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The Sony uses MP3 tags to organize your music or audio book titles into 'albums' and 'tracks' so if your MP3's have the proper ID2/ID3 tags, then all you have to do is drag all the files onto your reader at the same time.
I just put all the MP3 files for an album into one folder, and then drag that folder into my PRS-650's \database\media\audio folder.
If you are using the media player to do the transfer, then this is more properly a question for some 'windows' forum, but you can probably do something like click the first song in the album, then hit the shift key while clicking the last song to select them all at the same time, then transfer them the same way you now do for a single song (just guessing but this type of multi-select using the shift key usually works in windows)
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