Part of the problem with running your own #selfhosted #email server is dealing with spam. I use RBLs and whatnot, but when something gets by, part of the fun is using #Postfix to get creative with the #SMTP transactions. #unexpectedbeatles
Sometimes, if I block an IPv4 subnet, I explicitly tell the spammers that they can try resending their spam over #IPv6. That should help spur adoption and phase out #legacyIP.
@colincogle
If it wasn't for the risk of false positives and the cost, it'd be tempting to feed the spam to an LLM with a suitably hostile prompt and see how long it could keep them talking.
@colincogle (also always fun to see a .name domain in the wild - I co-founded the company that launched them; we actually started as a webmail service, so I had many "fun" moments fighting spam back then)
@vidar Hey, cool! It’s always an adventure to see what sites still think email addresses end in three characters.
@colincogle Yikes. Yeah, we had some "interesting" exchanges with people back then as we were politely pointing this out to people. But back then it was only us, .info, .aero and a couple more (though the other in the first round were also hit by people who used an exhaustive list of 3-letter TLDs) - you'd think people would've learned by now...
@vidar Someone in an MMO once accused me of being a bot, so I played man-in-the-middle with them and M-x doctor (helps to be a fast typist). Had them going for more than five minutes.

@kentenmakto Hah! Probably an even stupider audience, but at one point, spurred on by seeing people interact with channel bots on IRC, I put up one that would *just* repeat one of the same 4-5 bland messages at random every time you messaged it, and while most caught on pretty quickly, a few kept chatting with it. One got into a lengthy "argument" with it over a half-hour period where he got increasingly irate at the repetition.

Of course, people are more used to bots now (this was ~25y ago)

@vidar The audio version of this works really well on telemarketers, especially because unless you cuss at them or say 'put me on your do not <click>' they get in trouble with their bosses if they hang up on you. I heard a recording once that had me in stitches.
@colincogle is that an auto-generated blacklist? I'd never have time to do that by hand, but I'd love to have spamassassin bounce emails with clever burns like this!
@tito_swineflu No, that’s all by hand. I only waste time on serial offenders.
@colincogle I am far too lazy to do that and use an external spam filtering service. They offer personal accounts through which to run one's mail (to get *more* spam to recognise waves, I assume), and I have weaved that into my mail setup and for one of my "clients". Must be done on a per-person basis, though.