I upgraded a friend a few weeks ago for a flight tomorrow with my RPU. When I did it, the first segment was so full, the system would not even waitlist (nor an agent). The website actually gave a wrong error message saying there is no F on the plane but that is another story. So, only the 2nd segment showed Upgrade Requested.
Today, I called and the agent was able to waitlist him manually on the 1st segment and it show R Class Requested. I hope he will be able to check in online without problems.