To provide more details on my situation: I am connected via ssh. I launch sysupgrade. It creates the filesets in /home/_sysupgrade and it creates /boot.upgrade
Then it reboots, all filesets are deleted, but the system is still on the older openbsd, as evidenced by “uname -r” I have 2 ssds each running openbsd, but the UEFI is clearly specified to boot against one of the SSDs. Maybe it’s not booting correctly against /boot.upgrade? I can do “sysupgrade -n” and then instead of “reboot”, can i boot explictely against “\boot.upgrade”? Thanks > On 25 Dec 2025, at 13:40, Hide My Email <[email protected]> wrote: > > Hi all, > > I have a weird situation. I am upgrading an old system that was on 7.5. > > I upgraded 7.5 -> 7.6, then 7.6 -> 7.7 and now 7.7 -> 7.8. > > I ssh into the machine and run sysupgrade. > > When I give it 5 minutes, and then ssh back to it, the upgrade has not been > applied. > > However, if I connect a physical screen to the computer (via HDMI), and then > launch sysupgrade via ssh (the same thing), then the upgrade works. > > That makes no sense to me, but I've consistently seen that happening three > times now. > > Does anyone have an idea of what I should look into? > > Thanks

