At least 30 minutes before baking, measure out the milk (85 grams, 6 tablespoons) and set it out with the eggs (2 large) to come to room temperature. Measure out the rest of the ingredients.
Position an oven rack to the center position. Preheat the oven to 350°F/175°C.
Prep an 8.5 x 4.5-inch (22 x 11-cm) loaf pan with parchment paper or non-stick spray.
In a large mixing bowl, whisk together the flour (210 grams, 1 ¾ cup), cocoa powder (20 grams, ¼ cup), dark brown sugar (200 grams, 1 cup), baking powder (10 grams, 1 tablespoon), salt (2 grams, ½ teaspoon), cayenne powder (½ teaspoon), and ground cinnamon (1 teaspoon).
In a separate bowl, lightly whisk together the eggs (2 large), milk (85 grams, 1 tablespoons), oil (113 grams, ½ cup), vanilla extract (2 teaspoons), and mashed ripe banana (480 grams, 2 cups).
Pour the wet ingredients into the dry ingredient bowl.
Stir with a spoon or silicone spatula until just combined. This should only take about 30-45 seconds of mixing. The batter will be pretty thick and lumpy. Do not over-mix or the bread will become tough.
Gently fold in 1 cup of the chocolate chips.
Pour into your loaf tin. Sprinkle the remaining ½ cup chocolate chips on top. Optional: garnish the top of the loaf with the sliced banana.
Bake at 350°F/175°C for 60-70 minutes until lightly golden brown and the top springs back when gently pushed or a toothpick inserted in the center comes out clean. Check on your bake at about the halfway mark, and if it looks as though it is not baking evenly, rotate the pan.
Transfer the baked loaf out of the pan onto a cooling rack about 10 minutes after taking it out of the oven. Let it cool for at least 20 minutes before slicing. This will help the texture of the bread to solidify.
Store uneaten bread covered in foil or plastic wrap at room temperature for up to 3 days.
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