FWIW I am religiously opposed to content-based filtering for exactly
this reason.

I "filter" only with blacklisting and greylisting. Although they can only be done at a boundary mail exchanger, I find it invaluable that there's really no such thing as a false positive; if legitimate mail bounces then
it, well... bounces.

I do all kinds of crazy filtering. Some is content-based, although recently I've been focusing on other criteria. Yes, there have been occasional false-positives; when I find one, I fix it so it doesn't happen again.

I do content-based filtering only after all other filtering options have been exhausted. Messages with a sufficiently high score, I don't bother looking at, and false positives there are nearly zero. Messages with a questionable score, I do check periodically, so any legitimate messages aren't lost, I simply don't see them as quickly as I would if they weren't filtered. I find this situation much less annoying than if I were to turn off content-based filtering altogether.

One thing I haven't set up yet is greylisting. It sounds very effective, but I have some users that depend on being able to receive an e-mail immediately (e.g. while they're on the phone with the sender), and get quite annoyed when there's a significant delay. I know, that's not how e-mail is supposed to work, but who am I to tell them that? Still, I do want to do greylisting in certain cases; I just haven't gotten around to setting it up yet.

Ugh, I hate spam.

~ Andy

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