Upgrading OpenBSD

I have an amd64 system running 6.8. It doesn’t do anything unusual – I am using it as a normal desktop client with Firefox and Thunderbird. This morning I ran sysupgrade (as root), and it downloaded the 6.9 sets, said it was upgrading, and then rebooted.

After the reboot, I logged in and was greeted with:

OpenBSD 6.8 (GENERIC.MP) #5: Mon Feb 22 04:36:10 MST 2021

Running dmesg and uname also show 6.8:

# dmesg | head -n 2 
OpenBSD 6.8 (GENERIC.MP) #98: Sun Oct  4 18:13:26 MDT 2020
    deraadt@amd64.openbsd.org:/usr/src/sys/arch/amd64/compile/GENERIC.MP

# uname -r
6.8

I spent a lot of time trying to figure out what was going on without any success. I couldn’t find any messages in the logs that provided any hint that an upgrade had even been attempted, let alone failed. Any time I would connect a monitor to capture the actual process the upgrade would succeed.

I finally realised that this machine was the only one that I was upgrading headlessly - I was upgrading everything else with a monitor connected. Perhaps a solution to this would be to buy dummy HDMI plugs that would present a load to the machine, thus tricking it into thinking there is a monitor connected.