If you'd like to update the keg-only OpenSSL brew on osx, and dont care for legacy and crap:

     ( export CONFIGURE_OPTS='no-hw no-rdrand \
       no-sctp no-md4 no-mdc2 no-rc4 no-fips no-engine'; \
  brew install https://gist.github.com/steakknife/8228264/raw/openssl.rb )

Beware, that by default on osx/ios, pretty much everything links to sketchy CommonCrypto or a crusty, quasi-deprecated 0.9.8.