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

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