diff --git a/Library/Homebrew/rubocops/cask/constants/stanza.rb b/Library/Homebrew/rubocops/cask/constants/stanza.rb
index 00c909b63d..0fff837f3f 100644
--- a/Library/Homebrew/rubocops/cask/constants/stanza.rb
+++ b/Library/Homebrew/rubocops/cask/constants/stanza.rb
@@ -6,10 +6,15 @@ module RuboCop
     # Constants available globally for use in all cask cops.
     module Constants
       ON_SYSTEM_METHODS = [:arm, :intel, *MacOSVersions::SYMBOLS.keys].map { |option| :"on_#{option}" }.freeze
+      ON_SYSTEM_METHODS_STANZA_ORDER = [
+        :arm,
+        :intel,
+        *MacOSVersions::SYMBOLS.reverse_each.to_h.keys, # Oldest OS blocks first since that's more common in Casks.
+      ].map { |option, _| :"on_#{option}" }.freeze
 
       STANZA_GROUPS = [
         [:arch, :on_arch_conditional],
-        ON_SYSTEM_METHODS,
+        ON_SYSTEM_METHODS_STANZA_ORDER,
         [:version, :sha256],
         [:language],
         [:url, :appcast, :name, :desc, :homepage],
diff --git a/Library/Homebrew/test/rubocops/cask/stanza_order_spec.rb b/Library/Homebrew/test/rubocops/cask/stanza_order_spec.rb
index b33db17f4d..b53f937e6e 100644
--- a/Library/Homebrew/test/rubocops/cask/stanza_order_spec.rb
+++ b/Library/Homebrew/test/rubocops/cask/stanza_order_spec.rb
@@ -604,11 +604,11 @@ describe RuboCop::Cop::Cask::StanzaOrder do
 
     let(:expected_offenses) do
       [{
-        message:  "`on_catalina` stanza out of order",
+        message:  "`on_ventura` stanza out of order",
         severity: :convention,
-        line:     6,
+        line:     2,
         column:   2,
-        source:   "on_catalina do\n    url \"https://foo.brew.sh/foo-catalina.zip\"\n    sha256 :no_check\n  end",
+        source:   "on_ventura do\n    url \"https://foo.brew.sh/foo-ventura.zip\"\n    sha256 :no_check\n  end",
       }, {
         message:  "`on_mojave` stanza out of order",
         severity: :convention,
@@ -627,20 +627,20 @@ describe RuboCop::Cop::Cask::StanzaOrder do
     let(:correct_source) do
       <<~CASK
         cask "foo" do
-          on_ventura do
-            url "https://foo.brew.sh/foo-ventura.zip"
-            sha256 :no_check
-          end
-          on_big_sur do
-            url "https://foo.brew.sh/foo-big-sur.zip"
+          on_mojave do
+            url "https://foo.brew.sh/foo-mojave.zip"
             sha256 :no_check
           end
           on_catalina do
             url "https://foo.brew.sh/foo-catalina.zip"
             sha256 :no_check
           end
-          on_mojave do
-            url "https://foo.brew.sh/foo-mojave.zip"
+          on_big_sur do
+            url "https://foo.brew.sh/foo-big-sur.zip"
+            sha256 :no_check
+          end
+          on_ventura do
+            url "https://foo.brew.sh/foo-ventura.zip"
             sha256 :no_check
           end