diff --git a/Library/Homebrew/cask/dsl/caveats.rb b/Library/Homebrew/cask/dsl/caveats.rb
index bc047275d0..f34a55cea5 100644
--- a/Library/Homebrew/cask/dsl/caveats.rb
+++ b/Library/Homebrew/cask/dsl/caveats.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 module Cask
diff --git a/Library/Homebrew/cask/info.rb b/Library/Homebrew/cask/info.rb
index 6c540f40a8..0420a20a0b 100644
--- a/Library/Homebrew/cask/info.rb
+++ b/Library/Homebrew/cask/info.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "json"
diff --git a/Library/Homebrew/cask/list.rb b/Library/Homebrew/cask/list.rb
index e0723e5f88..287730d085 100644
--- a/Library/Homebrew/cask/list.rb
+++ b/Library/Homebrew/cask/list.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cask/artifact/relocated"
diff --git a/Library/Homebrew/cmd/cleanup.rb b/Library/Homebrew/cmd/cleanup.rb
index 45002766ee..897cd07df5 100644
--- a/Library/Homebrew/cmd/cleanup.rb
+++ b/Library/Homebrew/cmd/cleanup.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cleanup"
diff --git a/Library/Homebrew/dependency.rb b/Library/Homebrew/dependency.rb
index d556924d74..15ea12ecbd 100644
--- a/Library/Homebrew/dependency.rb
+++ b/Library/Homebrew/dependency.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "dependable"
diff --git a/Library/Homebrew/extend/os/cleanup.rb b/Library/Homebrew/extend/os/cleanup.rb
index f96bca2d0f..983b23a2ea 100644
--- a/Library/Homebrew/extend/os/cleanup.rb
+++ b/Library/Homebrew/extend/os/cleanup.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 if OS.mac?
diff --git a/Library/Homebrew/extend/os/linux/cleanup.rb b/Library/Homebrew/extend/os/linux/cleanup.rb
index 82aab766f9..d486f6a112 100644
--- a/Library/Homebrew/extend/os/linux/cleanup.rb
+++ b/Library/Homebrew/extend/os/linux/cleanup.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 module Homebrew
diff --git a/Library/Homebrew/extend/os/linux/cmd/update-report.rb b/Library/Homebrew/extend/os/linux/cmd/update-report.rb
index 7471633287..a78bf2fa7f 100644
--- a/Library/Homebrew/extend/os/linux/cmd/update-report.rb
+++ b/Library/Homebrew/extend/os/linux/cmd/update-report.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 module Homebrew
diff --git a/Library/Homebrew/extend/os/linux/keg.rb b/Library/Homebrew/extend/os/linux/keg.rb
index 72b6f360cd..9b0eaf81dd 100644
--- a/Library/Homebrew/extend/os/linux/keg.rb
+++ b/Library/Homebrew/extend/os/linux/keg.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 class Keg
diff --git a/Library/Homebrew/extend/os/mac/cleanup.rb b/Library/Homebrew/extend/os/mac/cleanup.rb
index 549e09eaca..8fa20b62af 100644
--- a/Library/Homebrew/extend/os/mac/cleanup.rb
+++ b/Library/Homebrew/extend/os/mac/cleanup.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 module Homebrew
diff --git a/Library/Homebrew/startup/bootsnap.rb b/Library/Homebrew/startup/bootsnap.rb
index a6d53b6571..81027de947 100644
--- a/Library/Homebrew/startup/bootsnap.rb
+++ b/Library/Homebrew/startup/bootsnap.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 # Disable Rails cops, as we haven't required active_support yet.
diff --git a/Library/Homebrew/test/support/helper/integration_mocks.rb b/Library/Homebrew/test/support/helper/integration_mocks.rb
index 245a2aef0e..13e19d0116 100644
--- a/Library/Homebrew/test/support/helper/integration_mocks.rb
+++ b/Library/Homebrew/test/support/helper/integration_mocks.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 module Homebrew
diff --git a/Library/Homebrew/test/utils/repology_spec.rb b/Library/Homebrew/test/utils/repology_spec.rb
index 5172420a8d..0903f3a76a 100644
--- a/Library/Homebrew/test/utils/repology_spec.rb
+++ b/Library/Homebrew/test/utils/repology_spec.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "utils/repology"
diff --git a/Library/Homebrew/utils/popen.rb b/Library/Homebrew/utils/popen.rb
index 36c2b65851..733923257d 100644
--- a/Library/Homebrew/utils/popen.rb
+++ b/Library/Homebrew/utils/popen.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 module Utils