diff --git a/Library/Homebrew/homebrew_bootsnap.rb b/Library/Homebrew/homebrew_bootsnap.rb
index 680acc90b8..c4d1ce33a3 100644
--- a/Library/Homebrew/homebrew_bootsnap.rb
+++ b/Library/Homebrew/homebrew_bootsnap.rb
@@ -1,24 +1,22 @@
 # typed: false
 # frozen_string_literal: true
 
-homebrew_bootsnap_enabled = !ENV["HOMEBREW_NO_BOOTSNAP"] &&
-                            ENV["HOMEBREW_BOOTSNAP"] &&
-                            # portable ruby doesn't play nice with bootsnap
-                            !ENV["HOMEBREW_FORCE_VENDOR_RUBY"] &&
-                            (!ENV["HOMEBREW_MACOS_VERSION"] || ENV["HOMEBREW_MACOS_SYSTEM_RUBY_NEW_ENOUGH"]) &&
-                            # Apple Silicon doesn't play nice with bootsnap
-                            (ENV["HOMEBREW_PROCESSOR"] == "Intel")
+homebrew_bootsnap_enabled = !ENV["HOMEBREW_NO_BOOTSNAP"] && ENV["HOMEBREW_BOOTSNAP"]
 
-# we need some development tools to build bootsnap native code
-development_tools_installed = if !homebrew_bootsnap_enabled
-  false
-elsif RbConfig::CONFIG["host_os"].include? "darwin"
-  File.directory?("/Applications/Xcode.app") || File.directory?("/Library/Developer/CommandLineTools")
+# portable ruby doesn't play nice with bootsnap
+# Can't use .exclude? here because we haven't required active_support yet.
+homebrew_bootsnap_enabled &&= !ENV["HOMEBREW_RUBY_PATH"].to_s.include?("/vendor/portable-ruby/") # rubocop:disable Rails/NegateInclude
+
+homebrew_bootsnap_enabled &&= if ENV["HOMEBREW_MACOS_VERSION"]
+  # Apple Silicon doesn't play nice with bootsnap
+  ENV["HOMEBREW_PROCESSOR"] == "Intel" &&
+    # we need some development tools to build bootsnap native code
+    (File.directory?("/Applications/Xcode.app") || File.directory?("/Library/Developer/CommandLineTools"))
 else
   File.executable?("/usr/bin/clang") || File.executable?("/usr/bin/gcc")
 end
 
-if homebrew_bootsnap_enabled && development_tools_installed
+if homebrew_bootsnap_enabled
   require "rubygems"
 
   begin
@@ -26,7 +24,7 @@ if homebrew_bootsnap_enabled && development_tools_installed
   rescue LoadError
     unless ENV["HOMEBREW_BOOTSNAP_RETRY"]
       require "utils/gems"
-      Homebrew.install_bundler_gems!
+      Homebrew.install_bundler_gems!(only_warn_on_failure: true)
 
       ENV["HOMEBREW_BOOTSNAP_RETRY"] = "1"
       exec ENV["HOMEBREW_BREW_FILE"], *ARGV
diff --git a/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi b/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi
index bb2b3e931a..96a9d348fd 100644
--- a/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi
+++ b/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi
@@ -532,6 +532,14 @@ class ActiveSupport::CurrentAttributes
   def _reset_callbacks(); end
 
   def _run_reset_callbacks(&block); end
+
+  def attributes(); end
+
+  def attributes=(attributes); end
+
+  def reset(); end
+
+  def set(set_attributes); end
 end
 
 class ActiveSupport::CurrentAttributes
@@ -553,9 +561,17 @@ class ActiveSupport::CurrentAttributes
 
   def self.before_reset(&block); end
 
+  def self.clear_all(); end
+
   def self.instance(); end
 
+  def self.reset(*args, &block); end
+
+  def self.reset_all(); end
+
   def self.resets(&block); end
+
+  def self.set(*args, &block); end
 end
 
 module ActiveSupport::Dependencies
@@ -2814,12 +2830,99 @@ end
 class Bootsnap::CompileCache::Error
 end
 
+module Bootsnap::CompileCache::ISeq
+end
+
+module Bootsnap::CompileCache::ISeq::InstructionSequenceMixin
+  def compile_option=(hash); end
+
+  def load_iseq(path); end
+end
+
+module Bootsnap::CompileCache::ISeq::InstructionSequenceMixin
+end
+
+module Bootsnap::CompileCache::ISeq
+  def self.cache_dir(); end
+
+  def self.cache_dir=(cache_dir); end
+
+  def self.compile_option_updated(); end
+
+  def self.fetch(path, cache_dir: T.unsafe(nil)); end
+
+  def self.input_to_output(_data, _kwargs); end
+
+  def self.input_to_storage(_, path); end
+
+  def self.install!(cache_dir); end
+
+  def self.precompile(path, cache_dir: T.unsafe(nil)); end
+
+  def self.storage_to_output(binary, _args); end
+end
+
+module Bootsnap::CompileCache::Native
+end
+
+module Bootsnap::CompileCache::Native
+  def self.compile_option_crc32=(compile_option_crc32); end
+
+  def self.coverage_running?(); end
+
+  def self.fetch(_, _1, _2, _3); end
+
+  def self.precompile(_, _1, _2); end
+end
+
 class Bootsnap::CompileCache::PermissionError
 end
 
 class Bootsnap::CompileCache::PermissionError
 end
 
+class Bootsnap::CompileCache::Uncompilable
+end
+
+class Bootsnap::CompileCache::Uncompilable
+end
+
+module Bootsnap::CompileCache::YAML
+end
+
+module Bootsnap::CompileCache::YAML::Patch
+  def load_file(path, *args); end
+end
+
+module Bootsnap::CompileCache::YAML::Patch
+end
+
+module Bootsnap::CompileCache::YAML
+  def self.cache_dir(); end
+
+  def self.cache_dir=(cache_dir); end
+
+  def self.init!(); end
+
+  def self.input_to_output(data, kwargs); end
+
+  def self.input_to_storage(contents, _); end
+
+  def self.install!(cache_dir); end
+
+  def self.msgpack_factory(); end
+
+  def self.msgpack_factory=(msgpack_factory); end
+
+  def self.precompile(path, cache_dir: T.unsafe(nil)); end
+
+  def self.storage_to_output(data, kwargs); end
+
+  def self.supported_options(); end
+
+  def self.supported_options=(supported_options); end
+end
+
 module Bootsnap::CompileCache
   def self.permission_error(path); end
 
@@ -2950,6 +3053,13 @@ module Bootsnap::LoadPathCache::ChangeObserver
   def self.register(observer, arr); end
 end
 
+module Bootsnap::LoadPathCache::CoreExt
+end
+
+module Bootsnap::LoadPathCache::CoreExt
+  def self.make_load_error(path); end
+end
+
 class Bootsnap::LoadPathCache::FallbackScan
 end
 
@@ -5574,6 +5684,15 @@ module Cask::Caskroom
   extend ::T::Private::Methods::SingletonMethodHooks
 end
 
+class Cask::Cmd::AbstractCommand
+  include ::Homebrew::Search::Extension
+end
+
+class Cask::Cmd::AbstractCommand
+  extend ::T::Private::Methods::MethodHooks
+  extend ::T::Private::Methods::SingletonMethodHooks
+end
+
 class Cask::Config
   def appdir(); end
 
@@ -7021,8 +7140,6 @@ end
 class Errno::EBADRPC
 end
 
-Errno::ECAPMODE = Errno::NOERROR
-
 Errno::EDEADLOCK = Errno::NOERROR
 
 class Errno::EDEVERR
@@ -7043,13 +7160,6 @@ end
 
 Errno::EIPSEC = Errno::NOERROR
 
-class Errno::ELAST
-  Errno = ::T.let(nil, ::T.untyped)
-end
-
-class Errno::ELAST
-end
-
 class Errno::ENEEDAUTH
   Errno = ::T.let(nil, ::T.untyped)
 end
@@ -7071,8 +7181,6 @@ end
 class Errno::ENOPOLICY
 end
 
-Errno::ENOTCAPABLE = Errno::NOERROR
-
 class Errno::ENOTSUP
   Errno = ::T.let(nil, ::T.untyped)
 end
@@ -7115,7 +7223,12 @@ end
 class Errno::EPWROFF
 end
 
-Errno::EQFULL = Errno::ELAST
+class Errno::EQFULL
+  Errno = ::T.let(nil, ::T.untyped)
+end
+
+class Errno::EQFULL
+end
 
 class Errno::ERPCMISMATCH
   Errno = ::T.let(nil, ::T.untyped)
@@ -8251,6 +8364,14 @@ module Homebrew::Livecheck
   extend ::T::Private::Methods::SingletonMethodHooks
 end
 
+module Homebrew::MissingFormula
+  extend ::T::Private::Methods::SingletonMethodHooks
+end
+
+module Homebrew::Search
+  include ::Homebrew::Search::Extension
+end
+
 module Homebrew::Settings
   extend ::T::Private::Methods::MethodHooks
   extend ::T::Private::Methods::SingletonMethodHooks
@@ -9607,11 +9728,13 @@ module Kernel
   extend ::T::Private::Methods::SingletonMethodHooks
   def self.at_exit(); end
 
+  def self.autoload(_, _1); end
+
   def self.fork(); end
 
   def self.gem(dep, *reqs); end
 
-  def self.load(*_); end
+  def self.load(path, wrap=T.unsafe(nil)); end
 
   def self.require(path); end
 end
@@ -11921,6 +12044,8 @@ class Module
 
   def anonymous?(); end
 
+  def autoload_without_bootsnap(_, _1); end
+
   def context(*a, &b); end
 
   def deprecate(*method_names); end
@@ -12275,13 +12400,9 @@ end
 
 Net::HTTPFatalErrorCode = Net::HTTPClientError
 
-class Net::HTTPInformation
-end
+Net::HTTPInformation::EXCEPTION_TYPE = Net::HTTPError
 
-Net::HTTPInformationCode::EXCEPTION_TYPE = Net::HTTPError
-
-class Net::HTTPInformation
-end
+Net::HTTPInformationCode = Net::HTTPInformation
 
 class Net::HTTPLoopDetected
   HAS_BODY = ::T.let(nil, ::T.untyped)
@@ -12345,13 +12466,9 @@ Net::HTTPServerErrorCode = Net::HTTPServerError
 
 Net::HTTPSession = Net::HTTP
 
-class Net::HTTPSuccess
-end
+Net::HTTPSuccess::EXCEPTION_TYPE = Net::HTTPError
 
-Net::HTTPSuccessCode::EXCEPTION_TYPE = Net::HTTPError
-
-class Net::HTTPSuccess
-end
+Net::HTTPSuccessCode = Net::HTTPSuccess
 
 class Net::HTTPURITooLong
   HAS_BODY = ::T.let(nil, ::T.untyped)
@@ -12521,6 +12638,7 @@ class Object
   def to_query(key); end
 
   def to_yaml(options=T.unsafe(nil)); end
+  APPLE_GEM_HOME = ::T.let(nil, ::T.untyped)
   ARGF = ::T.let(nil, ::T.untyped)
   ARGV = ::T.let(nil, ::T.untyped)
   BUG_REPORTS_URL = ::T.let(nil, ::T.untyped)
@@ -12585,6 +12703,8 @@ class Object
   RUBY_DESCRIPTION = ::T.let(nil, ::T.untyped)
   RUBY_ENGINE = ::T.let(nil, ::T.untyped)
   RUBY_ENGINE_VERSION = ::T.let(nil, ::T.untyped)
+  RUBY_FRAMEWORK = ::T.let(nil, ::T.untyped)
+  RUBY_FRAMEWORK_VERSION = ::T.let(nil, ::T.untyped)
   RUBY_PATCHLEVEL = ::T.let(nil, ::T.untyped)
   RUBY_PATH = ::T.let(nil, ::T.untyped)
   RUBY_PLATFORM = ::T.let(nil, ::T.untyped)
@@ -12637,11 +12757,7 @@ class OpenSSL::KDF::KDFError
 end
 
 module OpenSSL::KDF
-  def self.hkdf(*_); end
-
   def self.pbkdf2_hmac(*_); end
-
-  def self.scrypt(*_); end
 end
 
 class OpenSSL::OCSP::Request
@@ -12650,29 +12766,20 @@ end
 
 OpenSSL::PKCS7::Signer = OpenSSL::PKCS7::SignerInfo
 
-class OpenSSL::PKey::EC
-  EXPLICIT_CURVE = ::T.let(nil, ::T.untyped)
-end
-
 class OpenSSL::PKey::EC::Point
   def to_octet_string(_); end
 end
 
 module OpenSSL::SSL
-  OP_ALLOW_NO_DHE_KEX = ::T.let(nil, ::T.untyped)
   OP_ALLOW_UNSAFE_LEGACY_RENEGOTIATION = ::T.let(nil, ::T.untyped)
   OP_CRYPTOPRO_TLSEXT_BUG = ::T.let(nil, ::T.untyped)
   OP_LEGACY_SERVER_CONNECT = ::T.let(nil, ::T.untyped)
-  OP_NO_ENCRYPT_THEN_MAC = ::T.let(nil, ::T.untyped)
-  OP_NO_RENEGOTIATION = ::T.let(nil, ::T.untyped)
-  OP_NO_TLSv1_3 = ::T.let(nil, ::T.untyped)
   OP_SAFARI_ECDHE_ECDSA_BUG = ::T.let(nil, ::T.untyped)
   OP_TLSEXT_PADDING = ::T.let(nil, ::T.untyped)
   SSL2_VERSION = ::T.let(nil, ::T.untyped)
   SSL3_VERSION = ::T.let(nil, ::T.untyped)
   TLS1_1_VERSION = ::T.let(nil, ::T.untyped)
   TLS1_2_VERSION = ::T.let(nil, ::T.untyped)
-  TLS1_3_VERSION = ::T.let(nil, ::T.untyped)
   TLS1_VERSION = ::T.let(nil, ::T.untyped)
 end
 
@@ -17084,6 +17191,7 @@ module Psych
 end
 
 module Psych
+  extend ::Bootsnap::CompileCache::YAML::Patch
   def self.add_builtin_type(type_tag, &block); end
 
   def self.add_domain_type(domain, type_tag, &block); end
@@ -27855,6 +27963,10 @@ class RubyVM::AbstractSyntaxTree::Node
   def pretty_print_children(q, names=T.unsafe(nil)); end
 end
 
+class RubyVM::InstructionSequence
+  extend ::Bootsnap::CompileCache::ISeq::InstructionSequenceMixin
+end
+
 module RubyVM::MJIT
 end
 
@@ -28744,6 +28856,7 @@ class Socket
   IPV6_PATHMTU = ::T.let(nil, ::T.untyped)
   IPV6_RECVPATHMTU = ::T.let(nil, ::T.untyped)
   IPV6_USE_MIN_MTU = ::T.let(nil, ::T.untyped)
+  IP_DONTFRAG = ::T.let(nil, ::T.untyped)
   IP_PORTRANGE = ::T.let(nil, ::T.untyped)
   IP_RECVDSTADDR = ::T.let(nil, ::T.untyped)
   IP_RECVIF = ::T.let(nil, ::T.untyped)
@@ -28835,6 +28948,7 @@ module Socket::Constants
   IPV6_PATHMTU = ::T.let(nil, ::T.untyped)
   IPV6_RECVPATHMTU = ::T.let(nil, ::T.untyped)
   IPV6_USE_MIN_MTU = ::T.let(nil, ::T.untyped)
+  IP_DONTFRAG = ::T.let(nil, ::T.untyped)
   IP_PORTRANGE = ::T.let(nil, ::T.untyped)
   IP_RECVDSTADDR = ::T.let(nil, ::T.untyped)
   IP_RECVIF = ::T.let(nil, ::T.untyped)
diff --git a/Library/Homebrew/utils/gems.rb b/Library/Homebrew/utils/gems.rb
index a75f0b8561..b19eb36cb3 100644
--- a/Library/Homebrew/utils/gems.rb
+++ b/Library/Homebrew/utils/gems.rb
@@ -34,6 +34,14 @@ module Homebrew
     end
   end
 
+  def opoo_if_defined(message)
+    if defined?(opoo)
+      $stderr.opoo message
+    else
+      $stderr.puts "Warning: #{message}"
+    end
+  end
+
   def odie_if_defined(message)
     if defined?(odie)
       odie message
@@ -105,7 +113,7 @@ module Homebrew
     )
   end
 
-  def install_bundler_gems!
+  def install_bundler_gems!(only_warn_on_failure: false)
     install_bundler!
 
     ENV["BUNDLE_GEMFILE"] = File.join(ENV.fetch("HOMEBREW_LIBRARY"), "Homebrew", "Gemfile")
@@ -117,9 +125,14 @@ module Homebrew
       # for some reason sometimes the exit code lies so check the output too.
       if bundle_check_failed || bundle_check_output.include?("Install missing gems")
         unless system bundle, "install"
-          odie_if_defined <<~EOS
+          message = <<~EOS
             failed to run `#{bundle} install`!
           EOS
+          if only_warn_on_failure
+            opoo_if_defined message
+          else
+            odie_if_defined message
+          end
         end
       else
         true
diff --git a/Library/Homebrew/utils/gems.rbi b/Library/Homebrew/utils/gems.rbi
index 47c3ced643..0aad665138 100644
--- a/Library/Homebrew/utils/gems.rbi
+++ b/Library/Homebrew/utils/gems.rbi
@@ -22,6 +22,6 @@ module Homebrew
   sig { void }
   def install_bundler!; end
 
-  sig { void }
-  def install_bundler_gems!; end
+  sig { params(only_warn_on_failure: T::Boolean).void }
+  def install_bundler_gems!(only_warn_on_failure: false); end
 end