Bill Zebub
“It’s probably Matt Mercer’s fault.”
You only tend to see that when the risk of making things worse is higher than the chance of making them better really. I.e. fumbles where the fumble will drag the situation down and has a relatively large chance of happening. And if its too high it just discourages wanting to do it at all.
Yes. The trick is getting the balance right, so that it's a non-obvious decision in either direction.

