I think a good way of looking at it is risk. Is the change (whether it is code or configuration, etc.) worth the risk it brings on.

For example if it's a small feature then it probably makes sense to wait and keep things stable. But, if it's something that itself causes larger imminent danger like security patches / hard disk space constraints, then it's worth taking on the risk of change to mitigate the risk of not doing it.

At the end of the day no system is perfect and it ends up being judgement calls but I think viewing it as a risk tradeoff is helpful to understand.