My first job had a coworker who didn't know how to sort the spreadsheet. She printed it out and cut it into strips, then sorted them while watching TV at home in the evening, then taped it back together. I was shocked and in the decade or so after that I have yet to run into anything like that again.
My introduction to Office/office horror was a colleague writing her message in PowerPoint, attaching it to an email in Outlook and sending it through.
It turned out to be a standard practice in the academic institution I was in.
Not quite the same, but in several community email lists, sending emails via a JPG or DOCX is the norm. Type it up in Word, and attach it to the email.
My institution's administration does this. Every message from them is typed in Word, then attached to an email whose body says "Please read the attached message". They do this for every message, no matter how trivial.
I asked them why they do this, but haven't received a reply, perhaps because my question was in an attached gzipped Postscript document.
