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Exchange 2013 new user email routing test

Posted on 2014-01-16
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Last Modified: 2014-01-17
Hello All,

I have a hybrid configuration with my on premises Exchange 2007 box and Office 365 (almost all mailboxes migrated to 365).

I have recently added an Exchange 2013 server to my organization with another namespace. This new Exchange box is running in coexistence with the Exchange 2007.

This Exchange 2013 implementation was done because eventually we will be migrating our MX to office 365 and will decommission our Exchange 2007 box after doing so. The Exchange 2013 will remain in our organization hosting a couple of mailboxes (with a different namespace as mentioned) for some LOB applications.

To test email flow I have created a user and mailbox. This mailbox was auto created with a couple of SMTP address (due to exchange policies), one with the old namespace (the one hosted by my exchange 2007 and office 365) and another one with the new Exchange 2013 namespace.

I started to perform mail flow tests by sending and receiving. Everything perfect. Also opened the header of the emails received and verified that the box routing the emails was my new Exchange 2013 server.

Now in order to reassure that everything was getting routed using the new namespace, I deleted the old SMTP address of the user and left the one with the new namespace. I started to send test emails from the new user, worked perfect. Now, when I try to reply to that test email, I am getting an undeliverable message. this message reflects the test user email with the old namespace (the one I deleted) and is reaching my old server, which responds, "Hey I dont know this user". Even if I type it in the email with the new namespace, it will send to the old namespace.

The interesting part is if I send an email from an external email address it delivers to this new user with no problems, which makes me feel that my outlook client is suspicious.

Please enlightened me if possible!
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Question by:LuiLui77
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Will Szymkowski earned 500 total points
ID: 39787537
Did you also remote the old X400 address? This is for routing to legacy servers that are in your environment. If you remove that it will not be able to route back to your Exchange 2007 server.

Also Is this a caching issue on the opposite machine (autocomplete/nickname caching)?

If you open a new email and get the Exchange 2013 user from the GAL does this work for you rather than simply typing the email address in?

What does message tracking tell you when it is undeliverable?

Will.
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Author Comment

by:LuiLui77
ID: 39789057
Hi Will, it was most probably a cached issue that got cleared out by today. I think it was cause by the updated address book not being available yet.

Today I made the test and seems to be working perfectly.

Thank you.
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