As far as I can remember, you either need to have artwork embedded in your music files or copy the artwork as a "folder.jpg" into the album folder on the walkman. (The latter only works if you have each album in a separate folder).
Use SONY media manager. highlight all the songs at the source and drag and drop the album picture at its place, it will show up. than you transfer it to the device. alternatively you can use an id3 tag editor and add the picture there. and transfer after.
Probably not the quickest way but I use itunes to edit the id3 tag. Copy the artwork from amazon.com, highlight the songs on itunes, right click and select get info, then paste the artwork into the artowrk box and select ok.
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