Updating OpenSSL and Ruby in Passenger/Apache Setup

[Jonathan Hilgeman]

I have an interesting situation where I have a server running a large, 3rd party application that was built against Ruby 1.8 with Passenger 3.0.1 + Apache 2 and OpenSSL 0.98o. Bottom line - I don't manage the 3rd party app and updates are very difficult and cumbersome to put into place. 

Now, there's a smaller, custom Ruby app that was developed internally by an employee who ended up leaving, and he developed it on the same platform and plugged it into the existing infrastructure. I now need to update this custom application's crypto capabilities. To avoid impacting the main, 3rd party app, this means running a separate, updated copies of OpenSSL (1.0.2l) and Ruby (2.4.1) on the server. I already have these 2 updated components in place at:

/usr/local/openssl/1.0.2l

/usr/local/ruby/2.4.1

When I install Passenger via gem, I get version 5.1.7. I'm trying to figure out how I can allow the old, existing stack (with Passenger 3.x) to continue handling the existing 3rd party app using Ruby 1.8, while our internal, custom application gets executed against the Ruby 2.4.1 stack.

When I try to install Passenger 5.x via the standard steps (passenger-install-apache2-module), it picks up the old copy of OpenSSL (0.9.8) and then hits an error during the install process. I tried setting CPPFLAGS and LDFLAGS to point to the newer OpenSSL library:

env CPPFLAGS='-I/usr/local/openssl/1.0.2l/include' LDFLAGS='-L/usr/local/openssl/1.0.2l/lib/' /usr/local/ruby/2.4.1/bin/passenger-install-apache2-module

...but the flags don't seem to be respected by the installer. 

To be honest, I don't even know if I absolutely need to update Passenger or not in order to accomplish my goal. Can anyone provide some general guidance here?

UPDATE:

I've now seen that the proper flags are "EXTRA_CXXFLAGS", "EXTRA_CFLAGS", and "EXTRA_LDFLAGS".