I submitted Pull Requests to update MacPorts' LibreSSL to 4.4.1 here:

https://github.com/macports/macports-ports/pull/36607

Continuous integration checks passed!

And libressl-devel to 4.4.1 here:

https://github.com/macports/macports-ports/pull/36608

One CI check passed, the other one is queued (though I am guessing it will probably pass as well, barring issues with the build bots).

It's up to someone else with commit access to merge those!

From the release notes [https://ftp.openbsd.org/pub/OpenBSD/LibreSSL/libressl-4.4.1-relnotes.txt]:

"It includes the following changes from LibreSSL 4.4.0:

• Security fix
• Fix an out of bounds read that may happen during renegotiation in TLSv1.2.
• Reliability fix
• Fix TLS interoperability with peers sending more than 32 signature