end
 
+  def begin_block?(param0=T.unsafe(nil)); end
+
   def block_args(param0=T.unsafe(nil)); end
 
   def block_body(param0=T.unsafe(nil)); end
diff --git a/Library/Homebrew/sorbet/rbi/todo.rbi b/Library/Homebrew/sorbet/rbi/todo.rbi
index 866476b0d6..73f2bbd607 100644
--- a/Library/Homebrew/sorbet/rbi/todo.rbi
+++ b/Library/Homebrew/sorbet/rbi/todo.rbi
@@ -4,7 +4,6 @@
 
 # typed: false
 
-module ::StackProf; end
 module T::InterfaceWrapper::Helpers; end
 module T::Private::Abstract::Hooks; end
 module T::Private::Methods::MethodHooks; end
diff --git a/Library/Homebrew/sorbet/rbi/upstream.rbi b/Library/Homebrew/sorbet/rbi/upstream.rbi
deleted file mode 100644
index dbade1d0dc..0000000000
--- a/Library/Homebrew/sorbet/rbi/upstream.rbi
+++ /dev/null
@@ -1,23 +0,0 @@
-# typed: strict
-
-# This file contains temporary definitions for fixes that have
-# been submitted upstream to https://github.com/sorbet/sorbet.
-
-class Module
-  # https://github.com/sorbet/sorbet/pull/3732
-  sig do
-    params(
-        arg0: T.any(Symbol, String),
-        arg1: T.any(Proc, Method, UnboundMethod)
-    )
-    .returns(Symbol)
-  end
-  sig do
-    params(
-        arg0: T.any(Symbol, String),
-        blk: T.proc.bind(T.untyped).returns(T.untyped),
-    )
-    .returns(Symbol)
-  end
-  def define_method(arg0, arg1=T.unsafe(nil), &blk); end
-end
diff --git a/Library/Homebrew/system_command.rb b/Library/Homebrew/system_command.rb
index e069a4e27f..af201706d4 100644
--- a/Library/Homebrew/system_command.rb
+++ b/Library/Homebrew/system_command.rb
@@ -7,7 +7,6 @@ require "shellwords"
 
 require "extend/io"
 require "extend/predicable"
-require "extend/hash_validator"
 
 require "extend/time"
 
diff --git a/Library/Homebrew/tap.rb b/Library/Homebrew/tap.rb
index 457fe67726..3439ec0c92 100644
--- a/Library/Homebrew/tap.rb
+++ b/Library/Homebrew/tap.rb
@@ -475,15 +475,15 @@ class Tap
     contents = []
 
     if (command_count = command_files.count).positive?
-      contents << "#{command_count} #{Utils.pluralize("command", command_count)}"
+      contents << Utils.pluralize("command", command_count, include_count: true)
     end
 
     if (cask_count = cask_files.count).positive?
-      contents << "#{cask_count} #{Utils.pluralize("cask", cask_count)}"
+      contents << Utils.pluralize("cask", cask_count, include_count: true)
     end
 
     if (formula_count = formula_files.count).positive?
-      contents << "#{formula_count} #{Utils.pluralize("formula", formula_count, plural: "e")}"
+      contents << Utils.pluralize("formula", formula_count, plural: "e", include_count: true)
     end
 
     contents
diff --git a/Library/Homebrew/test/cask/cmd/fetch_spec.rb b/Library/Homebrew/test/cask/cmd/fetch_spec.rb
deleted file mode 100644
index ad443c43db..0000000000
--- a/Library/Homebrew/test/cask/cmd/fetch_spec.rb
+++ /dev/null
@@ -1,60 +0,0 @@
-# typed: false
-# frozen_string_literal: true
-
-describe Cask::Cmd::Fetch, :cask do
-  let(:local_transmission) do
-    Cask::CaskLoader.load(cask_path("local-transmission"))
-  end
-
-  let(:local_caffeine) do
-    Cask::CaskLoader.load(cask_path("local-caffeine"))
-  end
-
-  it "allows downloading the installer of a Cask" do
-    transmission_location = CurlDownloadStrategy.new(
-      local_transmission.url.to_s, local_transmission.token, local_transmission.version,
-      cache: Cask::Cache.path, **local_transmission.url.specs
-    ).cached_location
-    caffeine_location = CurlDownloadStrategy.new(
-      local_caffeine.url.to_s, local_caffeine.token, local_caffeine.version,
-      cache: Cask::Cache.path, **local_caffeine.url.specs
-    ).cached_location
-
-    expect(transmission_location).not_to exist
-    expect(caffeine_location).not_to exist
-
-    described_class.run("local-transmission", "local-caffeine")
-
-    expect(transmission_location).to exist
-    expect(caffeine_location).to exist
-  end
-
-  it "prevents double fetch (without nuking existing installation)" do
-    cached_location = Cask::Download.new(local_transmission).fetch
-
-    old_ctime = File.stat(cached_location).ctime
-
-    described_class.run("local-transmission", "--no-quarantine")
-    new_ctime = File.stat(cached_location).ctime
-
-    expect(old_ctime.to_i).to eq(new_ctime.to_i)
-  end
-
-  it "allows double fetch with --force" do
-    cached_location = Cask::Download.new(local_transmission).fetch
-
-    old_ctime = File.stat(cached_location).ctime
-    sleep(1)
-
-    described_class.run("local-transmission", "--force", "--no-quarantine")
-    new_ctime = File.stat(cached_location).ctime
-
-    expect(new_ctime.to_i).to be > old_ctime.to_i
-  end
-
-  it "properly handles Casks that are not present" do
-    expect do
-      described_class.run("notacask")
-    end.to raise_error(Cask::CaskUnavailableError)
-  end
-end
diff --git a/Library/Homebrew/test/cask/quarantine_spec.rb b/Library/Homebrew/test/cask/quarantine_spec.rb
index 7ab7b7f2d5..f14d4bd70b 100644
--- a/Library/Homebrew/test/cask/quarantine_spec.rb
+++ b/Library/Homebrew/test/cask/quarantine_spec.rb
@@ -2,7 +2,6 @@
 # frozen_string_literal: true
 
 require "cask/cmd/audit"
-require "cask/cmd/fetch"
 require "cask/cmd/install"
 require "cask/cask_loader"
 require "cask/download"
@@ -29,7 +28,8 @@ describe Cask::Quarantine, :cask do
     end
 
     it "quarantines Cask fetches" do
-      Cask::Cmd::Fetch.run("local-transmission")
+      download = Cask::Download.new(Cask::CaskLoader.load("local-transmission"), quarantine: true)
+      download.fetch
       local_transmission = Cask::CaskLoader.load(cask_path("local-transmission"))
       cached_location = Cask::Download.new(local_transmission).fetch
 
@@ -50,7 +50,8 @@ describe Cask::Quarantine, :cask do
     end
 
     it "quarantines Cask installs even if the fetch was not" do
-      Cask::Cmd::Fetch.run("local-transmission", "--no-quarantine")
+      download = Cask::Download.new(Cask::CaskLoader.load("local-transmission"), quarantine: false)
+      download.fetch
 
       Cask::Cmd::Install.run("local-transmission")
 
@@ -144,7 +145,8 @@ describe Cask::Quarantine, :cask do
     end
 
     it "does not quarantine Cask fetches" do
-      Cask::Cmd::Fetch.run("local-transmission", "--no-quarantine")
+      download = Cask::Download.new(Cask::CaskLoader.load("local-transmission"), quarantine: false)
+      download.fetch
       local_transmission = Cask::CaskLoader.load(cask_path("local-transmission"))
       cached_location = Cask::Download.new(local_transmission).fetch
 
@@ -165,7 +167,8 @@ describe Cask::Quarantine, :cask do
     end
 
     it "does not quarantine Cask installs even if the fetch was" do
-      Cask::Cmd::Fetch.run("local-transmission")
+      download = Cask::Download.new(Cask::CaskLoader.load("local-transmission"), quarantine: true)
+      download.fetch
 
       Cask::Cmd::Install.run("local-transmission", "--no-quarantine")
 
diff --git a/Library/Homebrew/test/caveats_spec.rb b/Library/Homebrew/test/caveats_spec.rb
index fe50877834..e8b394683c 100644
--- a/Library/Homebrew/test/caveats_spec.rb
+++ b/Library/Homebrew/test/caveats_spec.rb
@@ -249,6 +249,32 @@ describe Caveats do
           expect(caveats).to include("#{f.opt_share}/pkgconfig")
         end
       end
+
+      context "when joining different caveat types together" do
+        let(:f) do
+          formula do
+            url "foo-1.0"
+            keg_only "some reason"
+
+            def caveats
+              "something else"
+            end
+
+            service do
+              run [bin/"cmd"]
+            end
+          end
+        end
+
+        let(:caveats) { described_class.new(f).caveats }
+
+        it "adds the correct amount of new lines to the output" do
+          expect(caveats).to include("something else")
+          expect(caveats).to include("keg-only")
+          expect(caveats).to include("if you don't want/need a background service")
+          expect(caveats.count("\n")).to eq(9)
+        end
+      end
     end
 
     describe "shell completions" do
diff --git a/Library/Homebrew/test/utils/analytics_spec.rb b/Library/Homebrew/test/utils/analytics_spec.rb
index c78ccf68a5..93b69a7dd3 100644
--- a/Library/Homebrew/test/utils/analytics_spec.rb
+++ b/Library/Homebrew/test/utils/analytics_spec.rb
@@ -6,7 +6,7 @@ require "formula_installer"
 
 describe Utils::Analytics do
   before do
-    described_class.clear_additional_tags_cache
+    described_class.clear_cache
   end
 
   describe "::label_google" do
@@ -45,64 +45,68 @@ describe Utils::Analytics do
     end
   end
 
-  describe "::additional_tags_influx" do
+  describe "::default_tags_influx" do
     let(:ci) { ", CI" if ENV["CI"] }
 
     it "returns OS_VERSION and prefix when HOMEBREW_PREFIX is a custom prefix on intel" do
       expect(Homebrew).to receive(:default_prefix?).and_return(false).at_least(:once)
-      expect(described_class.additional_tags_influx).to have_key(:prefix)
-      expect(described_class.additional_tags_influx[:prefix]).to eq "custom-prefix"
+      expect(described_class.default_tags_influx).to have_key(:prefix)
+      expect(described_class.default_tags_influx[:prefix]).to eq "custom-prefix"
     end
 
     it "returns OS_VERSION, ARM and prefix when HOMEBREW_PREFIX is a custom prefix on arm" do
       expect(Homebrew).to receive(:default_prefix?).and_return(false).at_least(:once)
-      expect(described_class.additional_tags_influx).to have_key(:arch)
-      expect(described_class.additional_tags_influx[:arch]).to eq HOMEBREW_PHYSICAL_PROCESSOR
-      expect(described_class.additional_tags_influx).to have_key(:prefix)
-      expect(described_class.additional_tags_influx[:prefix]).to eq "custom-prefix"
+      expect(described_class.default_tags_influx).to have_key(:arch)
+      expect(described_class.default_tags_influx[:arch]).to eq HOMEBREW_PHYSICAL_PROCESSOR
+      expect(described_class.default_tags_influx).to have_key(:prefix)
+      expect(described_class.default_tags_influx[:prefix]).to eq "custom-prefix"
     end
 
     it "returns OS_VERSION, Rosetta and prefix when HOMEBREW_PREFIX is a custom prefix on Rosetta", :needs_macos do
       expect(Homebrew).to receive(:default_prefix?).and_return(false).at_least(:once)
-      expect(described_class.additional_tags_influx).to have_key(:prefix)
-      expect(described_class.additional_tags_influx[:prefix]).to eq "custom-prefix"
+      expect(described_class.default_tags_influx).to have_key(:prefix)
+      expect(described_class.default_tags_influx[:prefix]).to eq "custom-prefix"
     end
 
     it "does not include prefix when HOMEBREW_PREFIX is the default prefix" do
       expect(Homebrew).to receive(:default_prefix?).and_return(true).at_least(:once)
-      expect(described_class.additional_tags_influx).to have_key(:prefix)
-      expect(described_class.additional_tags_influx[:prefix]).to eq HOMEBREW_PREFIX.to_s
+      expect(described_class.default_tags_influx).to have_key(:prefix)
+      expect(described_class.default_tags_influx[:prefix]).to eq HOMEBREW_PREFIX.to_s
     end
 
     it "includes CI when ENV['CI'] is set" do
       ENV["CI"] = "1"
-      expect(described_class.additional_tags_influx).to have_key(:ci)
+      expect(described_class.default_tags_influx).to have_key(:ci)
     end
 
     it "includes developer when ENV['HOMEBREW_DEVELOPER'] is set" do
       expect(Homebrew::EnvConfig).to receive(:developer?).and_return(true)
-      expect(described_class.additional_tags_influx).to have_key(:developer)
+      expect(described_class.default_tags_influx).to have_key(:developer)
     end
   end
 
   describe "::report_event" do
     let(:f) { formula { url "foo-1.0" } }
-    let(:options) { ["--head"].join }
-    let(:action)  { "#{f.full_name} #{options}".strip }
+    let(:package_name)  { f.name }
+    let(:tap_name) { f.tap.name }
+    let(:on_request) { false }
+    let(:options) { "--HEAD" }
 
     context "when ENV vars is set" do
       it "returns nil when HOMEBREW_NO_ANALYTICS is true" do
         ENV["HOMEBREW_NO_ANALYTICS"] = "true"
         expect(described_class).not_to receive(:report_google)
         expect(described_class).not_to receive(:report_influx)
-        described_class.report_event(:install, action)
+        described_class.report_event(:install, package_name: package_name, tap_name: tap_name,
+          on_request: on_request, options: options)
       end
 
       it "returns nil when HOMEBREW_NO_ANALYTICS_THIS_RUN is true" do
         ENV["HOMEBREW_NO_ANALYTICS_THIS_RUN"] = "true"
         expect(described_class).not_to receive(:report_google)
         expect(described_class).not_to receive(:report_influx)
-        described_class.report_event(:install, action)
+        described_class.report_event(:install, package_name: package_name, tap_name: tap_name,
+          on_request: on_request, options: options)
       end
 
       it "returns nil when HOMEBREW_ANALYTICS_DEBUG is true" do
@@ -112,7 +116,8 @@ describe Utils::Analytics do
         expect(described_class).to receive(:report_google)
         expect(described_class).to receive(:report_influx)
 
-        described_class.report_event(:install, action)
+        described_class.report_event(:install, package_name: package_name, tap_name: tap_name,
+          on_request: on_request, options: options)
       end
     end
 
@@ -120,40 +125,47 @@ describe Utils::Analytics do
       ENV.delete("HOMEBREW_NO_ANALYTICS_THIS_RUN")
       ENV.delete("HOMEBREW_NO_ANALYTICS")
       ENV["HOMEBREW_ANALYTICS_DEBUG"] = "true"
-      expect(Homebrew::EnvConfig).to receive(:developer?).and_return(false)
-      expect(described_class).to receive(:report_google).with(:event, hash_including(ea: action)).once
-      expect(described_class).to receive(:report_influx).with(:install, "formula_name --head", false,
-                                                              hash_including(developer: false)).once
-      described_class.report_event(:install, action)
+      expect(described_class).to receive(:report_google).with(:event,
+                                                              hash_including(ea: "#{package_name} #{options}")).once
+      expect(described_class).to receive(:report_influx).with(:install, hash_including(package_name: package_name,
+                                                                                       on_request:   on_request)).once
+      described_class.report_event(:install, package_name: package_name, tap_name: tap_name,
+          on_request: on_request, options: options)
     end
 
     it "sends to google twice on request" do
       ENV.delete("HOMEBREW_NO_ANALYTICS_THIS_RUN")
       ENV.delete("HOMEBREW_NO_ANALYTICS")
       ENV["HOMEBREW_ANALYTICS_DEBUG"] = "true"
-      expect(Homebrew::EnvConfig).to receive(:developer?).and_return(false)
-      expect(described_class).to receive(:report_google).with(:event, hash_including(ea: action, ec: :install)).once
       expect(described_class).to receive(:report_google).with(:event,
-                                                              hash_including(ea: action,
+                                                              hash_including(ea: "#{package_name} #{options}",
+                                                                             ec: :install)).once
+      expect(described_class).to receive(:report_google).with(:event,
+                                                              hash_including(ea: "#{package_name} #{options}",
                                                                              ec: :install_on_request)).once
-      expect(described_class).to receive(:report_influx).with(:install, "formula_name --head", true,
-                                                              hash_including(developer: false)).once
+      expect(described_class).to receive(:report_influx).with(:install,
+                                                              hash_including(package_name: package_name,
+                                                                             on_request:   true)).once
 
-      described_class.report_event(:install, action, on_request: true)
+      described_class.report_event(:install, package_name: package_name, tap_name: tap_name,
+          on_request: true, options: options)
     end
   end
 
   describe "::report_influx" do
     let(:f) { formula { url "foo-1.0" } }
-    let(:options) { ["--head"].join }
-    let(:action)  { "#{f.full_name} #{options}".strip }
+    let(:package_name)  { f.name }
+    let(:tap_name) { f.tap.name }
+    let(:on_request) { false }
+    let(:options) { "--HEAD" }
 
     it "outputs in debug mode" do
       ENV.delete("HOMEBREW_NO_ANALYTICS_THIS_RUN")
       ENV.delete("HOMEBREW_NO_ANALYTICS")
       ENV["HOMEBREW_ANALYTICS_DEBUG"] = "true"
       expect(described_class).to receive(:deferred_curl).once
-      described_class.report_influx(:install, action, true, developer: true, CI: true)
+      described_class.report_influx(:install, package_name: package_name, tap_name: tap_name, on_request: on_request,
+options: options)
     end
   end
 
diff --git a/Library/Homebrew/test/utils_spec.rb b/Library/Homebrew/test/utils_spec.rb
index 8b9b5e89e8..744014ad94 100644
--- a/Library/Homebrew/test/utils_spec.rb
+++ b/Library/Homebrew/test/utils_spec.rb
@@ -70,6 +70,12 @@ describe Utils do
       expect(described_class.pluralize("foo", 1, singular: "o", plural: "es")).to eq("fooo")
       expect(described_class.pluralize("foo", 2, singular: "o", plural: "es")).to eq("fooes")
     end
+
+    it "includes the count when requested" do
+      expect(described_class.pluralize("foo", 0, include_count: true)).to eq("0 foos")
+      expect(described_class.pluralize("foo", 1, include_count: true)).to eq("1 foo")
+      expect(described_class.pluralize("foo", 2, include_count: true)).to eq("2 foos")
+    end
   end
 
   describe ".underscore" do
diff --git a/Library/Homebrew/unpack_strategy.rb b/Library/Homebrew/unpack_strategy.rb
index b7572d18e7..8a29604b93 100644
--- a/Library/Homebrew/unpack_strategy.rb
+++ b/Library/Homebrew/unpack_strategy.rb
@@ -1,29 +1,8 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "system_command"
 
-# Helper module for iterating over directory trees.
-#
-# @api private
-module PathnameEachDirectory
-  refine Pathname do
-    extend T::Sig
-
-    sig {
-      type_parameters(:T)
-        .params(
-          _block: T.proc.params(path: Pathname).returns(T.type_parameter(:T)),
-        ).returns(T.type_parameter(:T))
-    }
-    def each_directory(&_block)
-      find do |path|
-        yield path if path.directory?
-      end
-    end
-  end
-end
-
 # Module containing all available strategies for unpacking archives.
 #
 # @api private
@@ -33,38 +12,6 @@ module UnpackStrategy
 
   include SystemCommand::Mixin
 
-  using PathnameEachDirectory
-
-  # Helper module for identifying the file type.
-  module Magic
-    # Length of the longest regex (currently Tar).
-    MAX_MAGIC_NUMBER_LENGTH = 262
-    private_constant :MAX_MAGIC_NUMBER_LENGTH
-
-    refine Pathname do
-      def magic_number
-        @magic_number ||= if directory?
-          ""
-        else
-          binread(MAX_MAGIC_NUMBER_LENGTH) || ""
-        end
-      end
-
-      def file_type
-        @file_type ||= system_command("file", args: ["-b", self], print_stderr: false)
-                       .stdout.chomp
-      end
-
-      def zipinfo
-        @zipinfo ||= system_command("zipinfo", args: ["-1", self], print_stderr: false)
-                     .stdout
-                     .encode(Encoding::UTF_8, invalid: :replace)
-                     .split("\n")
-      end
-    end
-  end
-  private_constant :Magic
-
   def self.strategies
     @strategies ||= [
       Tar, # Needs to be before Bzip2/Gzip/Xz/Lzma/Zstd.
@@ -195,7 +142,7 @@ module UnpackStrategy
       end
 
       # Ensure all extracted directories are writable.
-      tmp_unpack_dir.each_directory do |path|
+      each_directory(tmp_unpack_dir) do |path|
         next if path.writable?
 
         FileUtils.chmod "u+w", path, verbose: verbose
@@ -208,6 +155,19 @@ module UnpackStrategy
   def dependencies
     []
   end
+
+  # Helper method for iterating over directory trees.
+  sig {
+    params(
+      pathname: Pathname,
+      _block:   T.proc.params(path: Pathname).void,
+    ).returns(T.nilable(Pathname))
+  }
+  def each_directory(pathname, &_block)
+    pathname.find do |path|
+      yield path if path.directory?
+    end
+  end
 end
 
 require "unpack_strategy/air"
diff --git a/Library/Homebrew/unpack_strategy.rbi b/Library/Homebrew/unpack_strategy.rbi
index 55284f6668..d7550c56b2 100644
--- a/Library/Homebrew/unpack_strategy.rbi
+++ b/Library/Homebrew/unpack_strategy.rbi
@@ -3,14 +3,3 @@
 module UnpackStrategy
   include Kernel
 end
-
-class Pathname
-  sig { returns(String) }
-  def magic_number; end
-
-  sig { returns(String) }
-  def file_type; end
-
-  sig { returns(T::Array[String]) }
-  def zipinfo; end
-end
diff --git a/Library/Homebrew/unpack_strategy/air.rb b/Library/Homebrew/unpack_strategy/air.rb
index 9f8bd8c473..aac0881fa8 100644
--- a/Library/Homebrew/unpack_strategy/air.rb
+++ b/Library/Homebrew/unpack_strategy/air.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
 
     include UnpackStrategy
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".air"]
diff --git a/Library/Homebrew/unpack_strategy/bazaar.rb b/Library/Homebrew/unpack_strategy/bazaar.rb
index 12fbd503d0..62eb0c4946 100644
--- a/Library/Homebrew/unpack_strategy/bazaar.rb
+++ b/Library/Homebrew/unpack_strategy/bazaar.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
   class Bazaar < Directory
     extend T::Sig
 
-    using Magic
-
     def self.can_extract?(path)
       super && (path/".bzr").directory?
     end
diff --git a/Library/Homebrew/unpack_strategy/bzip2.rb b/Library/Homebrew/unpack_strategy/bzip2.rb
index 6b05e4dc15..82e9501b6a 100644
--- a/Library/Homebrew/unpack_strategy/bzip2.rb
+++ b/Library/Homebrew/unpack_strategy/bzip2.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
 
     include UnpackStrategy
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".bz2"]
diff --git a/Library/Homebrew/unpack_strategy/cab.rb b/Library/Homebrew/unpack_strategy/cab.rb
index 82265231d5..de2258af88 100644
--- a/Library/Homebrew/unpack_strategy/cab.rb
+++ b/Library/Homebrew/unpack_strategy/cab.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
 
     include UnpackStrategy
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".cab"]
diff --git a/Library/Homebrew/unpack_strategy/compress.rb b/Library/Homebrew/unpack_strategy/compress.rb
index 65f9ea8728..0cc11abbd7 100644
--- a/Library/Homebrew/unpack_strategy/compress.rb
+++ b/Library/Homebrew/unpack_strategy/compress.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
   class Compress < Tar
     extend T::Sig
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".Z"]
diff --git a/Library/Homebrew/unpack_strategy/cvs.rb b/Library/Homebrew/unpack_strategy/cvs.rb
index 66c2f17f8f..af6f0a3a77 100644
--- a/Library/Homebrew/unpack_strategy/cvs.rb
+++ b/Library/Homebrew/unpack_strategy/cvs.rb
@@ -6,8 +6,6 @@ require_relative "directory"
 module UnpackStrategy
   # Strategy for unpacking CVS repositories.
   class Cvs < Directory
-    using Magic
-
     def self.can_extract?(path)
       super && (path/"CVS").directory?
     end
diff --git a/Library/Homebrew/unpack_strategy/directory.rb b/Library/Homebrew/unpack_strategy/directory.rb
index 02772dcc68..f20b9a566e 100644
--- a/Library/Homebrew/unpack_strategy/directory.rb
+++ b/Library/Homebrew/unpack_strategy/directory.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
 
     include UnpackStrategy
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       []
diff --git a/Library/Homebrew/unpack_strategy/dmg.rb b/Library/Homebrew/unpack_strategy/dmg.rb
index ffc13ae44f..cb3ee47d12 100644
--- a/Library/Homebrew/unpack_strategy/dmg.rb
+++ b/Library/Homebrew/unpack_strategy/dmg.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "tempfile"
@@ -12,6 +12,8 @@ module UnpackStrategy
 
     # Helper module for listing the contents of a volume mounted from a disk image.
     module Bom
+      extend T::Sig
+
       DMG_METADATA = Set.new(%w[
         .background
         .com.apple.timemachine.donotpresent
@@ -35,117 +37,107 @@ module UnpackStrategy
         end
       end
 
-      refine Pathname do
-        extend T::Sig
+      # Check if path is considered disk image metadata.
+      sig { params(pathname: Pathname).returns(T::Boolean) }
+      def self.dmg_metadata?(pathname)
+        DMG_METADATA.include?(pathname.cleanpath.ascend.to_a.last.to_s)
+      end
 
-        # Check if path is considered disk image metadata.
-        sig { returns(T::Boolean) }
-        def dmg_metadata?
-          DMG_METADATA.include?(cleanpath.ascend.to_a.last.to_s)
+      # Check if path is a symlink to a system directory (commonly to /Applications).
+      sig { params(pathname: Pathname).returns(T::Boolean) }
+      def self.system_dir_symlink?(pathname)
+        pathname.symlink? && MacOS.system_dir?(pathname.dirname.join(pathname.readlink))
+      end
+
+      sig { params(pathname: Pathname).returns(String) }
+      def self.bom(pathname)
+        tries = 0
+        result = loop do
+          # We need to use `find` here instead of Ruby in order to properly handle
+          # file names containing special characters, such as “e” + “´” vs. “é”.
+          r = system_command("find", args: [".", "-print0"], chdir: pathname, print_stderr: false)
+          tries += 1
+
+          # Spurious bug on CI, which in most cases can be worked around by retrying.
+          break r unless r.stderr.match?(/Interrupted system call/i)
+
+          raise "Command `#{r.command.shelljoin}` was interrupted." if tries >= 3
         end
 
-        # Check if path is a symlink to a system directory (commonly to /Applications).
-        sig { returns(T::Boolean) }
-        def system_dir_symlink?
-          symlink? && MacOS.system_dir?(dirname.join(readlink))
-        end
+        odebug "Command `#{result.command.shelljoin}` in '#{pathname}' took #{tries} tries." if tries > 1
 
-        sig { returns(String) }
-        def bom
-          tries = 0
-          result = loop do
-            # We need to use `find` here instead of Ruby in order to properly handle
-            # file names containing special characters, such as “e” + “´” vs. “é”.
-            r = system_command("find", args: [".", "-print0"], chdir: self, print_stderr: false)
-            tries += 1
+        bom_paths = result.stdout.split("\0")
 
-            # Spurious bug on CI, which in most cases can be worked around by retrying.
-            break r unless r.stderr.match?(/Interrupted system call/i)
+        raise EmptyError, pathname if bom_paths.empty?
 
-            raise "Command `#{r.command.shelljoin}` was interrupted." if tries >= 3
-          end
-
-          odebug "Command `#{result.command.shelljoin}` in '#{self}' took #{tries} tries." if tries > 1
-
-          bom_paths = result.stdout.split("\0")
-
-          raise EmptyError, self if bom_paths.empty?
-
-          bom_paths
-            .reject { |path| Pathname(path).dmg_metadata? }
-            .reject { |path| (self/path).system_dir_symlink? }
-            .join("\n")
-        end
+        bom_paths
+          .reject { |path| dmg_metadata?(Pathname(path)) }
+          .reject { |path| system_dir_symlink?(pathname/path) }
+          .join("\n")
       end
     end
-    private_constant :Bom
 
     # Strategy for unpacking a volume mounted from a disk image.
     class Mount
       extend T::Sig
 
-      using Bom
       include UnpackStrategy
 
       def eject(verbose: false)
-        tries ||= 3
+        tries = 3
+        begin
+          return unless path.exist?
 
-        return unless path.exist?
+          if tries > 1
+            disk_info = system_command!(
+              "diskutil",
+              args:         ["info", "-plist", path],
+              print_stderr: false,
+              verbose:      verbose,
+            )
 
-        if tries > 1
-          disk_info = system_command!(
-            "diskutil",
-            args:         ["info", "-plist", path],
-            print_stderr: false,
-            verbose:      verbose,
-          )
+            # For HFS, just use <mount-path>
+            # For APFS, find the <physical-store> corresponding to <mount-path>
+            eject_paths = disk_info.plist
+                                   .fetch("APFSPhysicalStores", [])
+                                   .map { |store| store["APFSPhysicalStore"] }
+                                   .compact
+                                   .presence || [path]
 
-          # For HFS, just use <mount-path>
-          # For APFS, find the <physical-store> corresponding to <mount-path>
-          eject_paths = disk_info.plist
-                                 .fetch("APFSPhysicalStores", [])
-                                 .map { |store| store["APFSPhysicalStore"] }
-                                 .compact
-                                 .presence || [path]
-
-          eject_paths.each do |eject_path|
+            eject_paths.each do |eject_path|
+              system_command! "diskutil",
+                              args:         ["eject", eject_path],
+                              print_stderr: false,
+                              verbose:      verbose
+            end
+          else
             system_command! "diskutil",
-                            args:         ["eject", eject_path],
+                            args:         ["unmount", "force", path],
                             print_stderr: false,
                             verbose:      verbose
           end
-        else
-          system_command! "diskutil",
-                          args:         ["unmount", "force", path],
-                          print_stderr: false,
-                          verbose:      verbose
-        end
-      rescue ErrorDuringExecution => e
-        raise e if (tries -= 1).zero?
+        rescue ErrorDuringExecution => e
+          raise e if (tries -= 1).zero?
 
-        sleep 1
-        retry
+          sleep 1
+          retry
+        end
       end
 
       private
 
       sig { override.params(unpack_dir: Pathname, basename: Pathname, verbose: T::Boolean).returns(T.untyped) }
       def extract_to_dir(unpack_dir, basename:, verbose:)
+        tries = 3
         bom = begin
-          tries ||= 10
-
-          path.bom
+          Bom.bom(path)
         rescue Bom::EmptyError => e
-          raise "#{e} No retries left." if (tries -= 1).zero?
+          raise e if (tries -= 1).zero?
 
           sleep 1
           retry
         end
 
-        # TODO: Remove this if we actually ever hit this, i.e. if we actually found
-        #       some files after waiting longer for the DMG to be mounted.
-        raise "BOM for path '#{path}' was empty but retrying for #{10 - tries} seconds helped." if tries != 10
-
         Tempfile.open(["", ".bom"]) do |bomfile|
           bomfile.close
 
diff --git a/Library/Homebrew/unpack_strategy/executable.rb b/Library/Homebrew/unpack_strategy/executable.rb
index 1daeb7d0f7..6bf45599ed 100644
--- a/Library/Homebrew/unpack_strategy/executable.rb
+++ b/Library/Homebrew/unpack_strategy/executable.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
   class Executable < Uncompressed
     extend T::Sig
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".sh", ".bash"]
diff --git a/Library/Homebrew/unpack_strategy/fossil.rb b/Library/Homebrew/unpack_strategy/fossil.rb
index ddaf147795..a09218cf77 100644
--- a/Library/Homebrew/unpack_strategy/fossil.rb
+++ b/Library/Homebrew/unpack_strategy/fossil.rb
@@ -11,8 +11,6 @@ module UnpackStrategy
     include UnpackStrategy
     extend SystemCommand::Mixin
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       []
diff --git a/Library/Homebrew/unpack_strategy/generic_unar.rb b/Library/Homebrew/unpack_strategy/generic_unar.rb
index 0322d5c9ef..a860f8ec6b 100644
--- a/Library/Homebrew/unpack_strategy/generic_unar.rb
+++ b/Library/Homebrew/unpack_strategy/generic_unar.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
 
     include UnpackStrategy
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       []
diff --git a/Library/Homebrew/unpack_strategy/git.rb b/Library/Homebrew/unpack_strategy/git.rb
index 23257c0502..ab39f3c4e0 100644
--- a/Library/Homebrew/unpack_strategy/git.rb
+++ b/Library/Homebrew/unpack_strategy/git.rb
@@ -6,8 +6,6 @@ require_relative "directory"
 module UnpackStrategy
   # Strategy for unpacking Git repositories.
   class Git < Directory
-    using Magic
-
     def self.can_extract?(path)
       super && (path/".git").directory?
     end
diff --git a/Library/Homebrew/unpack_strategy/gzip.rb b/Library/Homebrew/unpack_strategy/gzip.rb
index 983d995a98..dbc70d2766 100644
--- a/Library/Homebrew/unpack_strategy/gzip.rb
+++ b/Library/Homebrew/unpack_strategy/gzip.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
 
     include UnpackStrategy
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".gz"]
diff --git a/Library/Homebrew/unpack_strategy/jar.rb b/Library/Homebrew/unpack_strategy/jar.rb
index d4170a8689..21153d1c2b 100644
--- a/Library/Homebrew/unpack_strategy/jar.rb
+++ b/Library/Homebrew/unpack_strategy/jar.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
   class Jar < Uncompressed
     extend T::Sig
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".apk", ".jar"]
diff --git a/Library/Homebrew/unpack_strategy/lha.rb b/Library/Homebrew/unpack_strategy/lha.rb
index 543f4e4540..a8cdfdb4cf 100644
--- a/Library/Homebrew/unpack_strategy/lha.rb
+++ b/Library/Homebrew/unpack_strategy/lha.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
 
     include UnpackStrategy
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".lha", ".lzh"]
diff --git a/Library/Homebrew/unpack_strategy/lua_rock.rb b/Library/Homebrew/unpack_strategy/lua_rock.rb
index 6150e2788e..d5ce7de33e 100644
--- a/Library/Homebrew/unpack_strategy/lua_rock.rb
+++ b/Library/Homebrew/unpack_strategy/lua_rock.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
   class LuaRock < Uncompressed
     extend T::Sig
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".rock"]
diff --git a/Library/Homebrew/unpack_strategy/lzip.rb b/Library/Homebrew/unpack_strategy/lzip.rb
index da8a991b9e..d1f2c432af 100644
--- a/Library/Homebrew/unpack_strategy/lzip.rb
+++ b/Library/Homebrew/unpack_strategy/lzip.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
 
     include UnpackStrategy
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".lz"]
diff --git a/Library/Homebrew/unpack_strategy/lzma.rb b/Library/Homebrew/unpack_strategy/lzma.rb
index 7ef147b61b..bfe04be2c9 100644
--- a/Library/Homebrew/unpack_strategy/lzma.rb
+++ b/Library/Homebrew/unpack_strategy/lzma.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
 
     include UnpackStrategy
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".lzma"]
diff --git a/Library/Homebrew/unpack_strategy/mercurial.rb b/Library/Homebrew/unpack_strategy/mercurial.rb
index cc27a11395..72d9547933 100644
--- a/Library/Homebrew/unpack_strategy/mercurial.rb
+++ b/Library/Homebrew/unpack_strategy/mercurial.rb
@@ -6,8 +6,6 @@ require_relative "directory"
 module UnpackStrategy
   # Strategy for unpacking Mercurial repositories.
   class Mercurial < Directory
-    using Magic
-
     def self.can_extract?(path)
       super && (path/".hg").directory?
     end
diff --git a/Library/Homebrew/unpack_strategy/microsoft_office_xml.rb b/Library/Homebrew/unpack_strategy/microsoft_office_xml.rb
index 616d78bc06..ad3940d86e 100644
--- a/Library/Homebrew/unpack_strategy/microsoft_office_xml.rb
+++ b/Library/Homebrew/unpack_strategy/microsoft_office_xml.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
   class MicrosoftOfficeXml < Uncompressed
     extend T::Sig
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [
diff --git a/Library/Homebrew/unpack_strategy/otf.rb b/Library/Homebrew/unpack_strategy/otf.rb
index e94eb15029..61ac40a249 100644
--- a/Library/Homebrew/unpack_strategy/otf.rb
+++ b/Library/Homebrew/unpack_strategy/otf.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
   class Otf < Uncompressed
     extend T::Sig
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".otf"]
diff --git a/Library/Homebrew/unpack_strategy/p7zip.rb b/Library/Homebrew/unpack_strategy/p7zip.rb
index 618ea06f23..715c816076 100644
--- a/Library/Homebrew/unpack_strategy/p7zip.rb
+++ b/Library/Homebrew/unpack_strategy/p7zip.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
 
     include UnpackStrategy
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".7z"]
diff --git a/Library/Homebrew/unpack_strategy/pax.rb b/Library/Homebrew/unpack_strategy/pax.rb
index 4067132c80..c454b57ab4 100644
--- a/Library/Homebrew/unpack_strategy/pax.rb
+++ b/Library/Homebrew/unpack_strategy/pax.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
 
     include UnpackStrategy
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".pax"]
diff --git a/Library/Homebrew/unpack_strategy/pkg.rb b/Library/Homebrew/unpack_strategy/pkg.rb
index 220b86a58c..7151ba6078 100644
--- a/Library/Homebrew/unpack_strategy/pkg.rb
+++ b/Library/Homebrew/unpack_strategy/pkg.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
   class Pkg < Uncompressed
     extend T::Sig
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".pkg", ".mkpg"]
diff --git a/Library/Homebrew/unpack_strategy/rar.rb b/Library/Homebrew/unpack_strategy/rar.rb
index bd2b8042bb..9a2be11326 100644
--- a/Library/Homebrew/unpack_strategy/rar.rb
+++ b/Library/Homebrew/unpack_strategy/rar.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
 
     include UnpackStrategy
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".rar"]
diff --git a/Library/Homebrew/unpack_strategy/self_extracting_executable.rb b/Library/Homebrew/unpack_strategy/self_extracting_executable.rb
index 0e99278711..a3ea1e8de1 100644
--- a/Library/Homebrew/unpack_strategy/self_extracting_executable.rb
+++ b/Library/Homebrew/unpack_strategy/self_extracting_executable.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
   class SelfExtractingExecutable < GenericUnar
     extend T::Sig
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       []
diff --git a/Library/Homebrew/unpack_strategy/sit.rb b/Library/Homebrew/unpack_strategy/sit.rb
index 687e7d0e64..d747cb3178 100644
--- a/Library/Homebrew/unpack_strategy/sit.rb
+++ b/Library/Homebrew/unpack_strategy/sit.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
   class Sit < GenericUnar
     extend T::Sig
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".sit"]
diff --git a/Library/Homebrew/unpack_strategy/subversion.rb b/Library/Homebrew/unpack_strategy/subversion.rb
index dd3355825b..4097f13610 100644
--- a/Library/Homebrew/unpack_strategy/subversion.rb
+++ b/Library/Homebrew/unpack_strategy/subversion.rb
@@ -6,8 +6,6 @@ require_relative "directory"
 module UnpackStrategy
   # Strategy for unpacking Subversion repositories.
   class Subversion < Directory
-    using Magic
-
     def self.can_extract?(path)
       super && (path/".svn").directory?
     end
diff --git a/Library/Homebrew/unpack_strategy/tar.rb b/Library/Homebrew/unpack_strategy/tar.rb
index 9b0797cfa1..42ca323d33 100644
--- a/Library/Homebrew/unpack_strategy/tar.rb
+++ b/Library/Homebrew/unpack_strategy/tar.rb
@@ -11,8 +11,6 @@ module UnpackStrategy
     include UnpackStrategy
     extend SystemCommand::Mixin
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [
diff --git a/Library/Homebrew/unpack_strategy/ttf.rb b/Library/Homebrew/unpack_strategy/ttf.rb
index 38b44879de..bd0da5ea76 100644
--- a/Library/Homebrew/unpack_strategy/ttf.rb
+++ b/Library/Homebrew/unpack_strategy/ttf.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
   class Ttf < Uncompressed
     extend T::Sig
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".ttc", ".ttf"]
diff --git a/Library/Homebrew/unpack_strategy/xar.rb b/Library/Homebrew/unpack_strategy/xar.rb
index ce35a0683a..4707a602d5 100644
--- a/Library/Homebrew/unpack_strategy/xar.rb
+++ b/Library/Homebrew/unpack_strategy/xar.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
 
     include UnpackStrategy
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".xar"]
diff --git a/Library/Homebrew/unpack_strategy/xz.rb b/Library/Homebrew/unpack_strategy/xz.rb
index 61e1b2c3ab..cc450d51d6 100644
--- a/Library/Homebrew/unpack_strategy/xz.rb
+++ b/Library/Homebrew/unpack_strategy/xz.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
 
     include UnpackStrategy
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".xz"]
diff --git a/Library/Homebrew/unpack_strategy/zip.rb b/Library/Homebrew/unpack_strategy/zip.rb
index c8925c96c6..85ef33cbbb 100644
--- a/Library/Homebrew/unpack_strategy/zip.rb
+++ b/Library/Homebrew/unpack_strategy/zip.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
 
     include UnpackStrategy
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".zip"]
diff --git a/Library/Homebrew/unpack_strategy/zstd.rb b/Library/Homebrew/unpack_strategy/zstd.rb
index 4e77184977..c5f0b2a6b9 100644
--- a/Library/Homebrew/unpack_strategy/zstd.rb
+++ b/Library/Homebrew/unpack_strategy/zstd.rb
@@ -8,8 +8,6 @@ module UnpackStrategy
 
     include UnpackStrategy
 
-    using Magic
-
     sig { returns(T::Array[String]) }
     def self.extensions
       [".zst"]
diff --git a/Library/Homebrew/upgrade.rb b/Library/Homebrew/upgrade.rb
index 83fe6329e2..314adea386 100644
--- a/Library/Homebrew/upgrade.rb
+++ b/Library/Homebrew/upgrade.rb
@@ -310,10 +310,10 @@ module Homebrew
       if upgradeable_dependents.blank?
         ohai "No outdated dependents to upgrade!" unless dry_run
       else
-        dependent_plural = Utils.pluralize("dependent", upgradeable_dependents.count)
         formula_plural = Utils.pluralize("formula", installed_formulae.count, plural: "e")
         upgrade_verb = dry_run ? "Would upgrade" : "Upgrading"
-        ohai "#{upgrade_verb} #{upgradeable_dependents.count} #{dependent_plural} of upgraded #{formula_plural}:"
+        ohai "#{upgrade_verb} #{Utils.pluralize("dependent", upgradeable_dependents.count,
+                                                include_count: true)} of upgraded #{formula_plural}:"
         Upgrade.puts_no_installed_dependents_check_disable_message_if_not_already!
         formulae_upgrades = upgradeable_dependents.map do |f|
           name = f.full_specified_name
@@ -386,9 +386,8 @@ module Homebrew
       if reinstallable_broken_dependents.blank?
         ohai "No broken dependents to reinstall!"
       else
-        count = reinstallable_broken_dependents.count
-        plural = Utils.pluralize("dependent", reinstallable_broken_dependents.count)
-        ohai "Reinstalling #{count} #{plural} with broken linkage from source:"
+        ohai "Reinstalling #{Utils.pluralize("dependent", reinstallable_broken_dependents.count,
+                                             include_count: true)} with broken linkage from source:"
         Upgrade.puts_no_installed_dependents_check_disable_message_if_not_already!
         puts reinstallable_broken_dependents.map(&:full_specified_name)
                                             .join(", ")
diff --git a/Library/Homebrew/utils.rb b/Library/Homebrew/utils.rb
index a0bf5fdcec..a620e38c69 100644
--- a/Library/Homebrew/utils.rb
+++ b/Library/Homebrew/utils.rb
@@ -126,10 +126,14 @@ module Utils
 
   # A lightweight alternative to `ActiveSupport::Inflector.pluralize`:
   # Combines `stem` with the `singular` or `plural` suffix based on `count`.
-  sig { params(stem: String, count: Integer, plural: String, singular: String).returns(String) }
-  def self.pluralize(stem, count, plural: "s", singular: "")
+  # Adds a prefix of the count value if `include_count` is set to true.
+  sig {
+    params(stem: String, count: Integer, plural: String, singular: String, include_count: T::Boolean).returns(String)
+  }
+  def self.pluralize(stem, count, plural: "s", singular: "", include_count: false)
+    prefix = include_count ? "#{count} " : ""
     suffix = (count == 1) ? singular : plural
-    "#{stem}#{suffix}"
+    "#{prefix}#{stem}#{suffix}"
   end
 
   sig { params(author: String).returns({ email: String, name: String }) }
diff --git a/Library/Homebrew/utils/analytics.rb b/Library/Homebrew/utils/analytics.rb
index edaaf7662b..4ce8599335 100644
--- a/Library/Homebrew/utils/analytics.rb
+++ b/Library/Homebrew/utils/analytics.rb
@@ -12,7 +12,7 @@ module Utils
   # @api private
   module Analytics
     INFLUX_BUCKET = "analytics"
-    INFLUX_TOKEN = "9eMkCRwRWS7xjPR_HbF5tBffKmnyRFSup7rq41tHZLOpnBsjVtRFd-y9R_P9OCcB3kr1ftDEzxcxTehcufy1SQ=="
+    INFLUX_TOKEN = "sSE5_ENBUUhuh3vL3QDi6Rqo96DDZznBYoBT_TEdYnjj8IH2H_1PQD2qkAP0nnSwEIKvfQvW3Sb24GWYT35jqg=="
     INFLUX_HOST = "https://europe-west1-1.gcp.cloud2.influxdata.com"
     INFLUX_ORG = "9a707721bb47fc02"
 
@@ -72,27 +72,36 @@ module Utils
       end
 
       sig {
-        params(measurement: Symbol, package_and_options: String, on_request: T::Boolean,
-               additional_tags: T::Hash[Symbol, T.untyped]).void
+        params(measurement: Symbol, package_name: String, tap_name: String, on_request: T::Boolean,
+               options: String).void
       }
-      def report_influx(measurement, package_and_options, on_request, additional_tags = {})
-        # convert on_request to a boolean
+      def report_influx(measurement, package_name:, tap_name:, on_request:, options:)
+        # ensure on_request is a boolean
         on_request = on_request ? true : false
 
-        # Append general information to device information
-        tags = additional_tags.merge(package_and_options: package_and_options, on_request: on_request)
-                              .compact
-                              .map { |k, v| "#{k}=#{v.to_s.sub(" ", "\\ ")}" } # convert to key/value parameters
-                              .join(",")
+        # ensure options are removed (by `.compact` below) if empty
+        options = nil if options.blank?
+
+        # Tags are always implicitly strings and must have low cardinality.
+        tags = default_tags_influx.merge(on_request: on_request)
+                                  .map { |k, v| "#{k}=#{v}" }
+                                  .join(",")
+
+        # Fields need explicitly wrapped with quotes and can have high cardinality.
+        fields = default_fields_influx.merge(package: package_name, tap_name: tap_name, options: options)
+                                      .compact
+                                      .map { |k, v| %Q(#{k}="#{v}") }
+                                      .join(",")
 
         args = [
           "--max-time", "3",
+          "--header", "Authorization: Token #{INFLUX_TOKEN}",
           "--header", "Content-Type: text/plain; charset=utf-8",
           "--header", "Accept: application/json",
-          "--header", "Authorization: Token #{INFLUX_TOKEN}",
-          "--data-raw", "#{measurement},#{tags} count=1i #{Time.now.to_i}"
+          "--data-binary", "#{measurement},#{tags} #{fields} #{Time.now.to_i}"
         ]
 
+        # Second precision is highest we can do and has the lowest performance cost.
         url = "#{INFLUX_HOST}/api/v2/write?bucket=#{INFLUX_BUCKET}&precision=s"
         deferred_curl(url, args)
       end
@@ -111,10 +120,20 @@ module Utils
         end
       end
 
-      sig { params(measurement: Symbol, package_and_options: String, on_request: T::Boolean).void }
-      def report_event(measurement, package_and_options, on_request: false)
+      sig {
+        params(measurement: Symbol, package_name: String, tap_name: String,
+               on_request: T::Boolean, options: String).void
+      }
+      def report_event(measurement, package_name:, tap_name:, on_request:, options: "")
+        report_influx_event(measurement, package_name: package_name, tap_name: tap_name, on_request: on_request,
+options: options)
+
+        package_and_options = package_name
+        if tap_name.present? && tap_name != "homebrew/core" && tap_name != "homebrew/cask"
+          package_and_options = "#{tap_name}/#{package_and_options}"
+        end
+        package_and_options = "#{package_and_options} #{options}" if options.present?
         report_google_event(measurement, package_and_options, on_request: on_request)
-        report_influx_event(measurement, package_and_options, on_request: on_request)
       end
 
       sig { params(category: Symbol, action: String, on_request: T::Boolean).void }
@@ -138,11 +157,15 @@ module Utils
                       ev: nil)
       end
 
-      sig { params(measurement: Symbol, package_and_options: String, on_request: T::Boolean).void }
-      def report_influx_event(measurement, package_and_options, on_request: false)
+      sig {
+        params(measurement: Symbol, package_name: String, tap_name: String, on_request: T::Boolean,
+               options: String).void
+      }
+      def report_influx_event(measurement, package_name:, tap_name:, on_request: false, options: "")
         return if not_this_run? || disabled?
 
-        report_influx(measurement, package_and_options, on_request, additional_tags_influx)
+        report_influx(measurement, package_name: package_name, tap_name: tap_name, on_request: on_request,
+options: options)
       end
 
       sig { params(exception: BuildError).void }
@@ -171,16 +194,15 @@ module Utils
       def report_influx_error(exception)
         return if not_this_run? || disabled?
 
-        return unless exception.formula.tap
-        return unless exception.formula.tap.should_report_analytics?
+        formula = exception.formula
+        return unless formula
 
-        formula_full_name = exception.formula.full_name
-        package_and_options = if (options = exception.options.to_a.map(&:to_s).join(" ").presence)
-          "#{formula_full_name} #{options}".strip
-        else
-          formula_full_name
-        end
-        report_influx_event(:build_error, package_and_options)
+        tap = formula.tap
+        return unless tap
+        return unless tap.should_report_analytics?
+
+        options = exception.options.to_a.map(&:to_s).join(" ")
+        report_influx_event(:build_error, package_name: formula.name, tap_name: tap.name, options: options)
       end
 
       def messages_displayed?
@@ -322,9 +344,10 @@ module Utils
       end
       alias generic_arch_label_google arch_label_google
 
-      def clear_additional_tags_cache
+      def clear_cache
         remove_instance_variable(:@label_google) if instance_variable_defined?(:@label_google)
-        remove_instance_variable(:@additional_tags_influx) if instance_variable_defined?(:@additional_tags_influx)
+        remove_instance_variable(:@default_tags_influx) if instance_variable_defined?(:@default_tags_influx)
+        remove_instance_variable(:@default_fields_influx) if instance_variable_defined?(:@default_fields_influx)
       end
 
       sig { returns(String) }
@@ -339,25 +362,40 @@ module Utils
       end
 
       sig { returns(T::Hash[Symbol, String]) }
-      def additional_tags_influx
-        @additional_tags_influx ||= begin
-          version = HOMEBREW_VERSION.match(/^[\d.]+/)[0]
-          version = "#{version}-dev" if HOMEBREW_VERSION.include?("-")
+      def default_tags_influx
+        @default_tags_influx ||= begin
+          # Only display default prefixes to reduce cardinality and improve privacy
           prefix = Homebrew.default_prefix? ? HOMEBREW_PREFIX.to_s : "custom-prefix"
 
-          # Cleanup quotes and patch/patchset versions to reduce cardinality.
-          os_version = OS_VERSION.tr('"', "")
-                                 .gsub(/(\d+\.\d+)(\.\d+)?(-\d)?/, '\1')
+          # Tags are always strings and must have low cardinality.
+          {
+            ci:             ENV["CI"].present?,
+            prefix:         prefix,
+            default_prefix: Homebrew.default_prefix?,
+            developer:      Homebrew::EnvConfig.developer?,
+            devcmdrun:      config_true?(:devcmdrun),
+            arch:           HOMEBREW_PHYSICAL_PROCESSOR,
+            os:             HOMEBREW_SYSTEM,
+          }
+        end
+      end
+
+      # remove os_version starting with " or number
+      # remove macOS patch release
+      sig { returns(T::Hash[Symbol, String]) }
+      def default_fields_influx
+        @default_fields_influx ||= begin
+          version = HOMEBREW_VERSION.match(/^[\d.]+/)[0]
+          version = "#{version}-dev" if HOMEBREW_VERSION.include?("-")
+
+          # Only include OS versions with an actual name.
+          os_name_and_version = if (os_version = OS_VERSION.presence) && os_version.downcase.match?(/^[a-z]/)
+            os_version
+          end
 
           {
             version:             version,
-            prefix:              prefix,
-            default_prefix:      Homebrew.default_prefix?,
-            ci:                  ENV["CI"].present?,
-            developer:           Homebrew::EnvConfig.developer?,
-            arch:                HOMEBREW_PHYSICAL_PROCESSOR,
-            os:                  HOMEBREW_SYSTEM,
-            os_name_and_version: os_version,
+            os_name_and_version: os_name_and_version,
           }
         end
       end
diff --git a/Library/Homebrew/utils/github/actions.rb b/Library/Homebrew/utils/github/actions.rb
index c255dec4a0..ed27283bb3 100644
--- a/Library/Homebrew/utils/github/actions.rb
+++ b/Library/Homebrew/utils/github/actions.rb
@@ -1,6 +1,7 @@
 # typed: true
 # frozen_string_literal: true
 
+require "securerandom"
 require "utils/tty"
 
 module GitHub
@@ -18,6 +19,24 @@ module GitHub
             .gsub("\r", "%0D")
     end
 
+    sig { params(name: String, value: String).returns(String) }
+    def self.format_multiline_string(name, value)
+      # Format multiline strings for environment files
+      # See https://docs.github.com/en/actions/using-workflows/workflow-commands-for-github-actions#multiline-strings
+
+      delimiter = "ghadelimiter_#{SecureRandom.uuid}"
+
+      if name.include?(delimiter) || value.include?(delimiter)
+        raise "`name` and `value` must not contain the delimiter"
+      end
+
+      <<~EOS
+        #{name}<<#{delimiter}
+        #{value}
+        #{delimiter}
+      EOS
+    end
+
     # Helper class for formatting annotations on GitHub Actions.
     class Annotation
       extend T::Sig
diff --git a/Library/Homebrew/vendor/bundle/bundler/setup.rb b/Library/Homebrew/vendor/bundle/bundler/setup.rb
index c504edc585..dab3881c96 100644
--- a/Library/Homebrew/vendor/bundle/bundler/setup.rb
+++ b/Library/Homebrew/vendor/bundle/bundler/setup.rb
@@ -119,6 +119,8 @@ $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/sorbet-static-and-runtime-0.5.10461/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/thor-1.2.1/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/spoom-1.1.11/lib")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/universal-darwin-21/#{Gem.extension_api_version}/stackprof-0.2.24")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/stackprof-0.2.24/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/yard-0.9.26/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/yard-sorbet-0.6.1/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/tapioca-0.7.3/lib")
diff --git a/completions/bash/brew b/completions/bash/brew
index 599dd1f915..cad55301f8 100644
--- a/completions/bash/brew
+++ b/completions/bash/brew
@@ -1619,6 +1619,22 @@ _brew_pin() {
   __brew_complete_installed_formulae
 }
 
+_brew_postgresql_upgrade_database() {
+  local cur="${COMP_WORDS[COMP_CWORD]}"
+  case "${cur}" in
+    -*)
+      __brewcomp "
+      --debug
+      --help
+      --quiet
+      --verbose
+      "
+      return
+      ;;
+    *) ;;
+  esac
+}
+
 _brew_postinstall() {
   local cur="${COMP_WORDS[COMP_CWORD]}"
   case "${cur}" in
@@ -1697,6 +1713,7 @@ _brew_pr_pull() {
       --keep-old
       --message
       --no-autosquash
+      --no-cherry-pick
       --no-commit
       --no-upload
       --quiet
@@ -2639,6 +2656,7 @@ _brew() {
     options) _brew_options ;;
     outdated) _brew_outdated ;;
     pin) _brew_pin ;;
+    postgresql-upgrade-database) _brew_postgresql_upgrade_database ;;
     postinstall) _brew_postinstall ;;
     pr-automerge) _brew_pr_automerge ;;
     pr-publish) _brew_pr_publish ;;
diff --git a/completions/fish/brew.fish b/completions/fish/brew.fish
index 644584a378..d2f9c719b2 100644
--- a/completions/fish/brew.fish
+++ b/completions/fish/brew.fish
@@ -1122,6 +1122,13 @@ __fish_brew_complete_arg 'pin' -l verbose -d 'Make some output more verbose'
 __fish_brew_complete_arg 'pin' -a '(__fish_brew_suggest_formulae_installed)'
 
 
+__fish_brew_complete_cmd 'postgresql-upgrade-database' 'Upgrades the database for the `postgresql` formula'
+__fish_brew_complete_arg 'postgresql-upgrade-database' -l debug -d 'Display any debugging information'
+__fish_brew_complete_arg 'postgresql-upgrade-database' -l help -d 'Show this message'
+__fish_brew_complete_arg 'postgresql-upgrade-database' -l quiet -d 'Make some output more quiet'
+__fish_brew_complete_arg 'postgresql-upgrade-database' -l verbose -d 'Make some output more verbose'
+
+
 __fish_brew_complete_cmd 'postinstall' 'Rerun the post-install steps for formula'
 __fish_brew_complete_arg 'postinstall' -l debug -d 'Display any debugging information'
 __fish_brew_complete_arg 'postinstall' -l help -d 'Show this message'
@@ -1169,6 +1176,7 @@ __fish_brew_complete_arg 'pr-pull' -l ignore-missing-artifacts -d 'Comma-separat
 __fish_brew_complete_arg 'pr-pull' -l keep-old -d 'If the formula specifies a rebuild version, attempt to preserve its value in the generated DSL'
 __fish_brew_complete_arg 'pr-pull' -l message -d 'Message to include when autosquashing revision bumps, deletions, and rebuilds'
 __fish_brew_complete_arg 'pr-pull' -l no-autosquash -d 'Skip automatically reformatting and rewording commits in the pull request to our preferred format'
+__fish_brew_complete_arg 'pr-pull' -l no-cherry-pick -d 'Do not cherry-pick commits from the pull request branch'
 __fish_brew_complete_arg 'pr-pull' -l no-commit -d 'Do not generate a new commit before uploading'
 __fish_brew_complete_arg 'pr-pull' -l no-upload -d 'Download the bottles but don\'t upload them'
 __fish_brew_complete_arg 'pr-pull' -l quiet -d 'Make some output more quiet'
diff --git a/completions/internal_commands_list.txt b/completions/internal_commands_list.txt
index 15d6a01c08..ce9b70c9c6 100644
--- a/completions/internal_commands_list.txt
+++ b/completions/internal_commands_list.txt
@@ -67,6 +67,7 @@ nodenv-sync
 options
 outdated
 pin
+postgresql-upgrade-database
 postinstall
 pr-automerge
 pr-publish
diff --git a/completions/zsh/_brew b/completions/zsh/_brew
index c3723ddf3e..a0df052392 100644
--- a/completions/zsh/_brew
+++ b/completions/zsh/_brew
@@ -188,6 +188,7 @@ __brew_internal_commands() {
     'options:Show install options specific to formula'
     'outdated:List installed casks and formulae that have an updated version available'
     'pin:Pin the specified formula, preventing them from being upgraded when issuing the `brew upgrade` formula command'
+    'postgresql-upgrade-database:Upgrades the database for the `postgresql` formula'
     'postinstall:Rerun the post-install steps for formula'
     'pr-automerge:Find pull requests that can be automatically merged using `brew pr-publish`'
     'pr-publish:Publish bottles for a pull request with GitHub Actions'
@@ -1375,6 +1376,15 @@ _brew_pin() {
     '*::installed_formula:__brew_installed_formulae'
 }
 
+# brew postgresql-upgrade-database
+_brew_postgresql_upgrade_database() {
+  _arguments \
+    '--debug[Display any debugging information]' \
+    '--help[Show this message]' \
+    '--quiet[Make some output more quiet]' \
+    '--verbose[Make some output more verbose]'
+}
+
 # brew postinstall
 _brew_postinstall() {
   _arguments \
@@ -1431,6 +1441,7 @@ _brew_pr_pull() {
     '--keep-old[If the formula specifies a rebuild version, attempt to preserve its value in the generated DSL]' \
     '(--no-autosquash)--message[Message to include when autosquashing revision bumps, deletions, and rebuilds]' \
     '(--message)--no-autosquash[Skip automatically reformatting and rewording commits in the pull request to our preferred format]' \
+    '--no-cherry-pick[Do not cherry-pick commits from the pull request branch]' \
     '--no-commit[Do not generate a new commit before uploading]' \
     '--no-upload[Download the bottles but don'\''t upload them]' \
     '--quiet[Make some output more quiet]' \
diff --git a/docs/Manpage.md b/docs/Manpage.md
index 652e3bb504..6da9b531f4 100644
--- a/docs/Manpage.md
+++ b/docs/Manpage.md
@@ -517,6 +517,10 @@ information is displayed in interactive shells, and suppressed otherwise.
 Pin the specified *`formula`*, preventing them from being upgraded when
 issuing the `brew upgrade` *`formula`* command. See also `unpin`.
 
+### `postgresql-upgrade-database`
+
+Upgrades the database for the `postgresql` formula.
+
 ### `postinstall` *`installed_formula`* [...]
 
 Rerun the post-install steps for *`formula`*.
@@ -1360,6 +1364,8 @@ Requires write access to the repository.
   Download the bottles but don't upload them.
 * `--no-commit`:
   Do not generate a new commit before uploading.
+* `--no-cherry-pick`:
+  Do not cherry-pick commits from the pull request branch.
 * `-n`, `--dry-run`:
   Print what would be done rather than doing it.
 * `--clean`:
diff --git a/docs/README.md b/docs/README.md
index dad84f9f5a..d112ff825e 100644
--- a/docs/README.md
+++ b/docs/README.md
@@ -55,6 +55,8 @@
 - [Prose Style Guidelines](Prose-Style-Guidelines.md)
 - [Type Checking with Sorbet](Typechecking.md)
 
+- [Ruby API Documentation](https://rubydoc.brew.sh) (e.g. for `Formula` etc.)
+
 ## Maintainers
 
 - [New Maintainer Checklist](New-Maintainer-Checklist.md)
@@ -68,7 +70,6 @@
 - [Brew Test Bot for Maintainers](Brew-Test-Bot-For-Core-Contributors.md)
 - [Common Issues for Maintainers](Common-Issues-for-Core-Contributors.md)
 - [Releases](Releases.md)
-- [Developer/Internal API Documentation](https://rubydoc.brew.sh)
 
 ## Governance
 
diff --git a/manpages/brew.1 b/manpages/brew.1
index b26da27a09..ae9803b988 100644
--- a/manpages/brew.1
+++ b/manpages/brew.1
@@ -719,6 +719,9 @@ Also include outdated casks including those with \fBauto_updates true\fR\.
 .SS "\fBpin\fR \fIinstalled_formula\fR [\.\.\.]"
 Pin the specified \fIformula\fR, preventing them from being upgraded when issuing the \fBbrew upgrade\fR \fIformula\fR command\. See also \fBunpin\fR\.
 .
+.SS "\fBpostgresql\-upgrade\-database\fR"
+Upgrades the database for the \fBpostgresql\fR formula\.
+.
 .SS "\fBpostinstall\fR \fIinstalled_formula\fR [\.\.\.]"
 Rerun the post\-install steps for \fIformula\fR\.
 .
@@ -1944,6 +1947,10 @@ Download the bottles but don\'t upload them\.
 Do not generate a new commit before uploading\.
 .
 .TP
+\fB\-\-no\-cherry\-pick\fR
+Do not cherry\-pick commits from the pull request branch\.
+.
+.TP
 \fB\-n\fR, \fB\-\-dry\-run\fR
 Print what would be done rather than doing it\.
 .