diff --git a/Library/Homebrew/rubocops/cask/ast/cask_block.rb b/Library/Homebrew/rubocops/cask/ast/cask_block.rb
index 06825c26bb..9d19220365 100644
--- a/Library/Homebrew/rubocops/cask/ast/cask_block.rb
+++ b/Library/Homebrew/rubocops/cask/ast/cask_block.rb
@@ -6,27 +6,58 @@ require "forwardable"
 module RuboCop
   module Cask
     module AST
-      # This class wraps the AST block node that represents the entire cask
-      # definition. It includes various helper methods to aid cops in their
-      # analysis.
-      class CaskBlock
-        extend Forwardable
+      class StanzaBlock
+        extend T::Helpers
+        extend T::Sig
 
+        sig { returns(RuboCop::AST::BlockNode) }
+        attr_reader :block_node
+
+        sig { returns(T::Array[Parser::Source::Comment]) }
+        attr_reader :comments
+
+        sig { params(block_node: RuboCop::AST::BlockNode, comments: T::Array[Parser::Source::Comment]).void }
         def initialize(block_node, comments)
           @block_node = block_node
           @comments = comments
         end
 
-        attr_reader :block_node, :comments
+        sig { returns(T::Array[Stanza]) }
+        def stanzas
+          return [] unless (block_body = block_node.block_body)
 
-        alias cask_node block_node
+          # If a block only contains one stanza, it is that stanza's direct parent, otherwise
+          # stanzas are grouped in a nested block and the block is that nested block's parent.
+          is_stanza = if block_body.begin_block?
+            ->(node) { node.parent.parent == block_node }
+          else
+            ->(node) { node.parent == block_node }
+          end
+
+          @stanzas ||= block_body.each_node
+                                 .select(&:stanza?)
+                                 .select(&is_stanza)
+                                 .map { |node| Stanza.new(node, comments) }
+        end
+      end
+
+      # This class wraps the AST block node that represents the entire cask
+      # definition. It includes various helper methods to aid cops in their
+      # analysis.
+      class CaskBlock < StanzaBlock
+        extend Forwardable
+
+        def cask_node
+          block_node
+        end
 
         def_delegator :cask_node, :block_body, :cask_body
 
         def header
-          @header ||= CaskHeader.new(cask_node.method_node)
+          @header ||= CaskHeader.new(block_node.method_node)
         end
 
+        # TODO: Use `StanzaBlock#stanzas` for all cops, where possible.
         def stanzas
           return [] unless cask_body
 
@@ -46,29 +77,6 @@ module RuboCop
 
           @toplevel_stanzas ||= stanzas.select(&is_toplevel_stanza)
         end
-
-        def sorted_toplevel_stanzas
-          @sorted_toplevel_stanzas ||= sort_stanzas(toplevel_stanzas)
-        end
-
-        private
-
-        def sort_stanzas(stanzas)
-          stanzas.sort do |s1, s2|
-            i1 = stanza_order_index(s1)
-            i2 = stanza_order_index(s2)
-            if i1 == i2 || i1.blank? || i2.blank?
-              i1 = stanzas.index(s1)
-              i2 = stanzas.index(s2)
-            end
-            i1 - i2
-          end
-        end
-
-        def stanza_order_index(stanza)
-          stanza_name = stanza.respond_to?(:method_name) ? stanza.method_name : stanza.stanza_name
-          Constants::STANZA_ORDER.index(stanza_name)
-        end
       end
     end
   end
diff --git a/Library/Homebrew/rubocops/cask/ast/stanza.rb b/Library/Homebrew/rubocops/cask/ast/stanza.rb
index 68b6de8218..e9cc111b3a 100644
--- a/Library/Homebrew/rubocops/cask/ast/stanza.rb
+++ b/Library/Homebrew/rubocops/cask/ast/stanza.rb
@@ -23,6 +23,7 @@ module RuboCop
 
         def_delegator :stanza_node, :parent, :parent_node
         def_delegator :stanza_node, :arch_variable?
+        def_delegator :stanza_node, :on_system_block?
 
         def source_range
           stanza_node.location_expression
@@ -48,6 +49,10 @@ module RuboCop
           Constants::STANZA_GROUP_HASH[stanza_name]
         end
 
+        def stanza_index
+          Constants::STANZA_ORDER.index(stanza_name)
+        end
+
         def same_group?(other)
           stanza_group == other.stanza_group
         end
@@ -65,7 +70,6 @@ module RuboCop
         def ==(other)
           self.class == other.class && stanza_node == other.stanza_node
         end
-
         alias eql? ==
 
         Constants::STANZA_ORDER.each do |stanza_name|
diff --git a/Library/Homebrew/rubocops/cask/extend/node.rb b/Library/Homebrew/rubocops/cask/extend/node.rb
index 2fa13eabc7..5dbd6b9770 100644
--- a/Library/Homebrew/rubocops/cask/extend/node.rb
+++ b/Library/Homebrew/rubocops/cask/extend/node.rb
@@ -5,6 +5,8 @@ module RuboCop
   module AST
     # Extensions for RuboCop's AST Node class.
     class Node
+      extend T::Sig
+
       include RuboCop::Cask::Constants
 
       def_node_matcher :method_node, "{$(send ...) (block $(send ...) ...)}"
@@ -15,11 +17,17 @@ module RuboCop
       def_node_matcher :val_node,    "{(pair _ $_) (hash (pair _ $_) ...)}"
 
       def_node_matcher :cask_block?, "(block (send nil? :cask ...) args ...)"
-      def_node_matcher :on_system_block?, "(block (send nil? {#{ON_SYSTEM_METHODS.map(&:inspect).join(" ")}} ...) args ...)"
+      def_node_matcher :on_system_block?,
+                       "(block (send nil? {#{ON_SYSTEM_METHODS.map(&:inspect).join(" ")}} ...) args ...)"
       def_node_matcher :arch_variable?, "(lvasgn _ (send nil? :on_arch_conditional ...))"
 
       def_node_matcher :begin_block?, "(begin ...)"
 
+      sig { returns(T::Boolean) }
+      def cask_on_system_block?
+        (on_system_block? && each_ancestor.any?(&:cask_block?)) || false
+      end
+
       def stanza?
         return true if arch_variable?
 
diff --git a/Library/Homebrew/rubocops/cask/mixin/cask_help.rb b/Library/Homebrew/rubocops/cask/mixin/cask_help.rb
index 8126c33660..093b93ec61 100644
--- a/Library/Homebrew/rubocops/cask/mixin/cask_help.rb
+++ b/Library/Homebrew/rubocops/cask/mixin/cask_help.rb
@@ -6,31 +6,39 @@ module RuboCop
     module Cask
       # Common functionality for cops checking casks.
       module CaskHelp
-        extend T::Helpers
+        prepend CommentsHelp
 
-        abstract!
-
-        sig { abstract.params(cask_block: RuboCop::Cask::AST::CaskBlock).void }
+        sig { overridable.params(cask_block: RuboCop::Cask::AST::CaskBlock).void }
         def on_cask(cask_block); end
 
+        sig { overridable.params(cask_stanza_block: RuboCop::Cask::AST::StanzaBlock).void }
         def on_cask_stanza_block(cask_stanza_block); end
 
+        # FIXME: Workaround until https://github.com/rubocop/rubocop/pull/11858 is released.
+        def find_end_line(node)
+          return node.loc.end.line if node.block_type? || node.numblock_type?
+
+          super
+        end
+
+        sig { params(block_node: RuboCop::AST::BlockNode).void }
         def on_block(block_node)
           super if defined? super
 
-          if respond_to?(:on_cask_stanza_block) && (block_node.cask_block? || block_node.on_system_block?)
-            on_cask_stanza_block(block_node)
-          end
+          return if !block_node.cask_block? && !block_node.cask_on_system_block?
 
-          if respond_to?(:on_cask) && block_node.cask_block?
-            comments = processed_source.comments
-            cask_block = RuboCop::Cask::AST::CaskBlock.new(block_node, comments)
-            on_cask(cask_block)
-          end
+          comments = comments_in_range(block_node).to_a
+          stanza_block = RuboCop::Cask::AST::StanzaBlock.new(block_node, comments)
+          on_cask_stanza_block(stanza_block)
+
+          return unless block_node.cask_block?
+
+          cask_block = RuboCop::Cask::AST::CaskBlock.new(block_node, comments)
+          on_cask(cask_block)
         end
 
         def on_system_methods(cask_stanzas)
-          cask_stanzas.select { |s| RuboCop::Cask::Constants::ON_SYSTEM_METHODS.include?(s.stanza_name) }
+          cask_stanzas.select(&:on_system_block?)
         end
 
         def inner_stanzas(block_node, comments)
diff --git a/Library/Homebrew/rubocops/cask/stanza_order.rb b/Library/Homebrew/rubocops/cask/stanza_order.rb
index 3bb27d366b..8ec1929138 100644
--- a/Library/Homebrew/rubocops/cask/stanza_order.rb
+++ b/Library/Homebrew/rubocops/cask/stanza_order.rb
@@ -9,45 +9,57 @@ module RuboCop
       # This cop checks that a cask's stanzas are ordered correctly, including nested within `on_*` blocks.
       # @see https://docs.brew.sh/Cask-Cookbook#stanza-order
       class StanzaOrder < Base
+        include IgnoredNode
         extend Forwardable
         extend AutoCorrector
         include CaskHelp
 
         MESSAGE = "`%<stanza>s` stanza out of order"
 
-        def on_cask(cask_block)
-          @cask_block = cask_block
+        def on_cask_stanza_block(stanza_block)
+          stanzas = stanza_block.stanzas
+          ordered_stanzas = sort_stanzas(stanzas)
 
-          # Find all the stanzas that are direct children of the cask block or one of its `on_*` blocks.
-          puts "toplevel_stanzas: #{toplevel_stanzas.map(&:stanza_name).inspect}"
-          outer_and_inner_stanzas = toplevel_stanzas + toplevel_stanzas.map do |stanza|
-            return stanza unless stanza.method_node&.block_type?
+          return if stanzas == ordered_stanzas
 
-            inner_stanzas(stanza.method_node, stanza.comments)
-          end
+          stanzas.zip(ordered_stanzas).each do |stanza_before, stanza_after|
+            next if stanza_before == stanza_after
 
-          puts "outer_and_inner_stanzas: #{outer_and_inner_stanzas.flatten.map(&:stanza_name).inspect}"
-          add_offenses(outer_and_inner_stanzas.flatten)
-        end
+            add_offense(
+              stanza_before.method_node,
+              message: format(MESSAGE, stanza: stanza_before.stanza_name),
+            ) do |corrector|
+              next if part_of_ignored_node?(stanza_before.method_node)
 
-        private
+              corrector.replace(
+                stanza_before.source_range_with_comments,
+                stanza_after.source_with_comments,
+              )
 
-        attr_reader :cask_block
-
-        def_delegators :cask_block, :cask_node, :toplevel_stanzas
-
-        def add_offenses(outer_and_inner_stanzas)
-          outer_and_inner_stanzas.each_cons(2) do |stanza1, stanza2|
-            next if stanza_order_index(stanza1.stanza_name) < stanza_order_index(stanza2.stanza_name)
-
-            puts "#{stanza2.stanza_name} should come before #{stanza1.stanza_name}"
-            add_offense(stanza1.method_node, message: format(MESSAGE, stanza: stanza1.stanza_name)) do |corrector|
-              # TODO: Move the stanza to the correct location.
+              # Ignore node so that nested content is not auto-corrected and clobbered.
+              ignore_node(stanza_before.method_node)
             end
           end
         end
 
-        def stanza_order_index(stanza_name)
+        private
+
+        def sort_stanzas(stanzas)
+          stanzas.sort do |stanza1, stanza2|
+            i1 = stanza1.stanza_index
+            i2 = stanza2.stanza_index
+
+            if i1 == i2
+              i1 = stanzas.index(stanza1)
+              i2 = stanzas.index(stanza2)
+            end
+
+            i1 - i2
+          end
+        end
+
+        def stanza_order_index(stanza)
+          stanza_name = stanza.respond_to?(:method_name) ? stanza.method_name : stanza.stanza_name
           RuboCop::Cask::Constants::STANZA_ORDER.index(stanza_name)
         end
       end
diff --git a/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi b/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi
index 5eed0ed4c0..95271192b2 100644
--- a/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi
+++ b/Library/Homebrew/sorbet/rbi/hidden-definitions/hidden.rbi
@@ -6373,6 +6373,8 @@ class RuboCop::AST::Node
 
   def method_node(param0=T.unsafe(nil)); end
 
+  def on_system_block?(param0=T.unsafe(nil)); end
+
   def val_node(param0=T.unsafe(nil)); end
 end
 
@@ -6504,12 +6506,61 @@ class RuboCop::Cask::AST::Stanza
   def zap?(); end
 end
 
+module RuboCop::Cop::Cask::CaskHelp
+  include ::RuboCop::Cop::CommentsHelp
+end
+
 module RuboCop::Cop::Cask::CaskHelp
   extend ::T::Private::Abstract::Hooks
   extend ::T::InterfaceWrapper::Helpers
 end
 
+class RuboCop::Cop::Cask::Desc
+  include ::RuboCop::Cop::CommentsHelp
+end
+
+class RuboCop::Cop::Cask::HomepageUrlTrailingSlash
+  include ::RuboCop::Cop::CommentsHelp
+end
+
+class RuboCop::Cop::Cask::NoDslVersion
+  include ::RuboCop::Cop::CommentsHelp
+end
+
+class RuboCop::Cop::Cask::NoOverrides
+  include ::RuboCop::Cop::CommentsHelp
+end
+
+module RuboCop::Cop::Cask::OnDescStanza
+  include ::RuboCop::Cop::CommentsHelp
+end
+
+module RuboCop::Cop::Cask::OnHomepageStanza
+  include ::RuboCop::Cop::CommentsHelp
+end
+
+class RuboCop::Cop::Cask::OnSystemConditionals
+  include ::RuboCop::Cop::CommentsHelp
+end
+
+module RuboCop::Cop::Cask::OnUrlStanza
+  include ::RuboCop::Cop::CommentsHelp
+end
+
+class RuboCop::Cop::Cask::StanzaGrouping
+  include ::RuboCop::Cop::CommentsHelp
+end
+
+class RuboCop::Cop::Cask::StanzaOrder
+  include ::RuboCop::Cop::CommentsHelp
+end
+
+class RuboCop::Cop::Cask::Url
+  include ::RuboCop::Cop::CommentsHelp
+end
+
 class RuboCop::Cop::Cask::Variables
+  include ::RuboCop::Cop::CommentsHelp
   def variable_assignment(param0); end
 end
 
diff --git a/Library/Homebrew/test/rubocops/cask/shared_examples/cask_cop.rb b/Library/Homebrew/test/rubocops/cask/shared_examples/cask_cop.rb
index 6436b09c95..cc0235647c 100644
--- a/Library/Homebrew/test/rubocops/cask/shared_examples/cask_cop.rb
+++ b/Library/Homebrew/test/rubocops/cask/shared_examples/cask_cop.rb
@@ -39,8 +39,24 @@ module CaskCop
     expect(actual.location.source).to eq(expected[:source])
   end
 
+  # TODO: Replace with `expect_correction` from `rubocop-rspec`.
   def expect_autocorrected_source(source, correct_source)
-    new_source = autocorrect_source(source)
-    expect(new_source).to eq(Array(correct_source).join("\n"))
+    correct_source = Array(correct_source).join("\n")
+
+    current_source = source
+
+    # RuboCop runs auto-correction in a loop to handle nested offenses.
+    loop do
+      current_source = autocorrect_source(current_source)
+
+      if (ignored_nodes = cop.instance_variable_get(:@ignored_nodes)) && ignored_nodes.any?
+        ignored_nodes.clear
+        next
+      end
+
+      break
+    end
+
+    expect(current_source).to eq correct_source
   end
 end
diff --git a/Library/Homebrew/test/rubocops/cask/stanza_order_spec.rb b/Library/Homebrew/test/rubocops/cask/stanza_order_spec.rb
index bbf7582ee1..cfa658257c 100644
--- a/Library/Homebrew/test/rubocops/cask/stanza_order_spec.rb
+++ b/Library/Homebrew/test/rubocops/cask/stanza_order_spec.rb
@@ -489,8 +489,8 @@ describe RuboCop::Cop::Cask::StanzaOrder do
           end
           on_intel do
             version :latest
-            sha256 :no_check
 
+            sha256 :no_check
             url "https://foo.brew.sh/foo-intel.zip"
           end
         end
@@ -533,24 +533,24 @@ describe RuboCop::Cop::Cask::StanzaOrder do
       <<~CASK
         cask "foo" do
           on_mojave do
-            version "0.6"
+            version :latest
             sha256 "ghi789"
             url "https://foo.brew.sh/foo-mojave.zip"
           end
           on_catalina do
-            sha256 "def456"
             version "0.7"
+            sha256 "def456"
             url "https://foo.brew.sh/foo-catalina.zip"
           end
           on_big_sur do
-            version "0.8"
+            version :latest
             sha256 "jkl012"
 
             url "https://foo.brew.sh/foo-big-sur.zip"
           end
           on_ventura do
             version :latest
-            sha256 :no_check
+            sha256 "abc123"
             url "https://foo.brew.sh/foo-ventura.zip"
           end
         end