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What are some of the dumb things you have done with e-mail?

My latest e-mail fail occurred a couple of weeks ago, the day I was leaving for vacation. Somehow in my rush to get an "out-of-office" message into Apple Mail I ended up spamming everyone in my inbox. In a way that I'm still too horrified to truly understand I set up a rule that started to auto-generate e-mails that contained my out-of-office message.  At 5:00 pm, as I was trying to get out the door to pack the car, I started to get messages from people asking why I was sending them multiple messages, all with the same content.  I immediately killed the rule, and then closed Mail, but the command had already been kicked off in Exchange, and my spam kept going and going.

At that point I knew that there was nothing I could do (short of contacting the Exchange administrator), so I took the only logical step available. I left the country. For 10 days I didn't once check e-mail, and by the time I returned most people had forgiven me for sending them all the useless messages.

Does Apple Mail have an easy "out-of-office" feature that I'm just too slow to figure out? Do other people use the "rules" settings in ways that actually work? Is this more proof that the farther one progresses in an academic technology career the dumber one gets?

This is but one example of stupid things that I've done over the years with e-mail. I have a long history of sending messages to the wrong people, accidentally forwarding e-mails that should not have been forwarded, and forgetting to send attachments. I've accidentally deleted messages that I meant to save, and saved messages that should have been deleted. I've tried and failed at being a zero inbox person. Complex message rules and automatic sorting and tagging never work correctly for me. Some people are e-mail gurus, I'm an e-mail amateur.

What about you? Have you ever accidentally sent e-mails to every person on campus? Forwarded private budget or salary information by mistake? Sent an e-mail to the last person you would want that e-mail to find?

What is your biggest e-mail fail?

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