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I have a list with a "New Item" form that has the built-in "Attach File" button at the top. If I want to upload I file then I can click on that button and I am taken to a page where I can choose the file using Windows Explorer browsing. However, this only allows me to attach one file at a time. If I would like to attach multiple files then I have to click on the "Attach File" button, choose another file, and repeat this process for every other file that I have.

Obviously it would have been better to just allow the user to attach all their files with one fell swoop of the Windows Explorer browser but the SharePoint development team did not include that. Does any one know of an alternative solution using perhaps a custom column with a file selector allowing multi-file selection?

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The telerik silverlight upload control in 2010 should do it, or you can create your own.

There are a few tutorial on how to make one in silverlight floating around the web.

The basic answer is SilverLight, the OOTB one relies on ActiveX from office 2010.

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