I worked as an office assistant in a small company during my gap year. The boss sent an email to me by mistake, meant for his business partner, talking about a menial task and that he'd "get the monkey to do it". Me. I'd been there over 6 months, I was mortified.
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When I was an administrative assistant, one of the directors accidentally sent me the agenda of the meeting at which they were discussing laying off several staff members, including me.
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A very professional cover letter ... signed "Sincerely yours, bitchesss!" -- clearly a draft they had shared with friends then sent on accidentally without doing a final check.

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that's kind of amazing
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Someone wrote a complaint letter asking for a refund on flight tickets. Included with various tickets, receipts and a FURIOUS letter, was a cycling proficiency certificate.
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that is priceless
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Not me personally but an error by Tesla saw my boss taking them to court. They accidentally revealed a nefarious plan.
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wait... what?
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