diff --git a/Library/Homebrew/rubocops/cask/ast/cask_block.rb b/Library/Homebrew/rubocops/cask/ast/cask_block.rb
index 4f45f6771c..ac0dca7592 100644
--- a/Library/Homebrew/rubocops/cask/ast/cask_block.rb
+++ b/Library/Homebrew/rubocops/cask/ast/cask_block.rb
@@ -36,7 +36,15 @@ module RuboCop
         end
 
         def toplevel_stanzas
-          @toplevel_stanzas ||= stanzas.select(&:toplevel_stanza?)
+          # If a `cask` block only contains one stanza, it is that stanza's direct parent,
+          # otherwise stanzas are grouped in a block and `cask` is that block's parent.
+          is_toplevel_stanza = if cask_body.begin_block?
+            ->(stanza) { stanza.parent_node.parent.cask_block? }
+          else
+            ->(stanza) { stanza.parent_node.cask_block? }
+          end
+
+          @toplevel_stanzas ||= stanzas.select(&is_toplevel_stanza)
         end
 
         def sorted_toplevel_stanzas
diff --git a/Library/Homebrew/rubocops/cask/ast/stanza.rb b/Library/Homebrew/rubocops/cask/ast/stanza.rb
index 2088a43655..88badac8cd 100644
--- a/Library/Homebrew/rubocops/cask/ast/stanza.rb
+++ b/Library/Homebrew/rubocops/cask/ast/stanza.rb
@@ -52,10 +52,6 @@ module RuboCop
           stanza_group == other.stanza_group
         end
 
-        def toplevel_stanza?
-          parent_node.cask_block? || parent_node.parent.cask_block?
-        end
-
         def ==(other)
           self.class == other.class && stanza_node == other.stanza_node
         end
diff --git a/Library/Homebrew/rubocops/cask/extend/node.rb b/Library/Homebrew/rubocops/cask/extend/node.rb
index 20e1e4b7cc..ec79aa4f3f 100644
--- a/Library/Homebrew/rubocops/cask/extend/node.rb
+++ b/Library/Homebrew/rubocops/cask/extend/node.rb
@@ -17,6 +17,8 @@ module RuboCop
       def_node_matcher :cask_block?, "(block (send nil? :cask _) args ...)"
       def_node_matcher :arch_variable?, "(lvasgn _ (send nil? :on_arch_conditional ...))"
 
+      def_node_matcher :begin_block?, "(begin ...)"
+
       def stanza?
         return true if arch_variable?