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Just had a friend update to Leopard (he's on a new Mac Pro). However, when we ichat, both the "Share My Screen..." and "Ask to Share..." options for Screen share are grayed out, on both of our Macs (i.e., he can't do it, and neither can I).
He's def running 10.5, his iChat version is 4.0.
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Are you both on broadband?
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We are. Very fast connections. And all other features if iChat (video, audio) work fine.
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iChat has a feature called the "Connection Doctor" available in one of the menus.
Run it and see what capabilities it says you each have.