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This is a strange problem. We are using an Exchange 2007 server to handle the emails to and from the company. There are two main problems which are probably related.

  1. None of our mails sent to one single customer are ever received.

When we send any type of mail to one particular customer, they never get it. We have confirmed the address and tried to send more to other mail addresses on the same domain and they still don't receive it. No error (email or otherwise) is ever issued. (Domain related? Blacklisted?)

  1. Sometimes (intermittently) a mail sent to our company (can be any address on our domain) is never received.

I tried this the other day from home and sent a mail to my work address. It was never received. But then a day later i sent another and it was received fine (so the mail address is fine). No error (email or otherwise) is ever issued.

Any ideas where to start looking for causes?

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up vote 2 down vote accepted

If you're going to track this problem down, you have to start by looking at the message tracking logs on your Exchange server to determine exactly what YOU did with the message. If you're not familiar with message tracking in Exchange 2007, take a look at this series of articles that explain how to do it. Send a test message and then track it in your system - you'll be able to determine exactly what your server did with the message. If you see that your server handed the message off to the recipient server, you can relax and be totally confident that your system is working correctly and the recipient server is the one having problems - and you obviously can't fix that. Without tracking the message, you'll have no idea where the actual breakdown is.

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Ok, that sucks. One note to start - MANY anti spam systems just destroy the email. Period. No notification, no error. Just disappears - this is to make sure you can not deduct inforamtion about email addresses from the rejection.

I would check that single customer by runnin a trace on some emails. Check your SPF record if you have one (and put one in if not) - SPF fail is a tapicaly limited issue: those who check SPF throw the email away, most servers don't heck yet.

Can it be you have DNS issues? Connectivitty issues? At times?

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