Monitoring the Email Monitor was originally published on November 21, 2007.

“Ummm…” the top email in Alex M.’s inbox started, “why did you delete my message about the approval bug? And then delete the message inquiring about the deletion? This issue isn’t going away – please investigate this right away!”

Had this been the first like message Alex had seen, he might have been surprised. But it wasn’t. For the past several weeks, customers, vendors, coworkers, and anyone else who emailed him received some rather interesting status notifications regarding their message. It was seemingly random and consisted of replies like “your message was deleted without being read,” “your meeting request has been declined,” or even “I will be out of office for the rest of the day.”

As he had gotten used to, Alex replied back. Sorry, I’m actually just reading your first email now. We have been experiencing some strange email glitches as of late, but I can assure you, I’m working on the issue right now.

It was a partial truth. While strange, random replies were certainly being sent in reply to emails, it was not the fault of any server or email software. The real culprit was The President.

A few weeks prior, The President of Alex’s company – a small ERP software company – decided that there was simply too much risk in having unmonitored email. Someone might speak badly of him or, worse, slander The Company! Being the somewhat tech-savvy guy that he was, The President covertly called up their email service provider and asked them to copy every incoming or outgoing email message into a mailbox discretely called TRASH11. No one – not even those pesky network admins – would ever figure that out.

This particular decision led to a direct collision with another one of The President’s recent decisions: all email clients shall automatically send read, delete, and any other sort of receipt that the sender requested. If The President sent someone an email, he wanted to know exactly when his message was read. And of course, since this policy applied to him and his TRASH11 mailbox as well, The President’s monitoring activities would trigger these status notifications to be sent out.

It didn’t take too long for those pesky network admins to learn about the TRASH11 mailbox. Within a few days of receiving a copy of every single incoming and outgoing message, TRASH11 grew to be gigantic and triggered a “disk space quota warning” to the network admins. Of course, The President saw this message in his TRASH11 mailbox and promptly called the email provider to request a larger size limit.

It didn’t take too long for the software developers to figure it out, either. Their messages would often get two read receipts: one from the actual recipient and one from TRASH11. And sometimes, TRASH11 would delete their messages without reading them. The spurts of receipts – often 10, 20 at a time – made it pretty clear that someone was snooping on their messages.

As the weeks progressed, both developers and network admins complained to the IT Director about the communication problems this was causing, and the IT Director eventually confronted The President about it. Shortly thereafter, The President sent out an explanation: I apologize for any glitches that might have been occurring with email receipts. I wanted to be able to read my email from home and had a mailbox created just for this purpose. For whatever reason, this caused all sorts of receipts to be sent out from TRASH11. The problem should be fixed, however.

Now, had the majority of The Company’s employees not been software developers or network administrators, or didn’t write their own mail server in the past, or even didn’t have access to the email system changelog (especially the entry that started “The President requested TRASH11 be created to forward…”), The President’s explanation might have been believed. But of course, all of these were the case, so the employees just shook their head in amazement and let The President carry on with his TRASH11 mailbox.

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