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Re:PfSense 2.2-Release Now Available by peckrob on Tuesday January 27, 2015 @03:18PM (#8955507)
Weird. Other than the startup thing (which is not a big deal for me because I leave it running), I haven't had any problems upgrading. A few months ago I went to 2.1.5 and pretty much everything just worked.
Re:PfSense 2.2-Release Now Available by organsnyder on Tuesday January 27, 2015 @04:55PM (#8956267)
Minor upgrades were fine. It was a major one (2.0 to 2.1) that wiped it out for me. This was on the embedded version of pfSense - the full version might behave differently.

Otherwise, the upgrade was one of the smoothest I've ever had for this sort of thing.