Hello Jorn,
Currently, Silverlight can access files only through OpenFileDialog or as out of browser application with elevated trust. Uploading a memory stream directly is currently not supported with the RadUpload.
Assuming that you have a collection of FileInfo objects, you can wrap them into RadUploadSelectedFiles and add them in the RadUpload.CurrentSession.SelectedFiles collection and ready them for upload.
Sincerely yours,
Alex Fidanov
the Telerik team
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