Quote Originally Posted by WoF View Post
If the web service only accepts a single POST command, splitting up is not an option.
While it is true that there'd only be a single POST command, there would be many packets of data for a file of the size in question.

The Winsock control has a SendProgress event. I'd think this could be used to collect additional chucks of data from the file to be sent. I've not used the inet control, so I don't know if it offers something of this sort.

The POST command includes the total length of the data being sent, so the server would be expecting more if only part of it were sent. It's been awhile since I had to deal with this, so I'd probably use a packet sniffer to see what handshaking goes on between client and server during an upload.