I have been working on a flex uploader, where the user can select multiple files.
It works fine when the files are uploaded in a queue (one at a time), however as so
The problem is with the model in which Flex connects to the back-end. With HttpService and Remoting, Flex clients opens a Http connection to the server. If you are connecting to the same Servlet / service on the server, it will use the same connection and can run into issues.
For a simple test, try create two instances of the same servlet and send upload requests to 2 servlets for 2 uploads. It should work.