Yesterday I thought I'd have good time to update my firewall OS pfSense from version 2.0.3 to the latest 2.1 using automatic update. Worked plenty of times, especially when going between stable versions. This time though, not so much.
After initiating automatic update, everything was going well. Downloaded, installed and rebooted. I was just wondering how long it would take to bring the web based GUI back online. A quick dive through VMWare vSphere console told me that the re-installation of packages is still going on and I shouldn't worry. Except I knew that GUI is up before re-installation starts, so what the hell is taking so long?
After restarting the GUI I notice that the process was not running, so maybe a hitch? Restarting didn't help though and the new version does not seem to have "reset" option for GUI, only login reset. Useful as fuck this. Digging up the logs shows me that the root certificate for the HTTPS can't be found, apparently the update either changed something or failed to create it. Swell and no change to go back to HTTP to fix this.
Luckily I manage to dig the PEM certificate out of config files, save it to the server via console and I have GUI access again. The best version of pfSense (now with IPv6 support, I shit you not) had the worst start. But we made up already.