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When you connect the Kindle to your PC and look in the linkss/screensaver folder, have your pictures all been renamed to have numbers at the beginning of their names? That's the telltale sign that the random feature is working.
Basically, upon every reboot, the files get reordered by changing those numbers that have been appended to the filename. That's what creates the random display order. It's not really random since pics show once in sequence until the end of the list is reached, then the exact same cycle is repeated. When you tire of that order, reboot the Kindle, and they'll be shuffled again.
-HM
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