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I'm hoping someone here has an idea of where to look next. We have a domain we support which has email sent to it from one particular user bounce with the following message:

Delivery to the following recipient failed permanently:

USERNAME@princetonscoop.com

Technical details of permanent failure: Google tried to deliver your message, but it was rejected by the recipient domain. We recommend contacting the other email provider for further information about the cause of this error. The error that the other server returned was: 550 550 Unrouteable address (state 14).

We only have reports of bouncing form this one particular user (who is someone we don't support - except they'd like to be able to contact our customer and we're trying to figure out if the problem is on our end). Many people can successfully send to this domain and the user who is getting bounce messages can send to other domains that we support (so it's clearly something specific with the princetonscoop.com domain and not our setup in general). I've reviewed the MX records multiple times and the server logs don't show a connection which generates this error (in fact this error is not one that our mail server would ever return). So it appears that google is contacting a different mail server for some reason. I have tested sending from my gmail account and that works. I believe the sender is using a google-apps account (the account they are using is from their own domain, not a gmail account).

Any ideas on what might be happening here or what to test/investigate next? Thanks.

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2 Answers 2

This is a rejection from the receiving mail server, so you would need to get with the mail admin for princetonscoop.com and have them look at their logs. Many anti-spam filters don't give you more info than what you have in your bounce message, so it could very well be bouncing because the sender is in an RBL or other SPAM database.
You have tested all that you are able to at this point, so you need to get some help from the mail admin at princetonscoop.com. Good luck!

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I was probably unclear above. We we are the admins of the princetonscoop.com mail server (but not their website - which turns out to be important - see the solution below), and the bounce message we're seeing isn't from our servers (and there is nothing in the logs that indicates that delivery was even attempted on the message that bounced). –  user45239 Jun 21 '10 at 18:34

So a key piece of the puzzle is that the websites for both of these domains (princetonscoop.com - the domain we support, and janeconsignment.com - the domain we don't support and who cannot email princetonscoop.com) are hosted on Media Temple. I'm not sure exactly how email is setup for janeconsignment.com (since they aren't our client) but I believe they are using Google Mail for their domain. Media Temple does a pretty standard thing and bypasses the DNS lookup if the email is sent to a domain it supports. There's a setting in the control panel that must be set if your website is on Media Temple but not your email server. Since we were not supporting their website, we didn't have access to the control panel and couldn't look around to find the setting. After some more research we figured out they were both with MT, we hunted down some information and asked their web master to check into the setting. Changing the setting solved the problem and the mystery.

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