Unable to send mail to some domains

Smart host configuration?

I have had this similar issue where I was not able to send emails to hotmail
What we tried adding smart host for our ISP and it didnt work
It coming back with message saying it rejected the email
So in order to test we tried sending through our servers and it went OK
Luckily We had to change ISP after couple of weeks and with new ISP everything went smoothly

Hope this information helps

Regards
Munish

dexIT:  Not very many options to set on the postini side of things.  It is configured to accepted SMTP from our server's ip (12.229.68.25) which is also the reinjection server.  It is also configured for smtp only (no tls settings).  Is this what you meant?

Please have a read through my article about problems sending mail to one or more domains, check
you are not blacklisted, not badly configured and if you are, rectify the situation and your mail
should flow:

https://www.experts-exchange.com/articles/Software/Server_Software/Email_Servers/Problems-sending-mail-to-one-or-more-external-domains.html

alanhardisty:
Great article - I bookmarked it for future reference.  It appears, however, that I have everything configured correctly.  The part that I am not sure of relates to the ptr records.  We use postini for filtering inbound mail so we fall into the category of having separate inbound/outbound ip's.  The ptr for my server address (12.229.68.25) does exist and points to mail.eastbrookhomes.com.  The mx record can be seen in my original post and points to the postini servers.

What about the FQDN?  On the exchange box the FQDN is set to the the specific server name on our network (ebmail1.eastbrooknt.eastbrookhomes.com).  Is this correct?  Please see attached image.

Thank you for your help.

outbound.JPG

It sounds like you need to change the FQDN of your mail server to mail.yourdomain.com from ebmail1.eastbrooknt.domain.com.

Change that and try sending to the problem domains.

What do you make of this?

This is the response I received back from Microsoft Hotmail support:

Hello Tim,
Thank you for writing to Windows Live Hotmail Domain Support. My name is Imee and I will be assisting you today.
Messages from your IP (12.229.68.25) are being filtered based on the recommendations of the SmartScreen filter. This is the spam filtering technology developed and operated by Microsoft.
Enrolling your IP address to our Junk Mail Reporting Program (JMRP) should help avoid common deliverability issues. This program is in place to help legitimate companies deliver their email messages to Hotmail users.
I would strongly suggest for you to enroll to our JMRP - Enrollment with this free program will benefit you as a sender as it will keep your email lists updated and populated with interested Windows Live Hotmail Customers. This program will help you to remove those Windows Live Hotmail Customers who do not want to receive emails from your company. Please visit http://support.msn.com/eform.aspx?productKey=edfsjmrpp&page=support_home_options_form_byemail&ct=eformts
After you have taken steps to enroll in JMRP, please contact us again so we can assist you further. Please include the SRX number you were given after you complete the enrollment.
For more detailed information about best practices delivering to Live Hotmail, please review the following white paper: http://download.microsoft.com/download/e/3/3/e3397e7c-17a6-497d-9693-78f80be272fb/enhance_deliver.pdf 
I hope that the information that I have provided to you has been helpful. You may also be able to find additional information on common delivery questions at the Hotmail Postmaster Site found at http://postmaster.msn.com/
Sincerely,
Imee
Windows Live Hotmail Domain Support

Hmmmm - do you send out bulk mailings from your server?

We do not, however, I am sure that some of our employees use there own distribution lists for mailings they send.  We use a service (iContact or MailChimp) for subscription-based mail (which are not frequent).

I have since received this message after submitting my spf record to Microsoft to receive a SenderID.  Look at the suggestion about not recommending a ptr.  I thought you were supposed to have a ptr - this seems to go against everything else I have read.  Does anyone have any insight on this?


Thank you all for your help thus far!

Any reason why you contacted Microsoft for SPF?
You can use the tool at:
http://old.openspf.org/wizard.html
That should ask all the right questions and provide you with a suitable SPF record.

I am still struggling with this issue when sending to many different domains.  Microsoft placed me (finally) on their mitigation list and supposedly I am able to send successfully to their domains but this seems to have set off a firestorm of other domains that are problematic.

There are two things that I can see as potential problems.  1) The AHBL is waging war on GoDaddy which is where our website is hosted.  See this article for more info:  http://www.godaddyignoresabuse.com/  there is nothing I can do about this and it is only my web hosted there.  2) My SMTP banners do not match my rdns.  This is because I use postini for spam/virus filtering.  Should this be a problem?  Is there any way I can get around this and still use a third party for filtering?

Alan, I didn't contact Microsoft for spf.  They made recommendations to me during this whole process including submitting my spf to them for approval and inclusion on their mitigation list.  I actually did use the spf wizard to make check my settings.

DOES ANYONE SEE SOMETHING THAT I HAVE MISSED???

Thanks.

Very Random - but glad it is resolved.