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WiFi or 3g?
When it isnt working correctly look to see if you are on 3g or Wifi ...
I have found that for some reason the WiFi @ my office is flaky. Usually I get the email on my droid before it shows in my Outlook client on my lap top. When I don't hear DROID! and email is poping into my inbox in outlook, if I disable WiFi it gets the push from the server over 3g. Re-enabling WiFi re-associates it with the wireless network and it gets the 'pushes' over the net.