Preheat & Prep: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
Mix Dry Ingredients: Whisk together the flour, baking soda, salt, and cinnamon in a medium bowl.
Cream Butter & Sugar: Beat the softened butter and brown sugar with an electric mixer until light and fluffy.
Add Wet Ingredients: Mix in mashed bananas, egg, and vanilla extract until fully combined.
Combine Mixtures: Gradually add the dry ingredients to the wet mixture. Stir in chocolate chips.
Prepare Espresso Swirl: Dissolve espresso powder in hot water. Mix with powdered sugar to form a smooth glaze.
Scoop Dough: Drop tablespoon-sized scoops of dough onto the prepared baking sheet, leaving space between each cookie.
Add Espresso Swirl: Drizzle a small amount of the espresso glaze over each cookie and swirl gently with a toothpick.
Bake: Bake for 10-12 minutes or until the edges are golden and the center is set.
Cool: Allow cookies to cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.