Today's classic.
"You told me email was working. I've got a really urgent email. I sent it yesterday. You told me it had been delivered. This is for an urgent approval. Why has it not been received?"
Continue the tirade until you get bored...
Well, I checked the email I sent that in fact says "email is flowing again" (stuck IIS Admin service on my smarthost). Nowhere do I say the email was delivered. So I check the queue. Sure enough there are 2 emails on retry. So I check the address for delivery. Then I check the email address she wants to contact. Very similar, but there is a typo in the address. The domain typed in does not have a mail server. The domain she wanted does.
I explain this to said user along the lines (and I was polite AND subtle!) of "Can you confirm that you wish to send to domain and not domaan?". User checks with colleague. Grim realisation sets in.
Apology presumably coming by email to me but currently mispelled???
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