Exchange server and outlook 2003

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I just purchased a new PC for my employee and setup his exchange account on the computer to sync up with his account on the server. While syncing I was expecting many e-mails, calendars and contacts to appear in outlook, but none came through; this clearly indicates that whatever he received/added and modified in his outlook was never saved on the exchange server.

Being that he is still using his old PC, is there an option I can select in outlook to sync up all his messages/folders/contacts and so on so that I can sync them on the new PC?

Thank you
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You would have to check the old computer to verify where the messages were kept.  It sounds like data was just kept in a personal folder on the computer.  Items should be able to be moved/copied to the server on a per-folder basis.  Once on the server, they should start showing up on the new system.  There isn't a "one-click" way to move the personal folder data to the server.
Sounds like this user may have outlook set to use a personal folders.  On his old PC, just move / copy/ import everything from the personal folder into the Exchange inbox.  Before doing this, you will want to be sure Outlook is set to deliver to the Exchange Inbox so items don't start popping back into personal folders.
As above, you can use Outlook to import PST data into the mailbox, it's very straightforward. This is the method I would choose in a one-off scenario like this.

But there are also some tools you can use to import the PST data from the server side, if it comes to that. Exchange 2003 supports exmerge, although you should be aware that exmerge has a 2GB PST limit. In Exchange 2007, you use the import-mailbox powershell cmdlet, like this:

In Exchange 2010, you use New-MailboxImportRequest:

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