Sites like Yousendit are offering payed uploads of up to 2GB. How is this done through a standard web form? or are they using something else?
My thoughts were that a standard input file field couldn't handle 2GB files to save its life.
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There is no reason a standard file input field couldn't handle files up to 2GB (above that, however, things may get tricky). Most servers, however, are configured by default with a fairly small hard limit, which is there to limit excessive resource usage.
What would kill you is the lack of any decent progress indicator for the user. Submitting a normal file input field will cause their browser to sit there for hours on end with barely any indication that the upload is even happening successfully.
This is where I've seen Flash come to help. There are many sites, like flickr and YouTube which use (or can be made to use) the Flash plugin to provide a friendlier uploading experience, including feedback that the upload is happening and even perhaps a progress bar.