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Outlook just sucks in general. What's most laughable is it's incredibly piss-poor search capabilities.

Try Lotus Notes. Outlook is a shining unicorn in comparison. Urgh.

I agree with this, but I will say that Outlook 2010's search is a vast improvement over the previous versions.

Agreed, they are improving, but frankly they didn't have much of anywhere to go but up.

I find Xobni helps a lot to find lost stuff in Outlook, although the latest update to Xobni seems to have made it a bit of a CPU pig. :-(