[milcron]

I don't operate a server farm but OpenBSD updates are pretty easy. Just do `pkg_add -Uu`.

If your dependencies are minimal, keeping OpenBSD up-to-date is actually pretty relaxing. Don't need to install security patches all the time as with Linux.

[countingteeth]

pkg_add -Uu won't address a single update under https://www.openbsd.org/errata.html , i.e. the very most important ones.

Also as far as I know pkg_add still doesn't know about restarting services, so vulnerable processes will be left running.