outbound smtp cant send to hotmail.com

KellyKeeton
KellyKeeton used Ask the Experts™
on
I have a issue with my Exchange 2003 server and outbound smtp.

I can send email to all domains i have tried except hotmail.com

http://www.dnsreport.com gives me no errors or warnings other then the lack of a SPF record.

I can telnet to mx1.hot... and manually submit a email to the queue with no errors back from telnet. SO i am not blacklistes or blocked.

I think the email is going into hotmail but it will never deliver. I can send email from yahoo to hotmail and its instant. but from my domain to hotmail it will not deliver. also no error.

my smtp log will show something like this
64.4.50.99 ehlo -0
64.4.50.99 - - 0
64.4.50.99 mail -0
64.4.50.99 - - 0
64.4.50.99 RCPT -0
64.4.50.99 - - 0
64.4.50.99 BDAT - 0
64.4.50.99 - - 0
64.4.50.99 QUIT

i have searched only to find that it might be related to a reverse lookup, my reverse lookup is returning to the ISP provider namespace and not my namespace the email is from.

Wondering if its hotmail issue or my issue and how to fix if so.
64.4.50.99 RCPT
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Author

Commented:
update and point update

from my asp.net application (dasblog) i can send out a relay email. however from OWA and telnet and Outlook i still get the same error from hotmail.

Why is the issue only effecting "legitimate" email sources and allowing the stupid relay from the asp.net?

Commented:
well i am not sure i can help but why dont u creat an smtp connector and use ur isp's mailserver  as smrt host for relaying ur mail...in the smtp connector for the domain that is allowed to  use the connector (address space section)make sure hotmail.com is added....try this and see if ur problem is solves.....
asp.net uses port 25 on ur server(not ur exchange servers smtp server) and most likely is relayed through ur isp's mail server...sorry just guessing not familiar with that application....


Commented:
There are a number of issues around "problem domains"

Try this

http://www.amset.info/exchange/smtp-connector.asp

Hope it helps.

Mark
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Author

Commented:
you dont have to be familear with the app. as far as i know all asp.net works the same for relay. However thats just a "loophole" in the problem the application is not using my ISP mailserver and neither do I. I dont want to rely on them or use the service they provide. Thanks a lot for the suggestion but just not what i am looking for.

THe asp application aside my issue is that exchange is not sending emails  
OWA/Exchange -> Exchange2003 -> hotmail

exchange is sending emails
OWA/Exchange/Relay - > Exchange2003 -> domain.com
asp.net Relay - > Exchange2003 -> hotmail.com

using someone elses smtp is not a option i choose to use (thanks for the tip however)

Hotmail is taking recipt of the email it just wont deliver it to the mailbox

Author

Commented:
@marklar1

hrm this looks to be going a way i dont want it to - can i get a explination on why my relay will send email correctly and the same smtp connector wont allow email from OWA

Commented:
well then create a connector and send directly mail to hot mail.com.....in the smart host section put the ip address of hotmail mail server...and see if that would help u....
a lot of folks have ur kinda problem....sometimes connectors help...and sometimes it is the AV or anti spam software the culprit.....
You stated:
"i have searched only to find that it might be related to a reverse lookup, my reverse lookup is returning to the ISP provider namespace and not my namespace the email is from."

Have your ISP create a reverse DNS record that points to your external IP address.

If you have a dynamic IP address, they will not be able to do this though and the only other option is to relay messages to problem domains through your ISP's SMTP server.

Author

Commented:
problem unsolved hotmail support didnt help either, i set up a second SMTP and just relay the email to hotmail thru that server, from the same IP even. but it works.

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