I had a fielding cap increase with a challenge of commit no errors in the next three games. I then play the next three games with no errors then it says challenge failed. Like WTF!!!
I've had that happen before. I think if you don't have it set to do every play, he could potentially commit an error during sim.
It just happened to me again. I sent in a bug report on it. If we are going to have challenges then at least give us what we earn. I have it set on all fielding plays.