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google fu failed me, need gmail help by Dad2TZK2009-04-10 14:50:56
  IIRC, Gmail only allows you to... by SnappingTurtle 2009-04-10 15:01:43
... download an email once. That would explain why you can't download old emails.

If it turns out that is the problem, perhaps there's something on Gmail's help site about how to deal with it. Alternatively, perhaps they would make a special exception for you and reset the "downloaded" flags for you. As was mentioned in another post, be sure Outlook doesn't delete emails from the server after downloading them.
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