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I find it quite annoying that I have to have a monitor plugged in for the upgrade to work. Otherwise it reboots into the old version after downloading. Is this a common problem?

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I have a similar issue, my router won’t reboot without a monitor plugged in to the hdmi port. Displayport worked fine during the installation. It was clever enough to not work with a dummy hdmi dongle either.

I have seen it, upgrades use a cut down kernel (bsd.rd) which doesn’t have the same graphics drivers.

You may find setting the console to serial works around it (set tty com0 in /etc/boot.conf).

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