My best automating stuff story, though, is automating complaint letters to UK banks. We were pushing the limits of what the UK's Direct Debit system can handle, and as a result were seeing all the edge cases where banks got it wrong. One common one was banks accidentally charging back a payment twice, and each bank had their own, totally bespoke complaints procedure for getting in touch when that happened.
A couple of engineers and me spent a couple of days integrating with Lob and a fax provider whose name I forget to automatically write complaint letters every time the banks screwed up. Some of these were being sent to named individuals for all Direct Debit complaints related to RBS, for example.
Needless to say, the banks fixed the problems that were causing us to need to complain soon enough. :-)