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When I'm working on multiple monitors/desktops and I switch to one and want to do some work there, but my 'active window' context is in previous spot where I was working!

I wish someone would invent some type of eye tracking that would intelligently assign the context to open windows on your screen(s).

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You could use a window manager that supports following (instead of clicking) the mouse or keyboard shortcuts to switch focus. Maybe I have been on the geek-road too long, but the latter should be supported in Windows/OS X as well, shouldn't it?

In OS X could it be as easy as whatever monitor the dock you are using makes the app appear on that screen? I think that would be a better fit for me.

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