554 Relay rejected for policy reasons

Microsoft Exchange
A user was communicating with a contact(external email address). He was able to send an email to him but when he replied to his contact's email he got a delivery failure report. That report is pointing "554 Relay rejected for policy reasons" as the cause. Could you help me understand this delivery failure report? We're currently using clearswift on our network. Thanks in advance

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Oh, congratulations. The recipient system is blocking you, possibly because your email meets THEIR spam criteria or because your IP (or ISP) is on a blacklist. You need to talk to their IT to find out exactly what their issue is.

Now, am I reading correctly that an email originating with your user goes through, but a reply does not? This could mean that they are reading the email or its format incorrectly. But either way, the problem is the way they are seeing these emails. I’ve had this problem before. Talk to the IT folks at the recipient company or ISP. The problem is on their end.

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  • Bobkberg
    Another possibility is that they are "gray-listing" and they haven't done it correctly. IF that is the case (no actual clue here)... Their mail server should wait until your mail server attempts a re-send, and then accept the message. The theory behind gray-listing (grey-listing if you're British) is that spammers don't bother with re-transmissions after some period. But if not implemented correctly, it can bounce things that the admins did not mean to bounce. Bob
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  • Jlnewmark
    I replied privately to Chakazukin, but thought I'd also post this in case it helps someone else: The message specifically says it thinks you are *relaying.* This could mean that it's not seeing replies correctly, or that something about that reply looks like it's coming from a different domain than the one in your email address. Again, you'd probably have to talk to their IT department -- it still sounds like a misconfiguration on their side.
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  • Drahcster
    A couple of questions... 1.) What mail server are you using on your network? 2.) What mail client? 3.) Does the user access mail through POP3 or IMAP4 or does he have a direct connection to the Exchange Server?
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