[jonex]

I like the idea of focusing on the key notion of wether the task will succeed or not. A challenge in these things are to design things such that users understand what is communicated, and you also want something that fits the style of the app overall.

Personally I'm a fan of progress bars that indicates actual progress rather than any estimates the developer though would be good to provide. But if getting-stuck probability could be hinted at it would be great.

Maybe, whenever the bar gets stuck, it can slowly start greying out based on the probability that it's completely dead? That way an attentive user can use this as a clue for when to reload and try again, while not breaking the previous behaviour or introducing too much confusing information.