I discovered that I can successfully install ruby with any of the following commands:
$ rvm reinstall 1.9.3-p327
$ rvm reinstall 1.9.3-p327 --with-openssl-di
How about:
ruby -ropenssl -e "puts OpenSSL::VERSION"
Ruby has quite complicated mechanisms for detecting libraries, every extension has it's own code for that. Fortunately most of the extensions support pkg-config so it's possible to force location of *.pc files:
PKG_CONFIG_PATH=/path/to/openssl/lib/pkgconfig rvm reinstall 1.9.3
rvm use 1.9.3
then after compilation you can verify on OSX:
find $MY_RUBY_HOME -name openssl.bundle | xargs otool -L
or on linux:
find $MY_RUBY_HOME -name openssl.so | xargs ldd
as for the --with-openssl-dir=... it is not fully supported by ruby, it should be --with-opt-dir=... + --with-openssl, opt-dir supports multiple paths separated with : starting from ruby 1.9.3-p327