diff --git a/Library/Homebrew/.ruby-version b/Library/Homebrew/.ruby-version
index 4772543317..619b537668 100644
--- a/Library/Homebrew/.ruby-version
+++ b/Library/Homebrew/.ruby-version
@@ -1 +1 @@
-3.3.2
+3.3.3
diff --git a/Library/Homebrew/Gemfile.lock b/Library/Homebrew/Gemfile.lock
index 3c0034ea74..ecd4a05a9d 100644
--- a/Library/Homebrew/Gemfile.lock
+++ b/Library/Homebrew/Gemfile.lock
@@ -197,7 +197,7 @@ DEPENDENCIES
   yard-sorbet
 
 RUBY VERSION
-   ruby 3.3.2p78
+   ruby 3.3.3p89
 
 BUNDLED WITH
-   2.5.9
+   2.5.11
diff --git a/Library/Homebrew/cmd/vendor-install.sh b/Library/Homebrew/cmd/vendor-install.sh
index d173754175..67240ef964 100644
--- a/Library/Homebrew/cmd/vendor-install.sh
+++ b/Library/Homebrew/cmd/vendor-install.sh
@@ -21,19 +21,19 @@ set_ruby_variables() {
        # use a x86_64 Portable Ruby.
        [[ "${VENDOR_PHYSICAL_PROCESSOR}" == "arm64" && "${HOMEBREW_PREFIX}" == "/usr/local" ]]
     then
-      ruby_FILENAME="portable-ruby-3.3.2.el_capitan.bottle.tar.gz"
-      ruby_SHA="5c86a23e0e3caee1a4cfd958ed7d50a38e752ebaf2e7c5717e5c8eabaa6e9f12"
+      ruby_FILENAME="portable-ruby-3.3.3.el_capitan.bottle.tar.gz"
+      ruby_SHA="a5ef040e054444a0eb2cbcc1032fed14702dfbe2e55b25e609f3ce643f23c4ee"
     elif [[ "${VENDOR_PHYSICAL_PROCESSOR}" == "arm64" ]]
     then
-      ruby_FILENAME="portable-ruby-3.3.2.arm64_big_sur.bottle.tar.gz"
-      ruby_SHA="bbb73a9d86fa37128c54c74b020096a646c46c525fd5eb0c4a2467551fb2d377"
+      ruby_FILENAME="portable-ruby-3.3.3.arm64_big_sur.bottle.tar.gz"
+      ruby_SHA="49847c7a13f7094b211f6d0025900dd23716be07dac894a3d6941d7696296306"
     fi
   elif [[ -n "${HOMEBREW_LINUX}" ]]
   then
     case "${VENDOR_PROCESSOR}" in
       x86_64)
-        ruby_FILENAME="portable-ruby-3.3.2.x86_64_linux.bottle.tar.gz"
-        ruby_SHA="dd3cffcc524de404e87bef92d89f3694a9ef13f2586a6dce4807456f1b30c7b0"
+        ruby_FILENAME="portable-ruby-3.3.3.x86_64_linux.bottle.tar.gz"
+        ruby_SHA="40a1dbc25bb1a8bbdf0bba53d3f16c45416be12d4c6d48b4530f90b2a77d64ce"
         ;;
       *) ;;
     esac
diff --git a/Library/Homebrew/standalone/init.rb b/Library/Homebrew/standalone/init.rb
index 5d673bf8ef..dc2ad59894 100644
--- a/Library/Homebrew/standalone/init.rb
+++ b/Library/Homebrew/standalone/init.rb
@@ -29,6 +29,7 @@ $LOAD_PATH.reject! { |path| path.start_with?(RbConfig::CONFIG["sitedir"]) }
 require "pathname"
 dir = __dir__ || raise("__dir__ is not defined")
 HOMEBREW_LIBRARY_PATH = Pathname(dir).parent.realpath.freeze
+HOMEBREW_PORTABLE_RUBY = Pathname.new(RbConfig.ruby).to_s.include?("/vendor/portable-ruby/").freeze
 
 require_relative "../utils/gems"
 Homebrew.setup_gem_environment!(setup_path: false)
@@ -39,14 +40,6 @@ if !gems_vendored && !ENV["HOMEBREW_SKIP_INITIAL_GEM_INSTALL"]
   ENV["HOMEBREW_SKIP_INITIAL_GEM_INSTALL"] = "1"
 end
 
-if Pathname.new(RbConfig.ruby).to_s.include?("/vendor/portable-ruby/")
-  ruby_version = RbConfig::CONFIG["ruby_version"]
-  ruby_path = "#{RbConfig::CONFIG["rubylibprefix"]}/gems/#{ruby_version}"
-
-  $LOAD_PATH.unshift "#{ruby_path}/extensions/#{Gem::Platform.local}/#{ruby_version}-static/debug-1.9.1"
-  $LOAD_PATH.unshift "#{ruby_path}/gems/debug-1.9.1/lib"
-end
-
 unless $LOAD_PATH.include?(HOMEBREW_LIBRARY_PATH.to_s)
   # Insert the path after any existing Homebrew paths (e.g. those inserted by tests and parent processes)
   last_homebrew_path_idx = $LOAD_PATH.rindex do |path|
@@ -55,6 +48,7 @@ unless $LOAD_PATH.include?(HOMEBREW_LIBRARY_PATH.to_s)
   $LOAD_PATH.insert(last_homebrew_path_idx + 1, HOMEBREW_LIBRARY_PATH.to_s)
 end
 require_relative "../vendor/bundle/bundler/setup"
+require "portable_ruby_gems" if HOMEBREW_PORTABLE_RUBY
 $LOAD_PATH.unshift "#{HOMEBREW_LIBRARY_PATH}/vendor/bundle/#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/" \
                    "bundler-#{Homebrew::HOMEBREW_BUNDLER_VERSION}/lib"
 $LOAD_PATH.uniq!
diff --git a/Library/Homebrew/startup/bootsnap.rb b/Library/Homebrew/startup/bootsnap.rb
index d7faddb3b7..19511b71e5 100644
--- a/Library/Homebrew/startup/bootsnap.rb
+++ b/Library/Homebrew/startup/bootsnap.rb
@@ -14,7 +14,7 @@ if homebrew_bootsnap_enabled
   begin
     require "bootsnap"
   rescue LoadError
-    raise if ENV["HOMEBREW_BOOTSNAP_RETRY"]
+    raise if ENV["HOMEBREW_BOOTSNAP_RETRY"] || HOMEBREW_PORTABLE_RUBY
 
     Homebrew.install_bundler_gems!(groups: ["bootsnap"], only_warn_on_failure: true)
 
diff --git a/Library/Homebrew/test/sorbet/tapioca/config_spec.rb b/Library/Homebrew/test/sorbet/tapioca/config_spec.rb
index 3fb5101618..bb37b78ad8 100644
--- a/Library/Homebrew/test/sorbet/tapioca/config_spec.rb
+++ b/Library/Homebrew/test/sorbet/tapioca/config_spec.rb
@@ -1,6 +1,6 @@
 # frozen_string_literal: true
 
-require "rubygems"
+require "bundler"
 require "yaml"
 
 RSpec.describe "Tapioca Config", type: :system do
@@ -8,7 +8,11 @@ RSpec.describe "Tapioca Config", type: :system do
 
   it "only excludes dependencies" do
     exclusions = config.dig("gem", "exclude")
-    dependencies = Gem::Specification.all.map(&:name)
+    dependencies = Bundler::Definition.build(
+      HOMEBREW_LIBRARY_PATH/"Gemfile",
+      HOMEBREW_LIBRARY_PATH/"Gemfile.lock",
+      false,
+    ).resolve.names
     expect(exclusions - dependencies).to be_empty
   end
 end
diff --git a/Library/Homebrew/utils/gems.rb b/Library/Homebrew/utils/gems.rb
index 6766db8b56..db35ff5d61 100644
--- a/Library/Homebrew/utils/gems.rb
+++ b/Library/Homebrew/utils/gems.rb
@@ -10,7 +10,7 @@ require "English"
 module Homebrew
   # Keep in sync with the `Gemfile.lock`'s BUNDLED WITH.
   # After updating this, run `brew vendor-gems --update=--bundler`.
-  HOMEBREW_BUNDLER_VERSION = "2.5.9"
+  HOMEBREW_BUNDLER_VERSION = "2.5.11"
 
   # Bump this whenever a committed vendored gem is later added to or exclusion removed from gitignore.
   # This will trigger it to reinstall properly if `brew install-bundler-gems` needs it.
@@ -241,6 +241,7 @@ module Homebrew
 
     # Combine the passed groups with the ones stored in settings.
     groups |= (user_gem_groups & valid_gem_groups)
+    groups.delete("bootsnap") if HOMEBREW_PORTABLE_RUBY
     groups.sort!
 
     if (homebrew_bundle_user_cache = ENV.fetch("HOMEBREW_BUNDLE_USER_CACHE", nil))
diff --git a/Library/Homebrew/vendor/portable-ruby-version b/Library/Homebrew/vendor/portable-ruby-version
index 4772543317..619b537668 100644
--- a/Library/Homebrew/vendor/portable-ruby-version
+++ b/Library/Homebrew/vendor/portable-ruby-version
@@ -1 +1 @@
-3.3.2
+3.3.3
diff --git a/docs/.ruby-version b/docs/.ruby-version
index 4772543317..619b537668 100644
--- a/docs/.ruby-version
+++ b/docs/.ruby-version
@@ -1 +1 @@
-3.3.2
+3.3.3