diff --git a/Library/Homebrew/.parlour b/Library/Homebrew/.parlour
new file mode 100644
index 0000000000..1fe16333dc
--- /dev/null
+++ b/Library/Homebrew/.parlour
@@ -0,0 +1,10 @@
+parser: false
+
+output_file:
+  rbi: sorbet/rbi/parlour.rbi
+
+relative_requires:
+  - sorbet/parlour.rb
+
+plugins:
+  Attr: {}
diff --git a/Library/Homebrew/Gemfile b/Library/Homebrew/Gemfile
index a434b3a5c9..c83f920267 100644
--- a/Library/Homebrew/Gemfile
+++ b/Library/Homebrew/Gemfile
@@ -24,6 +24,7 @@ gem "simplecov-cobertura", require: false
 gem "warning", require: false
 
 group :sorbet, optional: true do
+  gem "parlour", require: false
   gem "rspec-sorbet", require: false
   gem "sorbet", require: false
   gem "sorbet-runtime", require: false
diff --git a/Library/Homebrew/Gemfile.lock b/Library/Homebrew/Gemfile.lock
index 1bcb62f2b7..99689717d8 100644
--- a/Library/Homebrew/Gemfile.lock
+++ b/Library/Homebrew/Gemfile.lock
@@ -188,6 +188,7 @@ DEPENDENCIES
   mechanize
   minitest
   parallel_tests
+  parlour
   patchelf
   plist
   ronn
diff --git a/Library/Homebrew/dev-cmd/typecheck.rb b/Library/Homebrew/dev-cmd/typecheck.rb
index 07ee66aae3..73242d0a5b 100644
--- a/Library/Homebrew/dev-cmd/typecheck.rb
+++ b/Library/Homebrew/dev-cmd/typecheck.rb
@@ -61,6 +61,7 @@ module Homebrew
 
         ohai "Updating Tapioca RBI files..."
         system "bundle", "exec", "tapioca", "sync", "--exclude", *excluded_gems
+        system "bundle", "exec", "parlour"
         system "bundle", "exec", "srb", "rbi", "hidden-definitions"
         system "bundle", "exec", "srb", "rbi", "todo"
 
diff --git a/Library/Homebrew/extend/hash_validator.rbi b/Library/Homebrew/extend/hash_validator.rbi
new file mode 100644
index 0000000000..715b783813
--- /dev/null
+++ b/Library/Homebrew/extend/hash_validator.rbi
@@ -0,0 +1,6 @@
+# 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/time.rbi b/Library/Homebrew/extend/time.rbi
new file mode 100644
index 0000000000..ab1c7254f9
--- /dev/null
+++ b/Library/Homebrew/extend/time.rbi
@@ -0,0 +1,9 @@
+# typed: strict
+
+class Time
+  sig { returns(T.any(Integer, Float)) }
+  def remaining; end
+
+  sig { returns(T.any(Integer, Float)) }
+  def remaining!; end
+end
diff --git a/Library/Homebrew/sorbet/config b/Library/Homebrew/sorbet/config
index 024ba458ec..02fbf5ab02 100644
--- a/Library/Homebrew/sorbet/config
+++ b/Library/Homebrew/sorbet/config
@@ -6,6 +6,3 @@
 
 --ignore
 /test/.gem
-
---dsl-plugins
-sorbet/triggers.yml
diff --git a/Library/Homebrew/sorbet/parlour.rb b/Library/Homebrew/sorbet/parlour.rb
new file mode 100644
index 0000000000..c33a64dc8c
--- /dev/null
+++ b/Library/Homebrew/sorbet/parlour.rb
@@ -0,0 +1,42 @@
+# frozen_string_literal: true
+# typed: true
+
+require_relative "../warnings"
+Warnings.ignore :parser_syntax do
+  require "parser/current"
+end
+
+module Homebrew
+  module Parlour
+    extend T::Sig
+
+    ROOT_DIR = T.let(Pathname(__dir__).parent.realpath.freeze, Pathname)
+
+    sig { returns(T::Array[Parser::AST::Node]) }
+    def self.ast_list
+      @@ast_list ||= begin
+        ast_list = []
+        parser = Parser::CurrentRuby.new
+
+        ROOT_DIR.find do |path|
+          Find.prune if path.directory? && %w[sorbet shims test vendor].any? { |subdir| path == ROOT_DIR/subdir }
+
+          Find.prune if path.file? && path.extname != ".rb"
+
+          next unless path.file?
+
+          buffer = Parser::Source::Buffer.new(path, source: path.read)
+
+          parser.reset
+          ast = parser.parse(buffer)
+          ast_list << ast if ast
+        end
+
+        ast_list
+      end
+    end
+  end
+end
+
+require "parlour"
+require_relative "parlour/attr"
diff --git a/Library/Homebrew/sorbet/parlour/attr.rb b/Library/Homebrew/sorbet/parlour/attr.rb
new file mode 100644
index 0000000000..8f8c4bf8fd
--- /dev/null
+++ b/Library/Homebrew/sorbet/parlour/attr.rb
@@ -0,0 +1,110 @@
+# frozen_string_literal: true
+# typed: strict
+
+class Attr < Parlour::Plugin
+  sig { override.params(root: Parlour::RbiGenerator::Namespace).void }
+  def generate(root)
+    tree = T.let([], T::Array[T.untyped])
+    Homebrew::Parlour.ast_list.each do |node|
+      tree += find_custom_attr(node)
+    end
+    process_custom_attr(tree, root)
+  end
+
+  sig { override.returns(T.nilable(String)) }
+  def strictness
+    return "strict"
+  end
+
+  private
+
+  sig { params(node: Parser::AST::Node, list: T::Array[String]).returns(T::Array[String]) }
+  def traverse_module_name(node, list = [])
+    parent, name = node.children
+    list = traverse_module_name(parent, list) if parent
+    list << name.to_s
+    list
+  end
+
+  sig { params(node: T.nilable(Parser::AST::Node)).returns(T.nilable(String)) }
+  def extract_module_name(node)
+    return if node.nil?
+
+    traverse_module_name(node).join("::")
+  end
+    
+  sig { params(node: Parser::AST::Node).returns(T::Array[T.untyped]) }
+  def find_custom_attr(node)
+    tree = T.let([], T::Array[T.untyped])
+    children = node.children.dup
+
+    if node.type == :begin
+      children.each do |child|
+        subtree = find_custom_attr(child)
+        tree += subtree unless subtree.empty?
+      end
+    elsif node.type == :sclass
+      subtree = find_custom_attr(node.children[1])
+      return tree if subtree.empty?
+      
+      tree << [:sclass, subtree]
+    elsif node.type == :class || node.type == :module
+      element = []
+      if node.type == :class
+        element << :class
+        element << extract_module_name(children.shift)
+        element << extract_module_name(children.shift)
+      elsif node.type == :module
+        element << :module
+        element << extract_module_name(children.shift)
+      end
+
+      body = children.shift
+      return tree if body.nil?
+
+      subtree = find_custom_attr(body)
+      return tree if subtree.empty?
+
+      element << subtree
+      tree << element
+    elsif node.type == :send && children.shift.nil?
+      method_name = children.shift
+      if method_name == :attr_rw || method_name == :attr_predicate
+        children.each do |name_node|
+          tree << [method_name, name_node.children.first.to_s]
+        end
+      end
+    end
+
+    tree
+  end
+
+  sig { params(tree: T::Array[T.untyped], namespace: Parlour::RbiGenerator::Namespace, sclass: T::Boolean).void }
+  def process_custom_attr(tree, namespace, sclass: false)
+    tree.each do |node|
+      type = node.shift
+      case type
+      when :sclass
+        process_custom_attr(node.shift, namespace, sclass: true)
+      when :class
+        class_namespace = namespace.create_class(node.shift, superclass: node.shift)
+        process_custom_attr(node.shift, class_namespace)
+      when :module
+        module_namespace = namespace.create_module(node.shift)
+        process_custom_attr(node.shift, module_namespace)
+      when :attr_rw
+        name = node.shift
+        name = "self.#{name}" if sclass
+        namespace.create_method(name, parameters: [
+          Parlour::RbiGenerator::Parameter.new("arg", type: "T.untyped", default: "T.unsafe(nil)")
+        ], return_type: "T.untyped")
+      when :attr_predicate
+        name = node.shift
+        name = "self.#{name}" if sclass
+        namespace.create_method(name, return_type: "T::Boolean")
+      else
+        raise "Malformed tree."
+      end
+    end
+  end
+end
diff --git a/Library/Homebrew/sorbet/plugins/attr_predicate.rb b/Library/Homebrew/sorbet/plugins/attr_predicate.rb
deleted file mode 100644
index 2559705d5d..0000000000
--- a/Library/Homebrew/sorbet/plugins/attr_predicate.rb
+++ /dev/null
@@ -1,13 +0,0 @@
-# typed: strict
-# frozen_string_literal: true
-
-source = ARGV[5]
-
-source.scan(/:([^?]+\?)/).flatten.each do |method|
-  puts <<~RUBY
-    # typed: strict
-
-    sig { returns(T::Boolean) }
-    def #{method}; end
-  RUBY
-end
diff --git a/Library/Homebrew/sorbet/plugins/attr_rw.rb b/Library/Homebrew/sorbet/plugins/attr_rw.rb
deleted file mode 100644
index 2363d3bffa..0000000000
--- a/Library/Homebrew/sorbet/plugins/attr_rw.rb
+++ /dev/null
@@ -1,13 +0,0 @@
-# typed: strict
-# frozen_string_literal: true
-
-source = ARGV[5]
-
-source.scan(/:([^\s,]+)/).flatten.each do |method|
-  puts <<~RUBY
-    # typed: strict
-
-    sig { params(arg: T.untyped).returns(T.untyped) }
-    def #{method}(arg = T.unsafe(nil)); end
-  RUBY
-end
diff --git a/Library/Homebrew/sorbet/plugins/def_delegator.rb b/Library/Homebrew/sorbet/plugins/def_delegator.rb
deleted file mode 100644
index 7eea2d6bd0..0000000000
--- a/Library/Homebrew/sorbet/plugins/def_delegator.rb
+++ /dev/null
@@ -1,17 +0,0 @@
-# typed: strict
-# frozen_string_literal: true
-
-source = ARGV[5]
-
-match = source.match(/\s*def_delegator\s+.*:(?<method>[^:]+)\s*\Z/m)
-
-raise if match.nil?
-
-method = match[:method]
-
-puts <<~RUBY
-  # typed: strict
-
-  sig {params(arg0: T.untyped, blk: T.untyped).returns(T.untyped)}
-  def #{method}(*arg0, &blk); end
-RUBY
diff --git a/Library/Homebrew/sorbet/plugins/def_delegators.rb b/Library/Homebrew/sorbet/plugins/def_delegators.rb
deleted file mode 100644
index ac09880d3c..0000000000
--- a/Library/Homebrew/sorbet/plugins/def_delegators.rb
+++ /dev/null
@@ -1,17 +0,0 @@
-# typed: strict
-# frozen_string_literal: true
-
-source = ARGV[5]
-
-symbols = source.scan(/:[^\s,]+/)
-
-_, *methods = symbols.map { |s| s.delete_prefix(":") }
-
-methods.each do |method|
-  puts <<~RUBY
-    # typed: strict
-
-    sig {params(arg0: T.untyped, blk: T.untyped).returns(T.untyped)}
-    def #{method}(*arg0, &blk); end
-  RUBY
-end
diff --git a/Library/Homebrew/sorbet/plugins/delegate.rb b/Library/Homebrew/sorbet/plugins/delegate.rb
deleted file mode 100644
index 8a249d188c..0000000000
--- a/Library/Homebrew/sorbet/plugins/delegate.rb
+++ /dev/null
@@ -1,21 +0,0 @@
-# typed: strict
-# frozen_string_literal: true
-
-source = ARGV[5]
-
-methods = if (single = source[/delegate\s+([^:]+):\s+/, 1])
-  [single]
-else
-  multiple = source[/delegate\s+\[(.*?)\]\s+=>\s+/m, 1]
-  non_comments = multiple.gsub(/\#.*$/, "")
-  non_comments.scan(/:([^:,\s]+)/).flatten
-end
-
-methods.each do |method|
-  puts <<~RUBY
-    # typed: strict
-
-    sig {params(arg0: T.untyped, blk: T.untyped).returns(T.untyped)}
-    def #{method}(*arg0, &blk); end
-  RUBY
-end
diff --git a/Library/Homebrew/sorbet/plugins/using.rb b/Library/Homebrew/sorbet/plugins/using.rb
deleted file mode 100644
index 288c4c6c44..0000000000
--- a/Library/Homebrew/sorbet/plugins/using.rb
+++ /dev/null
@@ -1,43 +0,0 @@
-# typed: strict
-# frozen_string_literal: true
-
-source = ARGV[5]
-
-case source[/\Ausing\s+(.*)\Z/, 1]
-when "Magic"
-  puts <<-RUBY
-    # typed: strict
-
-    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
-  RUBY
-when "HashValidator"
-  puts <<-RUBY
-    # typed: strict
-
-    class ::Hash
-      sig { params(valid_keys: T.untyped).void }
-      def assert_valid_keys!(*valid_keys); end
-    end
-  RUBY
-when "TimeRemaining"
-  puts <<-RUBY
-    # typed: strict
-
-    class ::Time
-      sig { returns(T.any(Integer, Float)) }
-      def remaining; end
-
-      sig { returns(T.any(Integer, Float)) }
-      def remaining!; end
-    end
-  RUBY
-end
diff --git a/Library/Homebrew/sorbet/rbi/parlour.rbi b/Library/Homebrew/sorbet/rbi/parlour.rbi
new file mode 100644
index 0000000000..ed2a0e5fcd
--- /dev/null
+++ b/Library/Homebrew/sorbet/rbi/parlour.rbi
@@ -0,0 +1,164 @@
+# typed: strict
+module Homebrew
+  class Cleanup
+    sig { returns(T::Boolean) }
+    def dry_run?; end
+
+    sig { returns(T::Boolean) }
+    def scrub?; end
+
+    sig { returns(T::Boolean) }
+    def prune?; end
+  end
+end
+
+module Debrew
+  sig { returns(T::Boolean) }
+  def self.active?; end
+end
+
+class Formula
+  sig { params(arg: T.untyped).returns(T.untyped) }
+  def self.desc(arg = T.unsafe(nil)); end
+
+  sig { params(arg: T.untyped).returns(T.untyped) }
+  def self.homepage(arg = T.unsafe(nil)); end
+
+  sig { params(arg: T.untyped).returns(T.untyped) }
+  def self.revision(arg = T.unsafe(nil)); end
+
+  sig { params(arg: T.untyped).returns(T.untyped) }
+  def self.version_scheme(arg = T.unsafe(nil)); end
+end
+
+class FormulaInstaller
+  sig { returns(T::Boolean) }
+  def installed_as_dependency?; end
+
+  sig { returns(T::Boolean) }
+  def installed_on_request?; end
+
+  sig { returns(T::Boolean) }
+  def show_summary_heading?; end
+
+  sig { returns(T::Boolean) }
+  def show_header?; end
+
+  sig { returns(T::Boolean) }
+  def force_bottle?; end
+
+  sig { returns(T::Boolean) }
+  def ignore_deps?; end
+
+  sig { returns(T::Boolean) }
+  def only_deps?; end
+
+  sig { returns(T::Boolean) }
+  def interactive?; end
+
+  sig { returns(T::Boolean) }
+  def git?; end
+
+  sig { returns(T::Boolean) }
+  def force?; end
+
+  sig { returns(T::Boolean) }
+  def keep_tmp?; end
+
+  sig { returns(T::Boolean) }
+  def verbose?; end
+
+  sig { returns(T::Boolean) }
+  def debug?; end
+
+  sig { returns(T::Boolean) }
+  def quiet?; end
+
+  sig { returns(T::Boolean) }
+  def hold_locks?; end
+end
+
+class Requirement
+  sig { params(arg: T.untyped).returns(T.untyped) }
+  def self.fatal(arg = T.unsafe(nil)); end
+
+  sig { params(arg: T.untyped).returns(T.untyped) }
+  def self.cask(arg = T.unsafe(nil)); end
+
+  sig { params(arg: T.untyped).returns(T.untyped) }
+  def self.download(arg = T.unsafe(nil)); end
+end
+
+class BottleSpecification
+  sig { params(arg: T.untyped).returns(T.untyped) }
+  def rebuild(arg = T.unsafe(nil)); end
+end
+
+class SystemCommand
+  sig { returns(T::Boolean) }
+  def sudo?; end
+
+  sig { returns(T::Boolean) }
+  def print_stdout?; end
+
+  sig { returns(T::Boolean) }
+  def print_stderr?; end
+
+  sig { returns(T::Boolean) }
+  def must_succeed?; end
+end
+
+module Cask
+  class Audit
+    sig { returns(T::Boolean) }
+    def appcast?; end
+
+    sig { returns(T::Boolean) }
+    def new_cask?; end
+
+    sig { returns(T::Boolean) }
+    def strict?; end
+
+    sig { returns(T::Boolean) }
+    def online?; end
+
+    sig { returns(T::Boolean) }
+    def token_conflicts?; end
+  end
+
+  class DSL
+    class Caveats < Base
+      sig { returns(T::Boolean) }
+      def discontinued?; end
+    end
+  end
+
+  class Installer
+    sig { returns(T::Boolean) }
+    def binaries?; end
+
+    sig { returns(T::Boolean) }
+    def force?; end
+
+    sig { returns(T::Boolean) }
+    def skip_cask_deps?; end
+
+    sig { returns(T::Boolean) }
+    def require_sha?; end
+
+    sig { returns(T::Boolean) }
+    def reinstall?; end
+
+    sig { returns(T::Boolean) }
+    def upgrade?; end
+
+    sig { returns(T::Boolean) }
+    def verbose?; end
+
+    sig { returns(T::Boolean) }
+    def installed_as_dependency?; end
+
+    sig { returns(T::Boolean) }
+    def quarantine?; end
+  end
+end
diff --git a/Library/Homebrew/sorbet/triggers.yml b/Library/Homebrew/sorbet/triggers.yml
deleted file mode 100644
index ccf1647ba4..0000000000
--- a/Library/Homebrew/sorbet/triggers.yml
+++ /dev/null
@@ -1,10 +0,0 @@
-ruby_extra_args:
-  - --disable-gems
-
-triggers:
-  using: sorbet/plugins/using.rb
-  attr_predicate: sorbet/plugins/attr_predicate.rb
-  attr_rw: sorbet/plugins/attr_rw.rb
-  def_delegator: sorbet/plugins/def_delegator.rb
-  def_delegators: sorbet/plugins/def_delegators.rb
-  delegate: sorbet/plugins/delegate.rb
diff --git a/Library/Homebrew/unpack_strategy.rbi b/Library/Homebrew/unpack_strategy.rbi
index d7550c56b2..55284f6668 100644
--- a/Library/Homebrew/unpack_strategy.rbi
+++ b/Library/Homebrew/unpack_strategy.rbi
@@ -3,3 +3,14 @@
 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