I know this has been beaten up to death in various forums/lists, but I'd like to share my experiences after my last upgrade (which led to a brand new shining box). portmaster(8) rocks. It makes things look (and be) much simpler than portupgrade(8). I admit, as day(s) passed by with trying the portupgrade way (without success), the thought of going Debian got into me, as time was running short, and I am afraid that hadn't I tried portmaster, that might be the case. I do not say that even with portmaster things went smooth. In fact I haven't got a single smooth ports upgrade in FreeBSD since 2.7 (circa 1997). Two ports multimedia/x264 and net/kdenetwork4 could pretty much act as show stoppers. Nevertheless, and despite that, the whole experience felt much much more solid, and fast. Speed is also a big advantage of portmaster vs portupgrade. Portmaster rocks.