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I don't have a T-1, but the file system works anything like the 350, you can do it easily with Calibre. I make my own covers for my PDFs and just stick the cover.jpg file in the appropriate directory for the PDF on the reader and in my Calibre Library.
If the basic T-1 directory structure has a folder for each book, or a specific name for the covers for each book, you could probably do it without using Calibre using the same method. I just make my images 800x600 and make them B&W and compress them to smallest file size without losing quality.
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