If it's something I can fix as the user, I need good clear information.

If it's not something I can fix as the user, weigh the options: do I even need to know there's an error? Can you just cache the operation and try again later? Maybe an indication that it's happening in the background?

Current favorite peeve: Uber Driver app for deliveries complains "couldn't upload the photo" of the drop off. It's because this customer lives somewhere off the signal map. I can't do anything about it until I drive a mile back in the other direction. So, instead of blocking further operation, just hold that pic until we get back to civilization, ok? I need the map to get to the next pick up or dropoff, and this nonsense is in the way.