diff --git a/Library/Homebrew/dev-cmd/typecheck.rb b/Library/Homebrew/dev-cmd/typecheck.rb
index 05aa183035..1bd80123a9 100644
--- a/Library/Homebrew/dev-cmd/typecheck.rb
+++ b/Library/Homebrew/dev-cmd/typecheck.rb
@@ -64,6 +64,9 @@ module Homebrew
         tapioca_args = ["--exclude", *excluded_gems, "--typed-overrides", *typed_overrides]
         tapioca_args << "--all" if args.update_all?
 
+        ohai "Updating homegrown RBI files..."
+        safe_system "bundle", "exec", "ruby", "sorbet/custom_generators/tty.rb"
+
         ohai "Updating Tapioca RBI files..."
         safe_system "bundle", "exec", "tapioca", "gem", *tapioca_args
         safe_system "bundle", "exec", "parlour"
diff --git a/Library/Homebrew/sorbet/custom_generators/tty.rb b/Library/Homebrew/sorbet/custom_generators/tty.rb
index 1704bea2b8..ff5e22b985 100644
--- a/Library/Homebrew/sorbet/custom_generators/tty.rb
+++ b/Library/Homebrew/sorbet/custom_generators/tty.rb
@@ -1,12 +1,13 @@
 # typed: true
 # frozen_string_literal: true
 
+require_relative "../../global"
+require_relative "../../env_config"
 require_relative "../../utils/tty"
 
 File.open("#{File.dirname(__FILE__)}/../../utils/tty.rbi", "w") do |file|
   file.write(<<~RUBY)
     # typed: strict
-    # frozen_string_literal: true
 
     module Tty
   RUBY