Exchange 2010 Second domain /alias fails to deliver to some users

I have my primary domain which is assigned as the email address policy in Exchange 2010. I also have two other domains which are two other Nonprofits that we run / do work for. I have never had an issue unchecking the auto apply policy box and assigning a different SMTP address to a user.

Now we have people working across companies and they need to receive email for both address. Ie. Tim@domain1.org (would be the primary) Tim@domain2.org (would be an alias email address). Both would end up in the primary email box.  

I have been able to send emails to those domains with no problems externally/internally to a couple of users. However, when we began using it on a wider scale some of the addresses started to fail.

At first I thought it was McAfee SAAS but after looking at the exchange server the emails are hitting the server and failing to deliver.

Exchange 2010 14.2.247.5
Windows Server 2008R2

I have attached the file with what I am seeing.

Can anyone give me some pointers?

Thanks!
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TimMurpAsked:
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Nick RhodeIT DirectorCommented:
and you verified that on those specific users affected that the email address is in there from the policy?  In the policys are they both set to default or just the primary one?
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Vijaya Babu SekarAssociate Ops ManagerCommented:
First thing, if it was happened for some of user, could you please check the properties of mailbox in email tab. whether it is checked "automatice apply email address policy" or not

Second thing, you can find particular user's OU, make sure the email address policy applied in certain OUs

Thanks.
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TimMurpAuthor Commented:
Thanks for all the advice guys! The user had a different alias pulled when upgrading from 2007 Exchange. We switch from first name to first initial last name. When sending to both her and another user at the same time the email failed. However, when just sending to the second user the email arrived. I altered the first users name and sent again and both were able to arrive. So it looks like everything is working now. Still confused as to why the email failed to two users originally but after fixing the one users profile all emails seem to flow.

Because both answers were helpful, I will award 50/50. For any users coming after the fact. I believe there was some issue with 2007 and 2010 migration applying the new policy to those objects. I uncheck the auto apply policy box edited the smtp and then reapplied to get these users working. Why the email failed to deliver to the two users originally is still a mystery. One which I don't have time to vet fully.
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