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Originally Posted by Don't Panic!
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Not good news I'm afraid.  I downloaded Rudolph the Red-Nose Reindeer in Portrait Mode and it displayed as a one inch square until I toggled WMP10 for PPC to landscape. Then it displayed as what I was used to as a Portrait mode sized flick on older WM Players for Pocket PC. BTW-This Rudolph is an 8-minute cartoon not the Television version with Burl Ives as the voice of the snowman. :)
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Bobby there is a setting in WMP10 to Shrink to fit window (see image ) ,check that and it will stretch or shrink your video to fit in the window but uncheck it and your video will play the size the video is encoded to. Your example of Rudolph is not a true portrait size video it has been encoded at a resolution of 208x160 I have included some images to show Portrait size in WMP 10 incuding the Rudolph one with the shrink to fit window unchecked.