I have a cron job that fires off a Perl script at 8:45 a.m. every Monday morning that composes that e-mail and sends it off for me.
On the rare occasion that I was on vacation the previous week (and forgot to disable it), I just text our payroll lady and tell her to "ignore that e-mail, I was on vacation last week".
She knows it's automated and she doesn't care. She's required to receive an e-mail from me before she pays me and that satisfies her requirements. The boss knows too, he just shook his head and laughed when I told him about it.
It sorta reminds me of how, when a "measure productivity by number of tickets closed" policy gets enacted, everyone just starts creating tickets for every menial thing they do.
My second favorite is the one that runs once an hour, deleting any IP addressing / DHCP lease / similar data older than 24 hours (I work for an ISP).
Sorry, IP-Echelon, the company policy (which I wrote and enacted) says we don't keep that (IP <-> User) data for more than a day, so I can't "ensure the user and/or IP address owner refrains from future use and sharing" because I don't know and can't tell who it was.