Uploading a file to a website is a pain. Uploading lots of files to a website makes the UN list of known methods of torture. At tonight's ruby group meeting Dave South showed off SWFUpload. This has to be one of the best uses of Flash ever. Now to upload 50 files you just browse, select them and then up they go. Dave has a great write up on using SWFUpload with Rails here. You can also find SWFUpload along with help with implementing it on other platforms here.