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Plesk mail server can't send to Hotmail

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Last Modified: 2008-04-24
I'm having a serious problem with some of our domains.

We have a Plesk box, running on Linux, with about 20 domains on it. One of them belongs to a guy who does fairly regular bulk e-mails to promote his band. They're usually sent to the 250-350 people who are on his mailing list.

Unfortunately, none of these messages are getting through to Hotmail. I've had him try sending individual messages to Hotmail users, and it's the same problem.

I'm willing to try anything, however, please keep in mind that I'm not super fluent with Linux or with e-mail stuff, so it may take me a bit of time to figure out what you're saying if you say something cryptic regarding e-mail protocols or something! lol

I've read a lot of stuff on forums recently talking about how Hotmail has changed their spam filtering, and lots of mail servers are being blocked, but no specific responses on how to fix it.

Any help is appreciated!
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Commented:
You can try sending me an email at test@cdlive.co.uk (post here when you have sent it) and I will see if there are any problems.
However I suspect it is with Hotmail. Hotmail dont even know how their system works and the general response from others experiencing the same problm is that they cannot do anything to stop it.
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Commented:
Thanks to both of you!

grblades, I have sent the test e-mail.

jasonsbytes, I'm going to take a look at the stuff you recommended and I will post with my results in a bit.
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Commented:
The only thing our spam checker identified was that you send the email with the from field as an email address only and din't have a name there aswell. This is very minor. You got a score of 0.5 and you need 10 times more than that to get blocked by our spam filter.

Apart from receipent specific measures the only thing you can do to reduce the likelyhood of being classed as spam is to use one or more of the different methods of sender verification :-

SPF - http://www.openspf.org/
DKIM - http://www.dkim.org/
HABEAS - http://www.habeas.com/

Hotmail may use one or more of the above 3 systems when deciding if your mail is spam.

Commented:
Do the emails get blocked at hotmail from a particular domain ? of this guy's band? or from all the domains you have on your server?

Also try to run a check if your server mail server is in any Spam Black Lists, you can do that using the tool here: http://www.dnsstuff.com/ just go to IP Tools -> Spam Database Lookup and enter the ip of your mail server to begin lookup.

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