When innocently playing Oregon Trail, when one of your party members manages to magically break their leg while calmly riding in a wagon. Other incidents include your wagon falling apart while crossing a river, firing wildly in circles while hunting and missing every target, or another party member instantly dying from some horrible disease.
1) Man, what the fuck? My entire wagon exploded like 3 feet from shore. I just Oregon Failed.
2) "you shot 18 animals for 12563 pounds of meat. However, you can only fit 12 more pounds into the wagon" "Wow, Oregon Fail."
3) Ok, Jess just died of dysentery for some reason. What an Oregon Fail.