Exchange 2010 and Outlook 2010 not cooperating

I deleted a user on AD and recreated it, then recreated the mailbox.  internal users CAN"T email the user because they get UNdeliverable bounce backs.

the're all using cache mode and iether on outlook 2007 or 2010.  the only way to fix it is by disabling cache mode, sending the email a test email, and then re-enabling cache mode.

what is a good way to fix this autmoatically. i've already tried updating the gal on EMC and downloading the address book via outlook.
Anthony H.Asked:
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Rajitha ChimmaniCommented:
Your X500 will be something like the below:

/o=South/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=Tpro

Add this to the mailbox properties as custom email address as mentioned in my last comment
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suriyaehnopCommented:
This is due to cache issue, to resolve it let you user to manually download the new copy of address book to the Outlook. Once you have download it, let about 48 hours for Outlook in cache mode take effect.

How to download Address Book http://emds.unt.edu/node/344
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traoherCommented:
If you use GPO, you can turn cache off for a while then turn it back on so you don't have to touch every workstation.  you will need custom ADMX file for the version of outlook you are using though.

Turn off/Turn on cache mode has side effects well, deleted emails may show up, read emails may be unread again, confusing users more.
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Rajitha ChimmaniCommented:
You must also add the legacy email address of the old mailbox as X500 address in the newly created mailbox.

The senders will continue to have problems sending emails when they select the user from their autocomplete cache.

You can determine the X500 address to be added by checking one of the delivery failure messages received by the senders
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Anthony H.Author Commented:
Actually i deleted  the offline address book items under %appdata% folders and that reset it. Is that ok?
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Rajitha ChimmaniCommented:
That will download the offline address book. But if the senders select the name from OUtlook autocomplete cache (stored in .NK2 file) then they will receive delivery failure. That is the reason why you have to add X500 address.

However, if they select the name directly from address book it would be fine.
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Anthony H.Author Commented:
What is the x500 address?  Not familiar with that. How/where do i add it?
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Rajitha ChimmaniCommented:
You can add it from a mailbox properties Exchange Management Console.

Under Mailbox Properties->EMail Addresses tab - Click on Add->Custom Address - Give the address type as X500.

A sample X500 address looks like:

/o=domainl/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=Usernameoralias

If you provide the delivery failure i can give the exact X500 address.
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Anthony H.Author Commented:
Generating server: EXCHANGE.south.local

IMCEAEX-_O=SOUTH_OU=EXCHANGE+20ADMINISTRATIVE+20GROUP+20+28FYDIBOHF23SPDLT+29_CN=RECIPIENTS_CN=Tpro@south.com
#550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ##
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Simon Butler (Sembee)ConsultantCommented:
Once again, everyone is going on about the OAB, but has failed to mention that you need to force an update of the OAB before updated information can be downloaded.

get-offlineaddressbook | update-offlineaddressbook

Wait half an hour and then force a download.

However anyone replying to messages sent from the old account isn't going to work correctly, unless you add the X.500 address in, and you also need to be aware of the nicknames file.

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

And this tool will create the address from an NDR for you:
http://poshcode.org/3516

Simon.
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