There are several factors I would cross-check in this case:
1.) Connection Validation:
Perform a netstat -ano | find "1344" to identify whether: (a) there is port listening on the Web Prevent on 1344 & (b) there is a active Proxy-WebPrevent session in "ESTABLISHED" state.
2.) Traffic Validation
Once the connection and active data transfer is verified - install & run packet capture (I would run wireshark) with a IP/Port filter to identify that we are receiving traffic from the proxy
3.) Type of Traffic Validation
We know there is traffic however we need to ensure that the same is not encrypted or traffic under some kind of an unsupported encapsulation. This could be verified by simply examining the wireshark packet. You could even go to an extent of searching the "confidential keywords" you are attempting to upload for testing in wireshark. Ideally just the "find option" in wireshark works else you could also try tcp contains testkeyword in the filters section of wireshark.
4.) Policy Application and other checks once we know the right traffic is reaching the Web Prevent Servers.