[INTPenis]

How do you handle release upgrades?

[notaplumber]

For as long as the release is supported you can use syspatch(8). They also appear to provide serial console access on request so you can perform a release upgrade via the recommended bsd.rd (RAMDISK) kernel method.

There's also the manual upgrade method, for an example of what that looks like, here's the guide for going from 6.2->6.3: https://www.openbsd.org/faq/upgrade63.html#NoInstKern

[INTPenis]

The key here is console access.

I have an OpenBSD router at home and the only negative part is about once every two years when I feel the need to catch up on the latest release.

Because then it needs a null modem cable and direct access.

So when someone is selling remotely managed OpenBSD VMs my natural question is how to do release upgrade.

[sedachv]

You can do unattended upgrades using autoinstall(8). There is a handy script for patching bsd.rd with a configuration file for the update process: https://bitbucket.org/semarie/upobsd/src although there should not be anything to configure on most boxes (maybe you want to deselect the X packages for your router).