I'm not sure, as I haven't done it yet, but I heard from other people that it does if you use the "click to print", can someone confirm this?
An alternative to this is within Paypal itself. Paypal has a "Multi-Order Shipping" feature, which is independent by itself [although you'll have to do a lot of copy and pasting, or use a CSV or TSV (comma/tab separted value)]
Go go the "auction tool" tab on the top, and on the bottom of that list is the "multiorder shipping" link. Click that and play around with it, you'll figure it out.
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