Question

Web Server can't send email to hotmail.com addresses

Asked by: PeteJH

Hi all,

We host email internally on an Microsoft Exchange Server.  We also have a web server (at an external hosting company) that uses its own SMTP engine to send emails to website visitors (using our domain name in the from address). This has been working fine, however now we are getting bounced emails whenever the web server sends email to Hotmail accounts. The error message is as follows:

----
host mx2.hotmail.com [65.54.244.168]: 550 Your e-mail was rejected
for policy reasons on this gateway. Reasons for rejection may be related
to content such as obscene language, graphics, or spam-like
characteristics (or) other reputation problems. For sender
troubleshooting information, please go to http://postmaster.msn.com.
Please note: if you are an end-user please contact your E-mail/Internet Service
Provider for assistance.
----

I have done a bit of research, and apparently other people have been having this issue and it is due to Hotmails new filtering system. I assume it does a check to make sure the sending mail server is legitemate. I have suggested that the website relay the email through our in-house email server, but this will not be easy to achieve without re-coding parts of the website (I am not responsible for that).

I would appreciate any ideas or suggestions that anyone could give me regarding this matter.

Thanks

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Asked On
2007-07-09 at 19:07:37ID22684938
Tags

hotmail

,

send

,

email

,

server

Topics

Web Servers

,

Email Servers

Participating Experts
1
Points
500
Comments
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Answers

 

by: ahoffmannPosted on 2007-07-09 at 23:38:18ID: 19451065

> We also have a web server (at an external hosting company) ... to send emails to website visitors (using our domain name in the from address).

are you saying that the mail server is for example my.foreign.mail.tld while your comapanies domain is my.own-domain.tld and the mail server sends emails with a From: user@my.own-domain.tld

Then it's no wonder that a reliable mail server rejects such mails, 'cause sender and claimed sender (in From:) are different which is a common spam method.

 

by: PeteJHPosted on 2007-07-10 at 00:24:51ID: 19451213

Thanks for the response. I'm not sure I understand what you are saying, but I will try to explain the situation again:

- We have an external host that runs DNS only for ourdomain.com.
- The MX record (and mail.ourdomain.com) points to our in-house mail server.
- The www.domainname.com record is pointing to our web host's server (which is in another country). This web host is not the same company that runs the DNS on our domain.

The external web server is sending email (using its own SMTP server) to be from myaddress@domainname.com. This email sends perfectly to all email servers except the Hotmail Servers. I suggest this is becuase they are doing some sort of check at the DNS level or something.

This is why I am looking at getting the web server to relay the email trough our internal server. Does this sound like the best option?  

 

by: ahoffmannPosted on 2007-07-10 at 02:18:38ID: 19451714

internal vs. external and same vs. other country does not matter in a virtual world. Also the MX record for your incoming mail server does not matter.
What matters is the IP and its mapping to a FQDN of your sending mail server as done in DNS entry seen in public.
So if the IP of your mail server resolves to a different domain than your website (which is used as sending domain in the mail's From: header), then there is a mismatch which most mail servers will reject.

 

by: PeteJHPosted on 2007-07-10 at 16:53:25ID: 19458797

I understand what you are saying, but it only seems to be Hotmail's mail servers that have a problem with it. They send out to hundreds of other emails addresses without issue.

How do you get around the issue in your environment?

 

by: ahoffmannPosted on 2007-07-10 at 23:43:02ID: 19460252

> .. but it only seems to be Hotmail's mail servers ..
well, then their server is propper protected and cannot be used as open relay, that should be the case for most servers.

As I said: it's bad practise to send mails with faked headers, reliable servers should reject it. You have to set up a server with a proper DNS entry, or find a open SMTP relay.

 

by: PeteJHPosted on 2007-07-11 at 00:02:17ID: 19460315

Thanks for the advice.

20120131-EE-VQP-002

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