Tons of issues moving Outlook accounts

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Outlook version
Outlook 2010 64 bit
Email Account
I will try to explain this the best I can, it's a bit confusing for me.

My boss has an old Win Xp machine. It has Outlook 2003, with his primary email account he uses currently. It also has an address book with it. He also has Outlook Express on the XP machine, and within in it is his data from an old pst file with 1000's of emails from 2005 and before.

So now he has a new Win 7 PC with Outlook 2010 on it. I have successfully loaded up his primary email account from Outlook 2003. But.. It didn't carry over his contacts. Also, his email inbox only goes back a couple weeks.

I can't explain all the methods I've tried to get both his old OE and Outlook 2003 info over. It would take forever, and to be honest, I don't remember all of what we tried. But I can tell you what we need to transfer and how he wants it.

I have all of his Outlook 2003 contacts on 2010 now. But, the categories didn't carry over. All 5000 (yes, 5000!) carried over in to one Contacts folder. We need to have the categories carry over. Not only from Outlook 2003, but from OE. The categories carry over to Windows Live Mail. But when exported from there, and loaded into 2010, the categories don't carry over.

We need his full inbox on 2010 from his primary email. Not just his inbox going back a couple weeks.

We need his old OE emails to be on 2010. I have gotten all the folders with his emails from OE to import in to 2010. But for some reason, each folder only has a maximum of 5 emails in it. He has 1000's in some of these folders, and he wants them on 2010.

Please let me know if I need to clarify anything. I can even get some screenshots if needed when he's away from his desk.

Did you run upgrade to color categories? It's on the right click - Properties menu of the root level folder where Outlook today comes up when you click it.


How did you move the mail from OE to Outlook 2010?
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