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trouble sending email to hotmail - receiving a 550 response

Posted on 2010-09-21
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Last Modified: 2012-05-10
One of our clients is having trouble sending email to hotmail addresses.

We are running sbs 2003 and using Exchange 2003 for sending email.

We have occasionally had a few issues with being blacklisted - but at present we are not on any blacklists.

HOWEVER, we are still being blocked by Hotmail - when sending mail to hotmail addresses we get the following error:
550 Requested action not taken: mailbox unavailable

I have tried several hotmail addresses, same problem.

I have also used telnet to communicate with Hotmails Mail servers - it allows the connection, but when trying to enter a recipient address, it produces the same error.

Anyway, I emailed Hotmail, and got a response to confirm that our IP has a poor reputation. They have advised me that we need to join their senderID program, I looked in to this and read up on SPF records - as I understand, these records inform mail servers who has the authority to send mail from our domains.

The problem is, I cannot set up an SPF record as our domains are actually hosted with 1and1 - and they apparently dont allow for this.

My question is, is this imperative in order to send to hotmail addresses, or is there another way to repair our reputation - has anyone else had a similar issue and how did they solve it?

I think my options are either move domain hosting/dns hosting to another provider, or perhaps send mail out through our ISP via smart host - is this a common method? Does it have downfalls? And how exactly is it done?

Thanks!!
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Question by:davids355
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p_nuts earned 500 total points
ID: 33726950
If I were you I would move my DNS as soon as possible..

the SPF records should be created.. that's the best way.

Try to convince the hotmail staff to unlist you and they will need proof that you've solved any problems you've had in the past.

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Author Comment

by:davids355
ID: 33727076
What about sending via our ISP, is that a bad idea?
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Expert Comment

by:p_nuts
ID: 33729285
not in general but doesnt really solve the problem in the long run. still no reverse lookup. and if your server is spamming it will just relay and get blacklisted
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Author Comment

by:davids355
ID: 33729799
Yea I don't really want to forward through ISP. Real pain though. Hotmail I must say have been helpfull - much quicker response time than aol. But they say they won't remove us from blacklist until we get the SPF record set up - so I guess the only choice is moving to an external dns provider.
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Author Comment

by:davids355
ID: 33733665
I have been communicating with hotmail, and now, it seems that I can send mail to hotmail addresses again - although they are going into the spam folder...

I am going to open a new question on setting up SPF, will post link to it here...

Thanks for the help so far.
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Author Comment

by:davids355
ID: 33733699
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Author Closing Comment

by:davids355
ID: 33735961
Thanks
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