I often in my developer need come across someone who needs/wants to upload multiple files. In the past I had to resort to commercial solutions such aspuploader. But in version 4.5 of .Net Microsoft finally supports multiple file uploads right out of the box. If you couple that with a generic handler you can upload loads of files at once.
The original article that shows all the code can be found here: Uploading Multiple Files Using jQuery and Generic Handler in ASP.Net 4.5
Kudos to Nimit Joshi for sharing this.