diff --git a/Library/Homebrew/Gemfile.lock b/Library/Homebrew/Gemfile.lock
index 91664c3983..ea65e95756 100644
--- a/Library/Homebrew/Gemfile.lock
+++ b/Library/Homebrew/Gemfile.lock
@@ -28,7 +28,7 @@ GEM
     hpricot (0.8.6)
     i18n (1.14.1)
       concurrent-ruby (~> 1.0)
-    json (2.6.3)
+    json (2.7.0)
     json_schemer (2.1.1)
       hana (~> 1.3)
       regexp_parser (~> 2.0)
diff --git a/Library/Homebrew/dev-cmd/typecheck.rb b/Library/Homebrew/dev-cmd/typecheck.rb
index 7f50f2d03e..649dd56d97 100644
--- a/Library/Homebrew/dev-cmd/typecheck.rb
+++ b/Library/Homebrew/dev-cmd/typecheck.rb
@@ -47,7 +47,7 @@ module Homebrew
       if update
         excluded_gems = [
           "did_you_mean", # RBI file is already provided by Sorbet
-          "webrobots", # RBI file is bugged
+          "json", # RBI file is already provided by Sorbet
           "sorbet-static-and-runtime", # Unnecessary RBI - remove this entry with Tapioca 0.8
         ]
         typed_overrides = [
diff --git a/Library/Homebrew/sorbet/rbi/gems/json@2.6.3.rbi b/Library/Homebrew/sorbet/rbi/gems/json@2.6.3.rbi
deleted file mode 100644
index 169cf4b68c..0000000000
--- a/Library/Homebrew/sorbet/rbi/gems/json@2.6.3.rbi
+++ /dev/null
@@ -1,101 +0,0 @@
-# typed: true
-
-# DO NOT EDIT MANUALLY
-# This is an autogenerated file for types exported from the `json` gem.
-# Please instead update this file by running `bin/tapioca gem json`.
-
-class Class < ::Module
-  def json_creatable?; end
-end
-
-module JSON
-  private
-
-  def dump(obj, anIO = T.unsafe(nil), limit = T.unsafe(nil)); end
-  def fast_generate(obj, opts = T.unsafe(nil)); end
-  def fast_unparse(obj, opts = T.unsafe(nil)); end
-  def generate(obj, opts = T.unsafe(nil)); end
-  def load(source, proc = T.unsafe(nil), options = T.unsafe(nil)); end
-  def load_file(filespec, opts = T.unsafe(nil)); end
-  def load_file!(filespec, opts = T.unsafe(nil)); end
-  def parse(source, opts = T.unsafe(nil)); end
-  def parse!(source, opts = T.unsafe(nil)); end
-  def pretty_generate(obj, opts = T.unsafe(nil)); end
-  def pretty_unparse(obj, opts = T.unsafe(nil)); end
-  def recurse_proc(result, &proc); end
-  def restore(source, proc = T.unsafe(nil), options = T.unsafe(nil)); end
-  def unparse(obj, opts = T.unsafe(nil)); end
-
-  class << self
-    def [](object, opts = T.unsafe(nil)); end
-    def create_fast_state; end
-    def create_id; end
-    def create_id=(new_value); end
-    def create_pretty_state; end
-    def deep_const_get(path); end
-    def dump(obj, anIO = T.unsafe(nil), limit = T.unsafe(nil)); end
-    def dump_default_options; end
-    def dump_default_options=(_arg0); end
-    def fast_generate(obj, opts = T.unsafe(nil)); end
-    def fast_unparse(obj, opts = T.unsafe(nil)); end
-    def generate(obj, opts = T.unsafe(nil)); end
-    def generator; end
-    def generator=(generator); end
-    def iconv(to, from, string); end
-    def load(source, proc = T.unsafe(nil), options = T.unsafe(nil)); end
-    def load_default_options; end
-    def load_default_options=(_arg0); end
-    def load_file(filespec, opts = T.unsafe(nil)); end
-    def load_file!(filespec, opts = T.unsafe(nil)); end
-    def parse(source, opts = T.unsafe(nil)); end
-    def parse!(source, opts = T.unsafe(nil)); end
-    def parser; end
-    def parser=(parser); end
-    def pretty_generate(obj, opts = T.unsafe(nil)); end
-    def pretty_unparse(obj, opts = T.unsafe(nil)); end
-    def recurse_proc(result, &proc); end
-    def restore(source, proc = T.unsafe(nil), options = T.unsafe(nil)); end
-    def state; end
-    def state=(_arg0); end
-    def unparse(obj, opts = T.unsafe(nil)); end
-  end
-end
-
-JSON::CREATE_ID_TLS_KEY = T.let(T.unsafe(nil), String)
-JSON::DEFAULT_CREATE_ID = T.let(T.unsafe(nil), String)
-
-class JSON::GenericObject < ::OpenStruct
-  def as_json(*_arg0); end
-  def to_hash; end
-  def to_json(*a); end
-  def |(other); end
-
-  class << self
-    def dump(obj, *args); end
-    def from_hash(object); end
-    def json_creatable=(_arg0); end
-    def json_creatable?; end
-    def json_create(data); end
-    def load(source, proc = T.unsafe(nil), opts = T.unsafe(nil)); end
-  end
-end
-
-class JSON::JSONError < ::StandardError
-  class << self
-    def wrap(exception); end
-  end
-end
-
-JSON::Parser = JSON::Ext::Parser
-JSON::State = JSON::Ext::Generator::State
-JSON::UnparserError = JSON::GeneratorError
-
-module Kernel
-  extend ::Forwardable
-
-  private
-
-  def JSON(object, *args); end
-  def j(*objs); end
-  def jj(*objs); end
-end
diff --git a/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi b/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi
index bed3a6b8c0..0578e860bb 100644
--- a/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi
+++ b/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi
@@ -3336,6 +3336,8 @@ end
 
 class Class
   def any_instance(); end
+
+  def json_creatable?(); end
 end
 
 class Complex
@@ -5712,6 +5714,18 @@ class JSON::Ext::Generator::State
   def escape_slash=(escape_slash); end
 
   def escape_slash?(); end
+
+  def script_safe(); end
+
+  def script_safe=(script_safe); end
+
+  def script_safe?(); end
+
+  def strict(); end
+
+  def strict=(strict); end
+
+  def strict?(); end
 end
 
 class JSON::Ext::Generator::State
@@ -5722,6 +5736,22 @@ class JSON::Ext::Parser
   def initialize(*arg); end
 end
 
+JSON::Parser = JSON::Ext::Parser
+
+JSON::State = JSON::Ext::Generator::State
+
+JSON::UnparserError = JSON::GeneratorError
+
+module JSON
+  def self.create_fast_state(); end
+
+  def self.create_pretty_state(); end
+
+  def self.load_file(filespec, opts=T.unsafe(nil)); end
+
+  def self.load_file!(filespec, opts=T.unsafe(nil)); end
+end
+
 class JSONSchemer::Result
   def self.keyword_init?(); end
 end
@@ -6353,7 +6383,13 @@ Net::HTTPServerErrorCode = Net::HTTPServerError
 
 Net::HTTPSession = Net::HTTP
 
-Net::HTTPSuccessCode = Net::HTTPSuccess
+class Net::HTTPSuccess
+end
+
+Net::HTTPSuccessCode::EXCEPTION_TYPE = Net::HTTPError
+
+class Net::HTTPSuccess
+end
 
 class Net::HTTPURITooLong
   HAS_BODY = ::T.let(nil, ::T.untyped)
@@ -9438,12 +9474,6 @@ module Reline
   VERSION = ::T.let(nil, ::T.untyped)
 end
 
-class Reline::ANSI
-  CAPNAME_KEY_BINDINGS = ::T.let(nil, ::T.untyped)
-  END_BRACKETED_PASTE = ::T.let(nil, ::T.untyped)
-  START_BRACKETED_PASTE = ::T.let(nil, ::T.untyped)
-end
-
 class Reline::Config
   KEYSEQ_PATTERN = ::T.let(nil, ::T.untyped)
   VARIABLE_NAMES = ::T.let(nil, ::T.untyped)
@@ -9454,7 +9484,7 @@ class Reline::Core
   ATTR_READER_NAMES = ::T.let(nil, ::T.untyped)
 end
 
-Reline::IOGate = Reline::ANSI
+Reline::IOGate = Reline::GeneralIO
 
 Reline::Key = Struct::Key
 
diff --git a/Library/Homebrew/standalone/init.rb b/Library/Homebrew/standalone/init.rb
index 709fd4251a..8729fa58c4 100644
--- a/Library/Homebrew/standalone/init.rb
+++ b/Library/Homebrew/standalone/init.rb
@@ -40,4 +40,9 @@ $LOAD_PATH.push HOMEBREW_LIBRARY_PATH.to_s unless $LOAD_PATH.include?(HOMEBREW_L
 require_relative "../vendor/bundle/bundler/setup"
 $LOAD_PATH.unshift "#{HOMEBREW_LIBRARY_PATH}/vendor/bundle/#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/" \
                    "bundler-#{Homebrew::HOMEBREW_BUNDLER_VERSION}/lib"
+if ruby_major == 2 && ruby_minor == 6
+  # TEMP: Ruby 3 transition
+  $LOAD_PATH.unshift "#{HOMEBREW_LIBRARY_PATH}/vendor/bundle/#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/" \
+                     "did_you_mean-1.6.3/lib"
+end
 $LOAD_PATH.uniq!
diff --git a/Library/Homebrew/vendor/bundle/bundler/setup.rb b/Library/Homebrew/vendor/bundle/bundler/setup.rb
index 3538db2495..2d511a8cc0 100644
--- a/Library/Homebrew/vendor/bundle/bundler/setup.rb
+++ b/Library/Homebrew/vendor/bundle/bundler/setup.rb
@@ -37,26 +37,25 @@ $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/addressable-2.8.5/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/ast-2.4.2/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/bindata-2.4.15/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/universal-darwin-22/#{Gem.extension_api_version}/msgpack-1.7.2")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/x86_64-darwin-15/#{Gem.extension_api_version}/msgpack-1.7.2")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/msgpack-1.7.2/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/universal-darwin-22/#{Gem.extension_api_version}/bootsnap-1.17.0")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/x86_64-darwin-15/#{Gem.extension_api_version}/bootsnap-1.17.0")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/bootsnap-1.17.0/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/universal-darwin-22/#{Gem.extension_api_version}/byebug-11.1.3")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/x86_64-darwin-15/#{Gem.extension_api_version}/byebug-11.1.3")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/byebug-11.1.3/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/coderay-1.1.3/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/highline-2.0.3/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/commander-4.6.0/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/did_you_mean-1.6.3/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/diff-lcs-1.5.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/docile-1.4.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/elftools-1.2.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/hana-1.3.7/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/universal-darwin-22/#{Gem.extension_api_version}/hpricot-0.8.6")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/x86_64-darwin-15/#{Gem.extension_api_version}/hpricot-0.8.6")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/hpricot-0.8.6/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/universal-darwin-22/#{Gem.extension_api_version}/json-2.6.3")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/json-2.6.3/lib")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/x86_64-darwin-15/#{Gem.extension_api_version}/json-2.7.0")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/json-2.7.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/regexp_parser-2.8.2/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/universal-darwin-22/#{Gem.extension_api_version}/unf_ext-0.0.9.1")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/x86_64-darwin-15/#{Gem.extension_api_version}/unf_ext-0.0.9.1")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/unf_ext-0.0.9.1/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/unf-0.1.4/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/simpleidn-0.2.1/lib")
@@ -65,7 +64,7 @@ $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/mustache-1.1.1/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/parallel-1.23.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/parallel_tests-3.13.0/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/universal-darwin-22/#{Gem.extension_api_version}/racc-1.7.3")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/x86_64-darwin-15/#{Gem.extension_api_version}/racc-1.7.3")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/racc-1.7.3/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/parser-3.2.2.4/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rainbow-3.1.1/lib")
@@ -77,7 +76,7 @@ $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rack-3.0.8/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/unparser-0.6.4/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rbi-0.0.14/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/universal-darwin-22/#{Gem.extension_api_version}/rdiscount-2.2.7.1")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/x86_64-darwin-15/#{Gem.extension_api_version}/rdiscount-2.2.7.1")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rdiscount-2.2.7.1/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rexml-3.2.6/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/ronn-0.7.3/lib")
@@ -101,18 +100,18 @@ $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rubocop-rspec-2.20.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/rubocop-sorbet-0.7.5/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/ruby-macho-4.0.0/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/universal-darwin-22/#{Gem.extension_api_version}/ruby-prof-1.4.3")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/x86_64-darwin-15/#{Gem.extension_api_version}/ruby-prof-1.4.3")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/ruby-prof-1.4.3/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/simplecov-html-0.12.3/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/simplecov_json_formatter-0.1.4/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/simplecov-0.22.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/simplecov-cobertura-2.1.0/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/sorbet-static-0.5.10461-universal-darwin-22/lib")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/sorbet-static-0.5.10461-universal-darwin-15/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/sorbet-0.5.10461/lib")
 $:.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-1.3.0/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-22/#{Gem.extension_api_version}/stackprof-0.2.25")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/x86_64-darwin-15/#{Gem.extension_api_version}/stackprof-0.2.25")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/stackprof-0.2.25/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/yard-0.9.34/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/yard-sorbet-0.6.1/lib")