Link to home
Start Free TrialLog in
Avatar of KThrace
KThrace

asked on

Exchange 2003 - Office 365. Still using Exchange 2003 for relay

Previously used Exchange 2003. Installed Exchange 2010, moved mailboxes to 2010 and then migrated to Office 365. Redirected MX records, Purged mailboxes on Exchange 2010. Everything is working fine with one exception.

Devices/Software were still using Exchange 2003 to relay e-mail. I set up a new SMTP server and moved everything to use this. However, I still have one web service that is using Exchange 2003 to relay e-mail - I'm not a developer, I can't modify the code. I'm waiting on the developer to modify the code. In the meantime, messages that are sent from the web service, via Exchange 2003 to previously internal e-mail addresses are failing.

Error logs are pointing to an NDR being created:

A non-delivery report with a status code of 5.4.6 was generated for recipient rfc822;user@domain.com (Message-ID  <2079311841.1492.1433304180817.JavaMail.tzweb@ACTZW02>).  
Cause: A forward loop was detected by the categorizer. This is a common hosting configuration problem caused when someone uses the provisioning tool to create a contact in one organization unit and creates a user in a different organization user that share the same e-mail address.    
Solution: Verify that you do not have a user in organizational unit and a contact in a different organizational unit that have the same e-mail address.

https://support.microsoft.com/en-us/kb/324732

The KB says I should clear "This exchange organization is responsible for all mail delivery to this address" box. But, unfortunately, I can't do that because it's the Primary SMTP address.

Any suggestions on how to fix this?
Avatar of KThrace
KThrace

ASKER

I should add that I also made all users Mail Enabled with the correct ProxyAddresses. Using Directory Sync, so I can manage the users e-mail addresses etc from Active Directory which will then sync to O365.
Avatar of Delphineous Silverwing
Have you tried configuring the Exchange 2003 SMTP connection to use a smart host, pointing to the O365 SMTP gateway?
Avatar of KThrace

ASKER

I tried setting the SMTP Connection to use the real SMTP server as a smart host, but it didn't work - I'm assuming because Exchange 2003 still thinks it's responsible for e-mails delivered to this domain and so it ignores the SMTP relay...
ASKER CERTIFIED SOLUTION
Avatar of Delphineous Silverwing
Delphineous Silverwing
Flag of United States of America image

Link to home
membership
This solution is only available to members.
To access this solution, you must be a member of Experts Exchange.
Start Free Trial
Avatar of KThrace

ASKER

Yes, all mailboxes are in the cloud and have been disconnected.. All users have been set to mail enabled users.

I JUST now in the recipient policies added a new primary SMTP address that is different from the current domain and set it to primary. I unchecked "This exchange Organization is responsible for all mail delivery to this address" and then unchecked the SMTP policy. I then disabled the recipient update services. I did a test and it seems to work. I'm just concerned that in a few hours something is going to break...
<fingers crossed>
Avatar of KThrace

ASKER

So far so good...
Avatar of KThrace

ASKER

Looks like we're good! Thanks!