This would be nice indeed. I have a small gem that collects information about the
host-system (on the target computer platform; usually linux) available, and notifies
when there are more recent versions of a software available, e. g. a new gcc release,
a new m4 release, a new bison release and so forth.
I am a bit wary of upgrading openssl from openssl-1.1.0i to openssl-1.1.1 mostly
because I am never absolutely sure how well a more recent openssl may work on ruby.
And the primary reason for me to use openssl (and have ruby support it, too) is so
that I can push new gem releases of my code, actually. This was also a major reason
why I used to open issues about both openssl and readline, and I think it was nobu
who then added the "+" commandline flag to configure, to allow compilation to proceed
only if all that has been wanted, been found too (as otherwise I may have to re-compile
ruby or at the least work on this in the ext/ subdirectory, such as for readline or
openssl or zlib).
So naturally, I think it would be nice if more recent openssl versions could be
supported on the ruby 2.5.x branch too, if this will retain backwards-compatible
behaviour.
Having said that, I think after x-mas, I will be using ruby 2.6.x so it would not
be of a massive benefit to me personally.
On a side note, if it were possible, it may be helpful to notify on the ruby-doc
website which versions of a particular software is supported.
Take:
https://ruby-doc.org/stdlib/libdoc/openssl/rdoc/OpenSSL.html
This page could list which version is compatible - or at the least has
been tested. I don't know of a good way to have this automatically for
all versions, but I think it may be useful for quite a few people. (Openssl,
zlib and Readline are usually what I need to have in the local ruby version,
since it is very convenient or necessary for other things.)
I think naruse is in charge of handling both 2.6.x and 2.5.x release so perhaps
he should be asked.