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Outlook Nickname-Cache after new AD Domain

I have had to deal with this issue for a few smaller networks, but I now have to find a way to automate this issue as I am not about to do the same for 100 Users :)

We are setting up a new AD Domain, and manually migrating User Profiles, setting up new Exchange Mailboxes and importing in from Exmerged PST.
Outlook 2010 and Exchange 2010 is being used, and data is coming from Outlook 2003 and Exchange 2003. We will also be migrating Nickname-Cache into Outlook 2010.
Issue is that when a User goes to send to an internal User from their NK2 (Suggested Contacts) in Outlook they will receive a NDR as I believe the entry will be looking for old distinguished domain name or email address.
Is there a way I can ensure this does not occur? Like editing new AD User accounts to include legacy user accounts?
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Flipp
Asked:
Flipp
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2 Solutions
 
agonza07Commented:
Use NK2Viewer and delete all entries that have the old domain name.

http://www.nirsoft.net/utils/outlook_nk2_autocomplete.html
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agonza07Commented:
Also make sure to delete the X400 entries. Those can be a pain too.
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FlippAuthor Commented:
But that means editing everyone's NK2 file? I can't afford to spend time doing that for every User.
Surely there is a way to use ADSI Edit and add legacy distinguished name in?
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agonza07Commented:
Its got a command line so you can just set up a batch program or something. Just put it out as a GPO.

You can go ahead and edit everyone's account to include the old domain, but you are also going to have to add the X400 stuff too.

Here's a script to add an SMTP address to every account.
http://www.activedir.org/Articles/tabid/54/articleType/ArticleView/articleId/32/Default.aspx
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Simon Butler (Sembee)ConsultantCommented:
The problem with the nicknames files is going to be the old aliases. This article from the SBS team explains the problem and a solution quite clearly:

http://blogs.technet.com/sbs/archive/2009/05/21/cannot-reply-to-old-emails-or-modify-old-calendar-items-after-pst-mail-migration.aspx

Simon.
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agonza07Commented:
I guess I meant X500 instead of X400.

They are a pain to deal with, but Sembee2 is correct and Flipp your initial thought is also correct in that if you edit just the NK2 file then when people reply to old email it will not go through due to the X500 address.

It's best to either script it or use ADModify to bulk edit your users and add the old SMTP address, and the old X500 address.
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FlippAuthor Commented:
Awesome feedback all .... I went ahead with a script with nk2edit which has saved me a lot of time. I think admodify would be best to use next time round though.
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agonza07Commented:
Just be careful with old emails and if people reply to them. They will not go through and come back as NDRs because they will have X500 references that came from you Exchange 2003 setup.
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FlippAuthor Commented:
Ah yes of course ...... can you give me some more information around what is required with ADMod to update new AD Users?
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agonza07Commented:
Exactly what Sembee2's link shows.
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