If this is the case with libressl, and openssl is just a shim on openssl3, can the dependency in python312 port be changed to openssl3 explicitly? I do have both libressl and openssl3 installed and active.
This of course could be considered, but not its likely not an entirely trivial change.
The reason being openssl3 uses a custom install prefix for its installation, /opt/local/libexec/openssl3/, and does not by default put anything in the primary /opt/local/lib install area. This is how it is able to be installed along side libressl (and openssl2) without conflicts. The openssl port then just depends on openssl3 and adds some shims (aka sym-links) into the primary prefix so ports that depend on it are unaware of this custom install area. This is what makes openssl conflict with libressl as they both provide the same files.
Transitioning a port to depend on openssl3 instead of the shim port openssl then implies reconfiguring the port build to know where to look for openssl3, and how easy this is depends on the port and the build system it uses. The PortGroup 'openssl' exists specifically to make this a bit easier, but its not perfect.
So in short, yes, it could in theory be done but someone will need to do the leg work to change python312 to directly use openssl3 instead of openssl and ensure it works correctly with that change.
If you want this to happen the best way that can be done is to do the legwork yourself and then open a PR with the proposed change. If you are not willing/able to do this, then at least open a port enhancement trac ticket.
