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If Windows is recognizing your PRS505, you can bypass Calibre and just open an Explorer window to look at the contents of the device, and copy them over to your hard drive. You can then try various hard-reboot methods without risking the contents, and re-import them later.
If there are DRM'd ebooks, there's a chance you'll lose access to them. After you copy them onto your hard drive, check if any are LRX ebooks. Also, you'll lose the bookmarks & page settings.
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