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In a medium bowl, mash ¼ cup of overripe banana until smooth.
Add ¼ cup vegetable oil or melted butter and ⅓ cup light brown sugar. Whisk until blended and glossy.
Whisk in 1 egg yolk and ½ teaspoon vanilla extract until smooth and cohesive.
In a separate bowl, whisk together flour, baking soda, cinnamon, and salt.
Fold dry ingredients into wet ingredients just until combined.
Fold in chocolate chips.
Let dough rest for 15–30 minutes at room temperature or chill up to 24 hours.
Preheat oven to 350°F (175°C) and line baking sheet with parchment paper.
Scoop tablespoon-sized mounds of dough onto sheet, spacing apart.
Bake 8–10 minutes until edges are set and centers still look soft.
Cool on pan 5 minutes, then transfer to wire rack.