diff --git a/Library/Homebrew/cli/args.rb b/Library/Homebrew/cli/args.rb
index 0e5ecd7263b2b..70eda0ea05dca 100644
--- a/Library/Homebrew/cli/args.rb
+++ b/Library/Homebrew/cli/args.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 require "ostruct"
diff --git a/Library/Homebrew/extend/os/linux/cleanup.rb b/Library/Homebrew/extend/os/linux/cleanup.rb
index 85a53d78b7cc4..85f0c3e66782e 100644
--- a/Library/Homebrew/extend/os/linux/cleanup.rb
+++ b/Library/Homebrew/extend/os/linux/cleanup.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 module Homebrew
diff --git a/Library/Homebrew/extend/os/linux/dependency_collector.rb b/Library/Homebrew/extend/os/linux/dependency_collector.rb
index 2e0952b4bcac6..135edc6593f5d 100644
--- a/Library/Homebrew/extend/os/linux/dependency_collector.rb
+++ b/Library/Homebrew/extend/os/linux/dependency_collector.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 require "os/linux/glibc"
diff --git a/Library/Homebrew/extend/os/linux/diagnostic.rb b/Library/Homebrew/extend/os/linux/diagnostic.rb
index 234808224e24f..468a6b6587b49 100644
--- a/Library/Homebrew/extend/os/linux/diagnostic.rb
+++ b/Library/Homebrew/extend/os/linux/diagnostic.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 require "tempfile"
diff --git a/Library/Homebrew/extend/os/linux/formula.rb b/Library/Homebrew/extend/os/linux/formula.rb
index 85a3700119a7a..1efa971637b6e 100644
--- a/Library/Homebrew/extend/os/linux/formula.rb
+++ b/Library/Homebrew/extend/os/linux/formula.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 class Formula
diff --git a/Library/Homebrew/extend/os/linux/formula_installer.rb b/Library/Homebrew/extend/os/linux/formula_installer.rb
index 7a118ae87e191..d1286b8a7458f 100644
--- a/Library/Homebrew/extend/os/linux/formula_installer.rb
+++ b/Library/Homebrew/extend/os/linux/formula_installer.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 class FormulaInstaller
diff --git a/Library/Homebrew/extend/os/linux/keg.rb b/Library/Homebrew/extend/os/linux/keg.rb
index 9b0eaf81ddcf1..0f30b67899a91 100644
--- a/Library/Homebrew/extend/os/linux/keg.rb
+++ b/Library/Homebrew/extend/os/linux/keg.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 class Keg
diff --git a/Library/Homebrew/extend/os/linux/parser.rb b/Library/Homebrew/extend/os/linux/parser.rb
index 9d76e9c9b3d78..849a84d73e8b8 100644
--- a/Library/Homebrew/extend/os/linux/parser.rb
+++ b/Library/Homebrew/extend/os/linux/parser.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 module Homebrew
diff --git a/Library/Homebrew/extend/os/linux/simulate_system.rb b/Library/Homebrew/extend/os/linux/simulate_system.rb
index 35ddeb8740e61..007f2c4e8372d 100644
--- a/Library/Homebrew/extend/os/linux/simulate_system.rb
+++ b/Library/Homebrew/extend/os/linux/simulate_system.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 module Homebrew
diff --git a/Library/Homebrew/extend/os/mac/cleaner.rb b/Library/Homebrew/extend/os/mac/cleaner.rb
index 600eec82e2cae..5ca8a8243aab0 100644
--- a/Library/Homebrew/extend/os/mac/cleaner.rb
+++ b/Library/Homebrew/extend/os/mac/cleaner.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 class Cleaner
diff --git a/Library/Homebrew/extend/os/mac/cleanup.rb b/Library/Homebrew/extend/os/mac/cleanup.rb
index c61275aeb70be..32e536319029a 100644
--- a/Library/Homebrew/extend/os/mac/cleanup.rb
+++ b/Library/Homebrew/extend/os/mac/cleanup.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 module Homebrew
diff --git a/Library/Homebrew/extend/os/mac/dependency_collector.rb b/Library/Homebrew/extend/os/mac/dependency_collector.rb
index 6f97069e703fe..42024fc41f385 100644
--- a/Library/Homebrew/extend/os/mac/dependency_collector.rb
+++ b/Library/Homebrew/extend/os/mac/dependency_collector.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 class DependencyCollector
diff --git a/Library/Homebrew/extend/os/mac/dev-cmd/bottle.rb b/Library/Homebrew/extend/os/mac/dev-cmd/bottle.rb
index f6313608ca9dd..9743384f466ad 100644
--- a/Library/Homebrew/extend/os/mac/dev-cmd/bottle.rb
+++ b/Library/Homebrew/extend/os/mac/dev-cmd/bottle.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 module Homebrew
diff --git a/Library/Homebrew/extend/os/mac/development_tools.rb b/Library/Homebrew/extend/os/mac/development_tools.rb
index d53f77a858a58..524f084f53f44 100644
--- a/Library/Homebrew/extend/os/mac/development_tools.rb
+++ b/Library/Homebrew/extend/os/mac/development_tools.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 require "os/mac/xcode"
diff --git a/Library/Homebrew/extend/os/mac/diagnostic.rb b/Library/Homebrew/extend/os/mac/diagnostic.rb
index 923fd1dae5dae..d15864840ecba 100644
--- a/Library/Homebrew/extend/os/mac/diagnostic.rb
+++ b/Library/Homebrew/extend/os/mac/diagnostic.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 module Homebrew
diff --git a/Library/Homebrew/extend/os/mac/extend/ENV/std.rb b/Library/Homebrew/extend/os/mac/extend/ENV/std.rb
index 37a3a335fd897..78840f57dc5c0 100644
--- a/Library/Homebrew/extend/os/mac/extend/ENV/std.rb
+++ b/Library/Homebrew/extend/os/mac/extend/ENV/std.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 module Stdenv
diff --git a/Library/Homebrew/extend/os/mac/extend/ENV/super.rb b/Library/Homebrew/extend/os/mac/extend/ENV/super.rb
index c18a8e95c23d6..391a7066981e1 100644
--- a/Library/Homebrew/extend/os/mac/extend/ENV/super.rb
+++ b/Library/Homebrew/extend/os/mac/extend/ENV/super.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 module Superenv
diff --git a/Library/Homebrew/extend/os/mac/formula.rb b/Library/Homebrew/extend/os/mac/formula.rb
index 1d427eed33434..f474deef38840 100644
--- a/Library/Homebrew/extend/os/mac/formula.rb
+++ b/Library/Homebrew/extend/os/mac/formula.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 class Formula
diff --git a/Library/Homebrew/extend/os/mac/formula_installer.rb b/Library/Homebrew/extend/os/mac/formula_installer.rb
index 8da9417fcfc11..8b96c112a9c4a 100644
--- a/Library/Homebrew/extend/os/mac/formula_installer.rb
+++ b/Library/Homebrew/extend/os/mac/formula_installer.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 class FormulaInstaller
diff --git a/Library/Homebrew/extend/os/mac/hardware/cpu.rb b/Library/Homebrew/extend/os/mac/hardware/cpu.rb
index 0bcd281b2c0ec..20caa82f8a728 100644
--- a/Library/Homebrew/extend/os/mac/hardware/cpu.rb
+++ b/Library/Homebrew/extend/os/mac/hardware/cpu.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 require "macho"
diff --git a/Library/Homebrew/extend/os/mac/keg.rb b/Library/Homebrew/extend/os/mac/keg.rb
index 76a1d9292d140..9c3a79de42f17 100644
--- a/Library/Homebrew/extend/os/mac/keg.rb
+++ b/Library/Homebrew/extend/os/mac/keg.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 require "system_command"
diff --git a/Library/Homebrew/extend/os/mac/keg_relocate.rb b/Library/Homebrew/extend/os/mac/keg_relocate.rb
index dee1be9545777..bd9180593219d 100644
--- a/Library/Homebrew/extend/os/mac/keg_relocate.rb
+++ b/Library/Homebrew/extend/os/mac/keg_relocate.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 class Keg
diff --git a/Library/Homebrew/extend/os/mac/linkage_checker.rb b/Library/Homebrew/extend/os/mac/linkage_checker.rb
index 9baba42a7d250..fedb73be7a395 100644
--- a/Library/Homebrew/extend/os/mac/linkage_checker.rb
+++ b/Library/Homebrew/extend/os/mac/linkage_checker.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 class LinkageChecker
diff --git a/Library/Homebrew/extend/os/mac/readall.rb b/Library/Homebrew/extend/os/mac/readall.rb
index 31ef4ebb92554..fcd34fc8927dd 100644
--- a/Library/Homebrew/extend/os/mac/readall.rb
+++ b/Library/Homebrew/extend/os/mac/readall.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 module Readall
diff --git a/Library/Homebrew/extend/os/mac/simulate_system.rb b/Library/Homebrew/extend/os/mac/simulate_system.rb
index 62f0d2d3bb8c9..7272b56bc4f02 100644
--- a/Library/Homebrew/extend/os/mac/simulate_system.rb
+++ b/Library/Homebrew/extend/os/mac/simulate_system.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 module Homebrew
diff --git a/Library/Homebrew/extend/os/mac/system_config.rb b/Library/Homebrew/extend/os/mac/system_config.rb
index b15bdc5268817..a41fa5331eb55 100644
--- a/Library/Homebrew/extend/os/mac/system_config.rb
+++ b/Library/Homebrew/extend/os/mac/system_config.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 require "system_command"
diff --git a/Library/Homebrew/ignorable.rb b/Library/Homebrew/ignorable.rb
index 2b5c318f1ea28..15d1c8213acd7 100644
--- a/Library/Homebrew/ignorable.rb
+++ b/Library/Homebrew/ignorable.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: true # This cannot be `# typed: strict` due to the use of `undef`.
 # frozen_string_literal: true
 
 require "warnings"