School Admin insists on name-based email address policy, teacher gets unfortunately inappropriate email upsetting parents: 'I went ahead and followed orders'

When I was a wee lad entering into the 6th grade, the middle school I was attending had an unfortunate naming convention for our usernames that consisted of the first five letters of your last name followed by the first three letters of your first name… Naturally, my username was thus "DicksBra." Now, you can imagine how much fun we, a group of 11-year-old boys, had with that. Any time my username was required, it was gleefully announced or entered to the tune of stifled laughter. I'm not sure the responsible adults involved ever realized what the joke was or even would have cared, but surely at some point, a good-humored teacher had a good laugh.

It seems to be a thing that no matter the naming convention for usernames or email addresses your organization adopts, you're going to end with some funny, inappropriate, or downright offensive names. So, as with anything else in life, flexibility is key, but flexibility isn't a trait that school administrators are necessarily known for, which creates problems in certain situations like my own and in the story below.