Down by 4 in the 9th 1st 2 men reach Pesky flys out to right Dumb Hal decides that runner on 2nd should tag up and try to advance to 3rd He's out of course. Hal is a dope.
I've seen that more times than I would like. Sometimes it works for you and sometimes against. Still, it would be good for HAL to understand that in the 9th inning, there is a huge difference between the potential tying runner and the runner who could get you within two runs.
But virtually any baseball player if he had 95% odds of being safe would go. Most would go with lesser odds. I would say if you are not wanting to challenge in such situations your philosophy is very conservative with respect to baserunning and you should set your settings accordingly.