Same thing has happened to me this year several times when checking in on the Android app. OLCI works, but checking the box for adding to the airport list results in an error message to add at the airport. I have stopped checking in on the app if the upgrade has not cleared yet.
Regarding your upgrade position being held based on original booking- true, but there is the additional hassle of making sure you get added at the airport on a timely basis. Missed an upgrade BWI-DFW this year on one of those Android errors. Very slow TSA, line at the gate to speak to an agent, so didn't get on the list until about T-40 when 2 names had appeared on the cleared list. Can't say if they were standby or upgrade though, and of course even if upgrade I may not have trumped them.