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The permission denied is almost certainly because there are too many files/directories in the root of the Kindle drive and it is formatted with FAT16 instead of FAT32.
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Checked this, the Kindle is already formated FAT32. Besides, I really don't want to jailbreak the Kindle if at all possible.
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Try running whatever disk checking tool you have with OS X and see if you can find what the problem is witht he Kindle filesystem. Also, try checking the permissions
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Tried all this. Couldn't find any problems. However, I also can't seem to duplicate the errors anymore, so something clearly changed. If the problem recurs I'll keep the last suggestion in mind and try that then. Doesn't seem to be much point otherwise.