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much as reading metadata on multiple files at once crashes winamp sometimes, so too does selecting a bunch, right clicking, and trying to upload to the cloud. so far, it seems to only send one at a time. but i am sure they want to let you cue up a whole batch. i just believe, given most peoples upload speed constraints, they will only upload one file at a time within any given batch. so if you want to upload xyz, you highlight the 3, tell it to upload, and then x goes, finishes, then y goes, finishes, and finally z goes. granted, i'm making assumptions here, hard to test with things crashing.
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