diff --git a/Library/Homebrew/Gemfile.lock b/Library/Homebrew/Gemfile.lock
index 518ba1d5ed..61febf66ff 100644
--- a/Library/Homebrew/Gemfile.lock
+++ b/Library/Homebrew/Gemfile.lock
@@ -124,14 +124,14 @@ GEM
       rspec (>= 3, < 4)
     rspec_junit_formatter (0.5.1)
       rspec-core (>= 2, < 4, != 2.12.0)
-    rubocop (1.33.0)
+    rubocop (1.34.1)
       json (~> 2.3)
       parallel (~> 1.10)
-      parser (>= 3.1.0.0)
+      parser (>= 3.1.2.1)
       rainbow (>= 2.2.2, < 4.0)
       regexp_parser (>= 1.8, < 3.0)
       rexml (>= 3.2.5, < 4.0)
-      rubocop-ast (>= 1.19.1, < 2.0)
+      rubocop-ast (>= 1.20.0, < 2.0)
       ruby-progressbar (~> 1.7)
       unicode-display_width (>= 1.4.0, < 3.0)
     rubocop-ast (1.21.0)
diff --git a/Library/Homebrew/dev-cmd/bump-cask-pr.rb b/Library/Homebrew/dev-cmd/bump-cask-pr.rb
index d6b1586e0b..cc33184b1a 100644
--- a/Library/Homebrew/dev-cmd/bump-cask-pr.rb
+++ b/Library/Homebrew/dev-cmd/bump-cask-pr.rb
@@ -156,11 +156,11 @@ module Homebrew
     end
 
     if new_hash.present? && cask.language.blank? # avoid repeated replacement for multilanguage cask
-      hash_regex = old_hash == :no_check ? ":no_check" : "[\"']#{Regexp.escape(old_hash.to_s)}[\"']"
+      hash_regex = (old_hash == :no_check) ? ":no_check" : "[\"']#{Regexp.escape(old_hash.to_s)}[\"']"
 
       replacement_pairs << [
         /sha256\s+#{hash_regex}/m,
-        "sha256 #{new_hash == :no_check ? ":no_check" : "\"#{new_hash}\""}",
+        "sha256 #{(new_hash == :no_check) ? ":no_check" : "\"#{new_hash}\""}",
       ]
     end
 
diff --git a/Library/Homebrew/dev-cmd/rubocop.sh b/Library/Homebrew/dev-cmd/rubocop.sh
index bc1b8ca769..28e9df7a42 100644
--- a/Library/Homebrew/dev-cmd/rubocop.sh
+++ b/Library/Homebrew/dev-cmd/rubocop.sh
@@ -13,13 +13,16 @@ homebrew-rubocop() {
 
   GEM_VERSION="$("${HOMEBREW_RUBY_PATH}" "${RUBY_DISABLE_OPTIONS}" -rrbconfig -e 'puts RbConfig::CONFIG["ruby_version"]')"
   GEM_HOME="${HOMEBREW_LIBRARY}/Homebrew/vendor/bundle/ruby/${GEM_VERSION}"
+  BUNDLE_GEMFILE="${HOMEBREW_LIBRARY}/Homebrew/Gemfile"
 
-  if ! [[ -f "${GEM_HOME}/bin/rubocop" ]]
+  export GEM_HOME
+  export BUNDLE_GEMFILE
+
+  if ! bundle check &>/dev/null
   then
     "${HOMEBREW_BREW_FILE}" install-bundler-gems
   fi
 
-  export GEM_HOME
   export PATH="${GEM_HOME}/bin:${PATH}"
 
   RUBOCOP="${HOMEBREW_LIBRARY}/Homebrew/utils/rubocop.rb"
diff --git a/Library/Homebrew/extend/on_system.rb b/Library/Homebrew/extend/on_system.rb
index 8ba6415b99..035940ba0b 100644
--- a/Library/Homebrew/extend/on_system.rb
+++ b/Library/Homebrew/extend/on_system.rb
@@ -66,7 +66,7 @@ module OnSystem
       end
     end
 
-    base.define_method(:on_arch_conditional) do |arm:, intel:|
+    base.define_method(:on_arch_conditional) do |arm: nil, intel: nil|
       @on_system_blocks_exist = true
 
       return arm if OnSystem.arch_condition_met? :arm
diff --git a/Library/Homebrew/extend/os/linux/extend/ENV/super.rb b/Library/Homebrew/extend/os/linux/extend/ENV/super.rb
index 8dd6f95c8d..eb2460a5ba 100644
--- a/Library/Homebrew/extend/os/linux/extend/ENV/super.rb
+++ b/Library/Homebrew/extend/os/linux/extend/ENV/super.rb
@@ -51,6 +51,7 @@ module Superenv
   def determine_rpath_paths(formula)
     PATH.new(
       *formula&.lib,
+      "#{HOMEBREW_PREFIX}/opt/gcc/lib/gcc/current",
       PATH.new(run_time_deps.map { |dep| dep.opt_lib.to_s }).existing,
       "#{HOMEBREW_PREFIX}/lib",
     )
diff --git a/Library/Homebrew/extend/os/linux/linkage_checker.rb b/Library/Homebrew/extend/os/linux/linkage_checker.rb
index 4e2bbf557b..e94995e966 100644
--- a/Library/Homebrew/extend/os/linux/linkage_checker.rb
+++ b/Library/Homebrew/extend/os/linux/linkage_checker.rb
@@ -72,6 +72,9 @@ class LinkageChecker
     @unwanted_system_dylibs = @system_dylibs.reject do |s|
       SYSTEM_LIBRARY_ALLOWLIST.include? File.basename(s)
     end
-    @undeclared_deps -= [CompilerSelector.preferred_gcc, "glibc"]
+    # FIXME: Remove this when these dependencies are injected correctly (e.g. through `DependencyCollector`)
+    # See discussion at
+    #   https://github.com/Homebrew/brew/pull/13577
+    @undeclared_deps -= [CompilerSelector.preferred_gcc, "glibc", "gcc"]
   end
 end
diff --git a/Library/Homebrew/rubocops/cask/constants/stanza.rb b/Library/Homebrew/rubocops/cask/constants/stanza.rb
index 959beda606..93a9b67d55 100644
--- a/Library/Homebrew/rubocops/cask/constants/stanza.rb
+++ b/Library/Homebrew/rubocops/cask/constants/stanza.rb
@@ -6,7 +6,7 @@ module RuboCop
     # Constants available globally for use in all cask cops.
     module Constants
       STANZA_GROUPS = [
-        [:version, :sha256, :arch],
+        [:version, :sha256],
         [:language],
         [:url, :appcast, :name, :desc, :homepage],
         [:livecheck],
diff --git a/Library/Homebrew/rubocops/lines.rb b/Library/Homebrew/rubocops/lines.rb
index e8c7a631a3..d8fd97bead 100644
--- a/Library/Homebrew/rubocops/lines.rb
+++ b/Library/Homebrew/rubocops/lines.rb
@@ -401,7 +401,7 @@ module RuboCop
           info[:if_module], info[:if_method] = if ON_ARCH_OPTIONS.include?(on_system_option)
             ["Hardware::CPU", :"#{on_system_option}?"]
           elsif ON_BASE_OS_OPTIONS.include?(on_system_option)
-            ["OS", on_system_option == :macos ? :mac? : :linux?]
+            ["OS", (on_system_option == :macos) ? :mac? : :linux?]
           else
             ["MacOS", :version]
           end
@@ -493,7 +493,7 @@ module RuboCop
                 else_info = if else_node.present?
                   {
                     can_autocorrect:  true,
-                    on_system_method: on_system_option == :intel ? "on_arm" : "on_intel",
+                    on_system_method: (on_system_option == :intel) ? "on_arm" : "on_intel",
                     node:             else_node,
                   }
                 end
@@ -505,7 +505,7 @@ module RuboCop
                 else_info = if else_node.present?
                   {
                     can_autocorrect:  true,
-                    on_system_method: on_system_option == :macos ? "on_linux" : "on_macos",
+                    on_system_method: (on_system_option == :macos) ? "on_linux" : "on_macos",
                     node:             else_node,
                   }
                 end
diff --git a/Library/Homebrew/service.rb b/Library/Homebrew/service.rb
index f40cff066f..3ef98c0792 100644
--- a/Library/Homebrew/service.rb
+++ b/Library/Homebrew/service.rb
@@ -405,7 +405,7 @@ module Homebrew
       cmd = command.join(" ")
 
       options = []
-      options << "Type=#{@launch_only_once == true ? "oneshot" : "simple"}"
+      options << "Type=#{(@launch_only_once == true) ? "oneshot" : "simple"}"
       options << "ExecStart=#{cmd}"
 
       options << "Restart=always" if @keep_alive.present? && @keep_alive[:always].present?
@@ -441,8 +441,8 @@ module Homebrew
       options << "OnUnitActiveSec=#{@interval}" if @run_type == RUN_TYPE_INTERVAL
 
       if @run_type == RUN_TYPE_CRON
-        minutes = @cron[:Minute] == "*" ? "*" : format("%02d", @cron[:Minute])
-        hours   = @cron[:Hour] == "*" ? "*" : format("%02d", @cron[:Hour])
+        minutes = (@cron[:Minute] == "*") ? "*" : format("%02d", @cron[:Minute])
+        hours   = (@cron[:Hour] == "*") ? "*" : format("%02d", @cron[:Hour])
         options << "OnCalendar=#{@cron[:Weekday]}-*-#{@cron[:Month]}-#{@cron[:Day]} #{hours}:#{minutes}:00"
       end
 
diff --git a/Library/Homebrew/software_spec.rb b/Library/Homebrew/software_spec.rb
index 0a246d3469..6b4c15981e 100644
--- a/Library/Homebrew/software_spec.rb
+++ b/Library/Homebrew/software_spec.rb
@@ -582,7 +582,7 @@ class BottleSpecification
     tags = collector.tags.sort_by do |tag|
       version = tag.to_macos_version
       # Give arm64 bottles a higher priority so they are first
-      priority = tag.arch == :arm64 ? "2" : "1"
+      priority = (tag.arch == :arm64) ? "2" : "1"
       "#{priority}.#{version}_#{tag}"
     rescue MacOSVersionError
       # Sort non-MacOS tags below MacOS tags.
diff --git a/Library/Homebrew/style.rb b/Library/Homebrew/style.rb
index 8b253c0f5f..ce38f1a1af 100644
--- a/Library/Homebrew/style.rb
+++ b/Library/Homebrew/style.rb
@@ -49,7 +49,7 @@ module Homebrew
                     .partition { |f| f.realpath == HOMEBREW_BREW_FILE.realpath || f.extname == ".sh" }
 
       rubocop_result = if shell_files.any? && ruby_files.none?
-        output_type == :json ? [] : true
+        (output_type == :json) ? [] : true
       else
         run_rubocop(ruby_files, output_type,
                     fix: fix,
@@ -60,7 +60,7 @@ module Homebrew
       end
 
       shellcheck_result = if ruby_files.any? && shell_files.none?
-        output_type == :json ? [] : true
+        (output_type == :json) ? [] : true
       else
         run_shellcheck(shell_files, output_type, fix: fix)
       end
diff --git a/Library/Homebrew/tap.rb b/Library/Homebrew/tap.rb
index 7a2fba9256..c41753c6e7 100644
--- a/Library/Homebrew/tap.rb
+++ b/Library/Homebrew/tap.rb
@@ -252,7 +252,7 @@ class Tap
     if official? && DEPRECATED_OFFICIAL_TAPS.include?(repo)
       odie "#{name} was deprecated. This tap is now empty and all its contents were either deleted or migrated."
     elsif user == "caskroom" || name == "phinze/cask"
-      new_repo = repo == "cask" ? "cask" : "cask-#{repo}"
+      new_repo = (repo == "cask") ? "cask" : "cask-#{repo}"
       odie "#{name} was moved. Tap homebrew/#{new_repo} instead."
     end
 
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/arch-arm-only.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/arch-arm-only.rb
index c40235d15d..d6bc73d35e 100644
--- a/Library/Homebrew/test/support/fixtures/cask/Casks/arch-arm-only.rb
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/arch-arm-only.rb
@@ -1,7 +1,8 @@
 cask "arch-arm-only" do
+  arch arm: "-arm"
+
   version "1.2.3"
   sha256 "67cdb8a02803ef37fdbf7e0be205863172e41a561ca446cd84f0d7ab35a99d94"
-  arch arm: "-arm"
 
   url "file://#{TEST_FIXTURE_DIR}/cask/caffeine#{arch}.zip"
   homepage "https://brew.sh/"
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/invalid/invalid-two-arch.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/invalid/invalid-two-arch.rb
index 15112831e6..117e59c3bc 100644
--- a/Library/Homebrew/test/support/fixtures/cask/Casks/invalid/invalid-two-arch.rb
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/invalid/invalid-two-arch.rb
@@ -1,9 +1,10 @@
 cask "invalid-two-arch" do
-  version "1.2.3"
-  sha256 "67cdb8a02803ef37fdbf7e0be205863172e41a561ca446cd84f0d7ab35a99d94"
   arch arm: "arm", intel: "intel"
   arch arm: "amd64", intel: "x86_64"
 
+  version "1.2.3"
+  sha256 "67cdb8a02803ef37fdbf7e0be205863172e41a561ca446cd84f0d7ab35a99d94"
+
   url "file://#{TEST_FIXTURE_DIR}/cask/caffeine.zip"
   homepage "https://brew.sh/"
 
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/multiple-versions.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/multiple-versions.rb
index f4e112f956..05a29fd20f 100644
--- a/Library/Homebrew/test/support/fixtures/cask/Casks/multiple-versions.rb
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/multiple-versions.rb
@@ -1,9 +1,9 @@
 cask "multiple-versions" do
+  arch arm: "arm", intel: "intel"
+  platform = on_arch_conditional arm: "darwin-arm64", intel: "darwin"
+
   version "1.2.3"
   sha256 "67cdb8a02803ef37fdbf7e0be205863172e41a561ca446cd84f0d7ab35a99d94"
-  arch arm: "arm", intel: "intel"
-
-  platform = on_arch_conditional arm: "darwin-arm64", intel: "darwin"
 
   on_big_sur do
     version "1.2.0"
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/with-depends-on-macos-failure.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/with-depends-on-macos-failure.rb
index 652ac08b8e..9dbddb789e 100644
--- a/Library/Homebrew/test/support/fixtures/cask/Casks/with-depends-on-macos-failure.rb
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/with-depends-on-macos-failure.rb
@@ -6,7 +6,7 @@ cask "with-depends-on-macos-failure" do
   homepage "https://brew.sh/with-depends-on-macos-failure"
 
   # guarantee a mismatched release
-  depends_on macos: MacOS.version == :catalina ? :mojave : :catalina
+  depends_on macos: (MacOS.version == :catalina) ? :mojave : :catalina
 
   app "Caffeine.app"
 end
diff --git a/Library/Homebrew/vendor/bundle/bundler/setup.rb b/Library/Homebrew/vendor/bundle/bundler/setup.rb
index 1f4eea3104..69885e22a4 100644
--- a/Library/Homebrew/vendor/bundle/bundler/setup.rb
+++ b/Library/Homebrew/vendor/bundle/bundler/setup.rb
@@ -86,7 +86,7 @@ $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/rspec_junit_formatter
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/rubocop-ast-1.21.0/lib"
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/ruby-progressbar-1.11.0/lib"
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/unicode-display_width-2.2.0/lib"
-$:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/rubocop-1.33.0/lib"
+$:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/rubocop-1.34.1/lib"
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/rubocop-performance-1.14.3/lib"
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/rubocop-rails-2.15.2/lib"
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/rubocop-rspec-2.12.1/lib"