Version in ports r8.2 is from 2020-02-14. Latest version of security/openssh-portable is 8.4 version was published 2020-09-27 https://www.openssh.com/txt/release-8.4 8.4 (and 8.3) have quite a few fixes/features for FIDO use cases. There is also a few fixed security issues.
Sorry, for being a bit off-topic: The version in base also needs an update! OpenSSH_7.9p1 :-(
Tagging in emaste in case he's interested; he's briefly taken over OpenSSH in base, I'm not sure if maybe there's something that would be related+useful with openssh-portable from his perspective.
Working on this now
A commit references this bug: Author: bdrewery Date: Mon Nov 16 19:39:35 UTC 2020 New revision: 555512 URL: https://svnweb.freebsd.org/changeset/ports/555512 Log: - Update to 8.4p1 (skipped 8.3) - https://www.openssh.com/txt/release-8.3 - https://www.openssh.com/txt/release-8.4 PR: 239807, 250319 Sponsored by: Dell EMC Changes: head/security/openssh-portable/Makefile head/security/openssh-portable/distinfo head/security/openssh-portable/files/extra-patch-hpn head/security/openssh-portable/files/patch-ssh-agent.c