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Hi, I'm writing an iPad application that mimics a flash website I built. The site uses Flash file uploader to upload files from the user's filesystem to my tomcat server.

I understand that an iPad application can sync files via iTunes to a Documents folder. Given access to those files, how can I invoke a file upload of a selected file to the web.

A: 

From what I find in tomcats docs, the file upload just works like a standard HTTP file upload as a POST request with a multipart/mixed body. RFC1867

To construct such a request you could use ASIHTTPRequest or see this question

tonklon