Is there a way to add multiple files to a WebRequest to simulate the selection of multiple files by an enduser?
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There's no built-in mechanism for this. You will have to implement it manually.

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Darin Dimitrov
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Any idea how you would do that? Or links on this subject? – Lieven Cardoen Dec 18 '09 at 09:23
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Follow the link over the `implement` word in my post. – Darin Dimitrov Dec 18 '09 at 09:24