In games that use permadeath, such as a Nuzlocke run of Pokemon or any Fire Emblem run, I'm always terrified and expecting the worst even when I dramatically overpower the enemy.
Also, despite colossi actually being quite weak in Shadow of the Colossus, I really, really, really, really tried my hardest to avoid unnecessary danger.
On PvP servers on World of Warcraft, I am always paranoid despite outnumbering the enemy faction 20 to 1 (lol Mal'Ganis), being max level and relatively skilled at PvP, and being able to fly away from any danger with an instant cast.