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Exchange 2010 to 2003 Mail Flow Issue

I'm currently having an issue where our exchange 2010 server is no longer sending emails to our Ex03 users. We currently changed the primary domain for email accounts on both Ex2010 & Ex2003 environments. When I send an email to a test account in my Ex2003 environment from a Ex2010 user account I get the following error from my delivery report tool:

"Pending
3/12/2015 11:59 AM Ex2010.domain.net
The e-mail address for recipient "test@test.com" was updated to the e-mail address "test@testnew.com". The message is in the process of being delivered."

"The last attempt to send the message was at 3/12/2015 12:12:10 PM (UTC-05:00) Eastern Time (US & Canada) and generated the error '451 4.4.0 Primary target IP address responded with: "535 5.7.3 Authentication unsuccessful.." Attempted failover to alternate host, but that did not succeed. Either there are no alternate hosts, or delivery failed to all alternate hosts.'."
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AmitIT Architect
Distinguished Expert 2017

Commented:
You need to enable anonymous setting on 2003. Check this.

https://kb.acronis.com/content/35445
Bill BensonPrincipal Consultant

Commented:
Does mail flow from 2003 to 2010? Do you have an RGC (routing group connector) from 2010 to 2003?
Will SzymkowskiSenior Solution Architect
Most Valuable Expert 2015
Top Expert 2015

Commented:
primary domain for email accounts on both Ex2010 & Ex2003 environments. When I send an email to a test
Did you create a new Accepted Domain for this new SMTP domain? Also, did you create Email Address Policies for this new Accepted Domain and apply them to your users?

If you send an email from E2010 to another user with a E2010 mailbox does this work?

Also, try adding the Authenticated Users back to the SMTP Users Tab.

Will.
Martin EhrhardIT Director

Author

Commented:
I do have an RGC setup between 2010 & 2003, this coexistence has been setup for a few months now without any issues. I feel as if there may be some weird issue with AD and authentication itself since I coincidentally ran into domain authentication issues with a SQL server.

The new domain is setup as an accepted domain and as the default. I did not create an email address policy for this added domain. But, emailing users within the Ex2010 environment works fine.

Will,
Are you referring to the receive connectors for modifying the authenticated users?
Will SzymkowskiSenior Solution Architect
Most Valuable Expert 2015
Top Expert 2015

Commented:
Are you referring to the receive connectors for modifying the authenticated users?
Yes have you changed anything on the default receive connectors for Exchange 2010?

I did not create an email address policy for this added domain.
How do users get the email address if you did not create a policy to apply on the mailboxes?

Will.
Martin EhrhardIT Director

Author

Commented:
No change made to the default receive connectors for Ex2010. Once I added the domain to default policy in Ex2003 system manager the domain was available to all users including my Ex2010 users.
Will SzymkowskiSenior Solution Architect
Most Valuable Expert 2015
Top Expert 2015

Commented:
Based on the error message it is clear that this is an authentication / permissions issue. Take a look at the below KB for additonal steps for Troubleshooting mail relay for Exchange 2003.

Search for 5.7.3 in the link below...
http://support.microsoft.com/kb/895853

Will.
IT Director
Commented:
Hello all,

Thanks for the suggestions. As it turned out the problem was due to a bad MS update (KB3002657) released on the 11th of this month (MS has acknowledged this update to have a bug). I removed this update on our domain & exchange servers. After uninstall everything went back to normal.
AmitIT Architect
Distinguished Expert 2017

Commented:
Thanks for the update.
Martin EhrhardIT Director

Author

Commented:
MS support for directory services provided the fix to this problem.