What I would recommend is to handle this scenario with custom code. Once the connection is lost, the upload control would raise the FileUploadFailed event. You can check the error message to be sure that the server is not found and there is a problem with the connection. Then, you can save all of the not uploaded items and re-add then back in the upload
as new items in a new uploading session.
Please let me know if this would be acceptable for you or if you have further question on this approach.
the Telerik team
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