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.
@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.