Well, I’ve been fairly pleased with IHateSpam for Outlook. The reliability is pretty decent, in terms of false positives and false negatives, and both are relatively easy to correct. That takes care of work.
Of course, I get so much fricking spam at work — 20-40 pieces per day — that I’ve given up on submitting it to SpamCop. I just don’t have the hours of the day. That annoys me, but nothing to be done.
On the personal e-mail side, with Outlook Express, I’m shifting gears again. IHateSpam’s OE version is pretty sucky to use, which is largely the fault of OE not being at all extensible. I’m going to give it up, alas.
I’ve had SpamAssassin via HostMatters for some time, but its effectiveness seems annoyingly limited — and tuning it is really irksome.
So now I’m trying POPFile — which sit as a mail proxy between OE and the POP server. I’ve sort of figured out the interface, and have it learning on my machine what’s good, what’s evil. I’ll let you know how it goes.