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Is a WA a "web agent" ? Just a curiosity, nothing crucial here.
Simple answer: you cannot.
detailed answer: you have to understand that using only html and javascript, you cannot make any file upload.
HTML is a page description language, a bit like xml.
You have to use a server side language (php, jsp, asp.net or whatever other technology) to handle your file transfer.
What html let you do, is to encapsulate the binary data of 1 file into a POST request field. So, if you need to upload 2 files, you need 2 <input type="file"> with different names.
That in mind, you can create an FORM request with the files embedded in javascript by using DOM functions (it's pretty easy even), but then, you will need to add something on your server to put the files with the right names at the right place and to re-create the directory structure.
The easiest way: create an archive on the local computer, send it to the server and unpack the archive using a server side language.
The C++ way: create a secured deamon on your server, listening to a port, and stream the datas to your deamon from your c++ app
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Listen to the ducky: "This is awesome!!!"
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