Using rvm I upgraded my ruby to 1.9.3-p392, also added 2.0.0, anytime I try to use this version when I run my bundle command I get this error.
Could not load
On macOS 10.14, Ruby 2.5.3, and OpenSSL 1.0.2n this worked for me:
./configure --with-openssl --with-openssl-dir=/usr/local/ssl
but I was only trying what the error messages were telling me:
*** Following extensions are not compiled:
openssl:
Could not be configured. It will not be installed.
/Users/brian/Desktop/Ruby/ruby-2.5.3/ext/openssl/extconf.rb:97: OpenSSL library could not be found. You might want to use --with-openssl-dir= option to specify the prefix where OpenSSL is installed.
Check ext/openssl/mkmf.log for more details.
*** Fix the problems, then remove these directories and try again if you want.
make[1]: *** [note] Error 1