We will need to address those gems for 9.4 but this is okay for now. Ruby 2.6 does not use those libraries as gems anyway. Could you open a few issues on jruby and those libraries to get the process moving?

Have these changes been merged into Ruby 2.6? We generally try to match their standard library exactly and not go beyond it.

changes like ruby/net-smtp#4 ruby/net-smtp#21 were already merged, but they weren't backported to 2.6.

here's a ruby ticket that tracks the promotion to bundled gems https://bugs.ruby-lang.org/issues/17873

not go beyond it.

I have to admit there's a compatibility concern here, even if I didn't found any issue that could break puma or something like that. We should probably wait with this until JRuby 9.4, but the good part is we know what works, what's missing, and what needs to be done to make this happen.

Could you open a few issues on JRuby and those libraries to get the process moving?

there are already open issues
1/ jOpenSSL APIs, jruby/jruby-openssl#112
2/ Digest, ruby/digest#20
3/ SSLSocket#session=, and there's also this change 12082fd

and release all gems (I think it won't happen before the Ruby 3.1 release, but maybe Ruby maintainers will be willing to do so sooner)

I'm really looking forward to finally address http://blog.headius.com/2008/02/ruby-threadraise-threadkill-timeoutrb.html after 13 years :)

Agreed on all points, thanks for the links to the key open issues. We will get 9.2.18 out today, then wrap up 9.3 by end of month, and then start the heavy lifting to bring 9.4 in line with Ruby 3.0 including these troublesome gems.

There is a mild update of net libraries in #6802, to align them with Ruby 2.6.8.