Hi.

I will let someone else comment on your code.
(But remember, this is a help forum for Tomcat, which is the server side. It is not really a forum to help people write Java HTTP cients).

It looks like this is your first try at sending a file to a server.
So let me recommend something :

I would start by creating a simple HTML form with an <input type="file" ..>, and then make sure that it works using the form. (Because, to upload a file, you also need to have some special code on the server to receive it, and you had better make sure that that side is working first).

You can find an example here :
http://tomcat.apache.org/tomcat-6.0-doc/api/org/apache/tomcat/util/http/fileupload/package-summary.html
and maybe someone else can suggest more examples somewhere.

Then, once it is working with the form, attack the client side.
If you search a bit on Google, you will find several examples of how to do this 
right.
No need to re-invent the wheel.


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