I have tried both the .net FileUpload control and the ajax Asyncfileuploadcontrol to upload a file less than 500kb.
It seems that when I tried to go through my wireless router (att.bellsouth) that the uploads always fail, however when I plug my droid into my laptop and use my pda connection it works perfectly fine.
I'm wondering if the network connection from my house to my server could be causing this issue, and if anyone had any solutions to this problem. Tomorrow I'm going to try and upload from other networks and pray it works.