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Outlook 2007 ost file not Syncing with Exchange 2010

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I have  a user that has a 7GB mailbox and is using cache mode on outlook 2007.  They have had lots of problems with their email contently being reindexed and for no apparent reason.  Recently we have found out that their ost file has not been syncing with exchange when we changed them to online mode instead of cache mode.  So they are back into cache mode because their email works just slow and has to re index at random.

I have found that they have been gettign sync errors saying that their is a problem with their ost file and that we should run scanpst.exe.

I have ran scanpst several times and every time it says that it has detected issues and then I say ok to repairing them.  It finishes and then when back in outlook they continue to get the sync errors stating that scanpst is needed.  

I have also ran scanost.exe and this fails in about 30 seconds with the following:

18:09:10 Terminated in error

18:09:10                                [80040600-20070903-0-310]

18:09:10                                Errors have been detected in the file C:\Documents and Settings\user\Local Settings\Application Data\Microsoft\Outlook\outlook.ost. Quit Outlook and all mail-enabled applications, and then use the Inbox repair tool (Scanpst.exe) to diagnose and repair errors in the file. For more information about the Inbox repair tool, see Help.

18:09:10                                Microsoft Office Outlook Offline Folders

18:09:10                                For more information on this failure, click the URL below:

18:09:10                                http://www.microsoft.com/support/prodredirect/outlook2000_us.asp?err=80040600-20070903-0-310

Since the user has spent months organizing his email and exchange doesn't have his email like that it just has everything in the inbox I want to do the following:
- output his email (outlook running in cache mode) to a pst file
- switch outlook to online mode
- Delete most of his email (will have to leave few emails that are in the inbox that have not been included in the pst file)
- import the pst file so that Exchange will now have the email organized the way the user wants it

My question is: Is there a better way to do this?  I'm sure this is going to take days to do and with the 4 day weekend coming up this would be the best time to do this.  


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