Oh, the memories
In $former_job in commercial web hosting, customers had the ability to create simple mailing lists. One of them ran a mailing list for a large, disparate charity organisation - and also ran several of said organisation's branch mail systems.
For some unknown (still) reason, they used Microsoft's SBS product with the dumbest POP3 receiver code I ever saw. The following happened:
1. Mail gets sent to list
2. Mail gets expanded to recipients
3. Mail goes to one of the aforementioned SBS POP3 connector widget, which looks at the incoming message and thinks 'this isn't for one of my addresses, it's been sent to some-list@some-domain...'
4. SBS POP3 widget sends message to mailing list
5. GOTO 1.
The list had thousands of subscribers. I lost count how many of these SBS machines were involved - at least 4 - but the resulting storm saw our customer attempt to claim £250k in damages from us for lost business! The last I knew about it, they'd backed down and as far as I know it never got to court.
Hilarious at the time, but the aftermath was bloody irritating.