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The issue here is one of an email that has been "lost in cyberspace." The receiver is claiming never to have received it. However, I recieved an automated out-of-office reply as a response to my email. They are now saying that my original message never even landed in the recipient's inbox since the mail server's spam system must have blocked it.

It seems odd to me that a mail server would allow such an out-of-office reply to a message that it at the same time deems to be spam. Is this a correct assumption?

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The vacation message should be enough to show it got out of your zone of control; if the recipient's MTA ate it, that's something for the recipient to take up with their admins. – womble Jul 25 '11 at 6:12
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Assuming they're running Exchange: If you got an OOO reply then it got to their Inbox.

If they're running another system: It would depend on whether their OOO system is before or after their spam filters (but I have never seen an OOO reply system before the spam filters, that would make using their MX as a backscatter source trivial).

Without knowing more detail, I'm comfortable calling BS on them.

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Chris, thanks so much. This is exactly what I thought. I was not sure however if it was possible for the spam filter to kick-in after the OOO (did, however, not seem logical to me). What would be the best way to determine whether they are using an Exchange server? I do know for certain that email clients on the server use the MS Outlook web application to access their email accounts – James Jul 24 '11 at 21:14
@James; telnet their.mail.server 25 and the response will be something very similar to 220 their.mail.server Microsoft ESMTP Version XYZ... if it's Exchange – Chris S♦ Jul 24 '11 at 23:12
Also, in the future, for anything that's important, send your e-mail with "Request Delivery Confirmation". Almost all e-mail servers are configured to comply with the request, then you'll get a response from the server saying it was delivered. – Chris S♦ Jul 24 '11 at 23:14
For values of "Almost all" that equal "only the very enterprisey"... – womble Jul 25 '11 at 6:11
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