Send As works on OWA, but not Outlook

I have created a mailbox that needs to have people be able to "Send As" that email address.  This is working from OWA, but it won't work with Outlook.

I'm using Outlook 2007 with Exchange 2010.

I have tried adding them to the "Send on behalf" list from the EMC, and have tried adding them to the "Send As" list from the EMC as well.  Both methods give the same result.

In my research, I discovered that OAB files might need to be updated so I downloaded the Address book from Outlook and even deleted the OAB files from the profile.  Nothing has worked.  I have also tried running Outlook with Cache mode dice.

The fact that it works from OWA and not Outlook tells me that something is up with Outlook.

This is crazy and I just can't figure out why it's not working.
Darryl AllenAsked:
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Adam FarageSr. Enterprise ArchitectCommented:
It doesnt work for all users, or some?

I would think your OAB might not be generating properly. During *off hours* try forcing OAB regeneration and look in the Event Viewer: Application logs to see if there are any related errors.

I would also look at AD replication, as this could be a specific issue also.
Vijaya Babu SekarAssociate Ops ManagerCommented:
Better you can reconfigure the outlook profile. because it will create new ost file and will happen OAB syschronization. or you may follow the below steps

It might be problem with local outlook cache issue. so you would need to update your OAB through powershell or EMC, Please run the below cmdlets in Powershell

Get-offlineaddressbook | Update-offlineaddressbook


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Darryl AllenAuthor Commented:
First, is PowerShell the only way to invoke those actions?  Second, I'm assuming you are talking about running those commands on the Exchange server?

I was able to do a "Send As" from my Outlook this morning, so obviously something changed over night.  However, I still have another user that this is still happening to.  As far as I can tell, I haven't set him up any different than myself.  OWA works for him, just not Outlook.
Darryl AllenAuthor Commented:
In the end what cleared this up was the OAB processing that takes place once a day.  That's crazy to me, but I guess Microsoft has their reasons for not make changes available within a reasonable amount of time.
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