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I have my website hosted at one location, on a server that also accepts email, and I use Google Apps for mail as my email provider. I've had no problems in the last 18 months, and no reports of email being lost.

This week however, someone using Hotmail has tried emailing me. 25-50% of the emails they send are returned to them, with a "550 relay not permitted" message.

My MX records are correct, and checking the Exim logs on my web server I see that Hotmail is trying to send emails to the A record, because this server can accept email. This appears to be a known problem with Hotmail.

As I can't disable the webserver from accepting mail from Hotmail (since other people use the web server as their email hosting), is there a solution?

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You should provide the domain in the future so we can directly look at the issue. – citadelgrad Aug 4 '10 at 15:10
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3 Answers

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Hotmail fails to use proper DNS rules. Hotmail will always try to deliver to the domain's A-record first and will ignore MX-records. If the domain A-record accepts a connection (eg. it runs a mailserver) it will try to deliver the email, which in most cases will not be an issue if the webserver and mail server are the same box.

However, if an domain uses a different mailserver Hotmail will still try to deliver mail to the domain's A-record. If the machine gives a 550 Relay denied Hotmail will fail to deliver the mail. It does NOT try the domain's MX-record.

THe only work around is to firewall port 25, so Hotmail is unable to connect to your port 25. If that fails hotmail will try to resolve the MX-records.

This has been an issue for years, but Hotmail is ignorant.

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Do you have any references for this? It doesn't sound right at all. – Dan Jan 13 at 13:26
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@Dan windowslivehelp.com/… Doesn't sound right, but that's what they do. – sam Jan 13 at 15:05
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up vote 3 down vote

Are you sure that your MX records themselves work consistently?

If for some reason Hotmail can't look up your MX records but can look up your A records, they'll try the latter.

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Hmm, all the online services I tested were correct. However, pinging my nameservers, it turns out that the first server had disappeared offline and was no longer resolving - looks like I need a more reliable DNS provider. I've updated this and suspect it'll now work as expected. – PeterB Aug 4 '10 at 9:00
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up vote 0 down vote

The MX-records work fine. Trust me, this is a bug with Hotmail.

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