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It's a lot easier these days with the new pkg tools.

I've used the new pkg tools a little. Can you be more specific? Can they be used to reliably apply unattended security updates now?

There days people use freebsd-update to do this. http://serverfault.com/a/738217/41952

Accompanies with ZFS boot environments there's literally minimal fuss about upgrading and worrying about possible breakages.

Thanks, I hadn't seen `freebsd-update install --not-running-from-cron`. I'll give that a try.