Hey, what is your Mac model ? Rosetta 2 is specifically designed for Apple Silicon Macs (M1, M2, M3 series) to run Intel/x86 apps. If you're running an Intel Mac, Rosetta is not supported/needed. For the Rosetta installation, try: softwareupdate --install-rosetta --agree-to-license This command includes the license agreement flag which might help bypass the initial error. If you're still getting the Rosetta installation error, you can check if it's already installed: Go to Applications/Utilities Right-click on Terminal Select "Get Info" Look for "Open using Rosetta" checkbox - if it's there and checked, Rosetta is already installed! For the game-porting-toolkit installation failing due to OpenSSL, here's a workaround solution from https://forums.developer.apple.com/forums/thread/768326 The suggested solution has these steps: First, tap into the rbenv repository and manually install openssl@1.1: brew tap rbenv/tap brew install rbenv/tap/openssl@1.1 Then proceed with the original Game Porting Toolkit installation: brew tap apple/apple http://github.com/apple/homebrew-apple brew -v install apple/apple/game-porting-toolkit This works by getting openssl@1.1 from an alternative source that still maintains it, bypassing the deprecation block in the main Homebrew repository.