diff --git a/Library/Homebrew/cask/lib/hbc/metadata.rb b/Library/Homebrew/cask/lib/hbc/metadata.rb
index 344c38ceea..030b18dd9f 100644
--- a/Library/Homebrew/cask/lib/hbc/metadata.rb
+++ b/Library/Homebrew/cask/lib/hbc/metadata.rb
@@ -22,7 +22,7 @@ module Hbc
       end
 
       path = if timestamp == :latest
-        Pathname.glob(metadata_versioned_path(version: version).join("*")).sort.last
+        Pathname.glob(metadata_versioned_path(version: version).join("*")).max
       else
         timestamp = new_timestamp if timestamp == :now
         metadata_versioned_path(version: version).join(timestamp)
diff --git a/Library/Homebrew/cli_parser.rb b/Library/Homebrew/cli_parser.rb
index 5ce769343b..dd467f3fc6 100644
--- a/Library/Homebrew/cli_parser.rb
+++ b/Library/Homebrew/cli_parser.rb
@@ -52,7 +52,7 @@ module Homebrew
       end
 
       def option_to_description(*names)
-        names.map { |name| name.to_s.sub(/\A--?/, "").tr("-", " ") }.sort.last
+        names.map { |name| name.to_s.sub(/\A--?/, "").tr("-", " ") }.max
       end
 
       def parse(cmdline_args = ARGV)
diff --git a/Library/Homebrew/constants.rb b/Library/Homebrew/constants.rb
index a98c14a387..25326075e5 100644
--- a/Library/Homebrew/constants.rb
+++ b/Library/Homebrew/constants.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
 
 # RuboCop version used for `brew style` and `brew cask style`
-HOMEBREW_RUBOCOP_VERSION = "0.54.0"
-HOMEBREW_RUBOCOP_CASK_VERSION = "~> 0.18.1" # has to be updated when RuboCop version changes
+HOMEBREW_RUBOCOP_VERSION = "0.55.0"
+HOMEBREW_RUBOCOP_CASK_VERSION = "~> 0.19.0" # has to be updated when RuboCop version changes
diff --git a/Library/Homebrew/formula.rb b/Library/Homebrew/formula.rb
index d4c248e190..452e9e9453 100644
--- a/Library/Homebrew/formula.rb
+++ b/Library/Homebrew/formula.rb
@@ -1131,7 +1131,7 @@ class Formula
     return false unless old_rack.directory?
     return false if old_rack.subdirs.empty?
 
-    tap == Tab.for_keg(old_rack.subdirs.sort.first).tap
+    tap == Tab.for_keg(old_rack.subdirs.min).tap
   end
 
   # @private
diff --git a/Library/Homebrew/keg.rb b/Library/Homebrew/keg.rb
index 7e930cc375..02e318624b 100644
--- a/Library/Homebrew/keg.rb
+++ b/Library/Homebrew/keg.rb
@@ -129,7 +129,7 @@ class Keg
         f_kegs = kegs_by_source[[f.name, f.tap]]
         next unless f_kegs
 
-        f_kegs.sort_by(&:version).last
+        f_kegs.max_by(&:version)
       end.compact
 
       next if required_kegs.empty?