@mathew @fanf Wait, I just noticed something extremely damning in those packets. It's trying to talk to port 25 on the remote server, not port 587. That's got to be wrong, and somehow it's got to be my fault, though I don't know what I did that would cause it. But this feels like something that should be solvable.
[EDITED to add:] No, I'm a moron, and the initial SMTP connection is meant to be on port 25. Right? I am so ignorant. I will try it with Python smtplib again and watch exactly what it does.
[EDITED again:] Nope, Python/smtplib connects on port 587 right from the start and never attempts port 25. This must be what's broken.
[EDITED a last time:] Aaaand the ghastly hack of adding "port = 587" to the smtp smarthost section of my Exim configuration makes it work again. I suspect I should be doing something less ghastly. I still don't know what made this break.
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