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I just signed up for a new Outlook.com account and synced my existing Gmail account with my Windows Live account. However, when I view my Gmail messages within Outlook.com the only messages that show up are from 2009 and prior.

How do I get all my messages to show up?

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I would try setting this first option, and then resyncing. Pop Download settings
I'm thinking you might have checked the second option in 2009.

  • Oops, I read prior as after. – Louis Aug 1 '12 at 4:28

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