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Tested beta 2.4 version 2
There seem to be no way to upload multiple files in the image /file section.
This would be a higly wanted feature it not available I would like to make a feature request for it,
If it does exist please let me know how I could activate this, thanks in advanche!
I think if you install Uncle Cheese's modules DataObjectManager and SWFupload that it will do it for you.