For the past six months or so, I have been fighting with homebrew, rvm and openssl. I frequently am unable to run "gem install XX" getting the error: "Unable to require openssl, install OpenSSL and rebuild ruby (preferred) or use non-HTTPS sources".
I installed openssl with brew ("brew install openssl") and had to set the LDFLAGS and CPPFLAGS. That got it working. However, when I ran 'rvm requirements', rvm installed a different version of openssl and now everything is broken. I tried running 'rvmreinstall 2.4.1 --with-openssl-dir=/usr/local/opt/openssl' but that throws the following error: "Error running '_rvmmake -j 1',".
I am sure this looks like an rvm issue, but I am placing this here because it appears homebrew and rvm want to require different versions of openssl and the two requirements are conflicting.
Any one else dealing with this problem?
I am on a Mac using Sierra (10.12.4) with up-to-date versions of homebrew and rvm.