Years ago, I had recently graduated from college and was working at two part-time gigs. My morning job was at a small financial company as the sole IT guy.
This small financial company was a child company of a much larger and more famous parent company based in New York. We were allowed to use whatever software we wished, with a few exceptions dictated by the parent company. One of these exceptions was our email software: We were ordered to use a relatively obscure email software made by a famous company.
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I had never used this piece of software before and found many quirks, which made it annoyingly different from more widely used options such as Microsoft Outlook. In my frequent dealings regarding this obscure email software with the parent company's tech support department, it became clear that no one enjoyed using it and were entirely aware of its many unfixed glitches.
On my birthday, I went to my morning job and the head of HR called me over to her office to inform me that a woman in our office -- we'll call her "Jennifer" -- was being laid off that day. I was instructed to go to Jennifer's computer and set her out-of-office email message alerting those who emailed her in the future that she was no longer with the company.
I waited until Jennifer had left the building, then logged in to her workstation, opened the obscure email software, and set her out-of-office start date and stop date, as well as the out-of-office message. Next, I clicked OK. I then reset her password and went through all the other steps of closing down her workstation.
I went back to my desk and started preparing to leave for my birthday lunch. A coworker came up to me and said he had just received an email from Jennifer saying she was no longer with the company. I told him that the email was correct and that the message was going to be sent to anyone who emailed Jennifer in the future. However, he said that he had not emailed Jennifer that day, and as he described what happened I noticed he had received the email as soon as I had set her out-of-office message.