I run a lot of pfSense boxes. Four updated so far from 2.7.2 to 2.8.0
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Quite a smooth ride so far.
A bare bones job worked fine (new router for a new site for a customer). Then I did my home jobbie with quite a lot of stuff on it. I did de-install pfBlocker-NG first and put it back - all good.
Work: CARP cluster - two nodes (I don't care if you don't like the terminology - you know what I mean). I'm external! Took a config backup of both nodes. It late and I have a downtime scheduled.
Updated the secondary and the update count out never finished. I always run a ping and simply reconnected manually.
Put the primary node into persistent maint. A lot of things were not available but I ploughed on. I'm at home so external so there is a good chance I was not testing effectively. Besides, fiddling around is downtime.
The primary came back up and all good so far. I'm not going to dwell too much because I am external to the site but it looked like all CARP/HA etc stuff failed to work whilst the cluster was part way through the upgrade. That's not the normal experience but again, I'm not absolutely certain yet.
Both nodes run pfBlocker-NG and I did not uninstall it first or any other packages.
These are pretty complicated with a lot of NICs, VLANs, OpenVPN, IPSEC, FRR, pfBlocker-NG, HA Proxy, ACME.
All good 8)