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Outlook 2010 instant search breaks intermittently

I've run into an issue in my environment that is having me scratching my head.

Instant search will not work, though only intermittently. Searching for a common string returns results, then later in the day it will return nothing for long periods of time, or only return results for a set range (most recently I attempted to search for my boss's name, and it only returned results going back to the beginning of last month and no farther).

Exchange 2010

Windows 7 64-bit

Outlook 2010 64-bit and 32-bit.

I have rebuilt the index, change the index location, turned off the indexing service restarted and turned it back on, I've double-checked the location of the OST location, cached exchange mode is turned on, confirmed proper permissions to all files involved. The issue occurs on users who have been here a long time as well as new users with freshly imaged computers. I've rebuilt Office installation, as well as windows. I've created a new Outlook profile. The only commonality I've been able to pinpoint is that the users who have this happening have two email addresses (user@contoso.com and user@secondcontoso.com, for example).

Any ideas? I am at my wits end. 


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