Ok, so the CheckSSL script is definitely not finding openssl. The extensions requires a version newer than 1.0.1, but since brew only ships OpenSSL 1.1 and 3.x I think we can rule out an older version. Can you confirm which version of OpenSSL is installed?
One reason why we may fail to find OpenSSL could be that pkg-config is missing. Could you please check if the pkgconf brew package is installed? You can do so by running brew list | grep pkgconf. If it’s not listed, please install it and try again. If this turns out to be the cause, I can then see what we can improve on detecting OpenSSL installed through brew; I’d hate to hardcode a path.