Preheat oven to 350°F. Spray an 8x8 or 9” round baking dish (with at least 2” sides) with nonstick baking spray.
Make the Crumble: In a bowl, combine all topping ingredients. Mix with a fork or hands until a crumbly mixture forms. Set aside.
Make the Cream Cheese Layer: In a small bowl, beat the cream cheese, powdered sugar, and vanilla until smooth. Set aside.
Make the Cake Batter: In a large bowl, beat together butter and coconut sugar for 3 minutes until light and fluffy. Add eggs, mashed banana, and vanilla extract. Mix until combined, scraping down the sides. Stir in dry ingredients: flour, baking powder, baking soda, salt, and cinnamon. Mix until just combined. Fold in pineapple tidbits, coconut flakes, and chopped pecans.
Assemble the Cake: Pour half the cake batter into the prepared baking dish. Spread the cream cheese mixture over the batter evenly. Sprinkle half of the crumble topping over the cream cheese layer. Add the remaining cake batter on top and gently spread. Finish with the remaining crumble topping.
Bake for 55–65 minutes or until a toothpick inserted in the center comes out clean. Cool in the pan for at least 30 minutes.
Make the Glaze: In a bowl, whisk powdered sugar with 2 teaspoons of milk. Add more milk as needed until the glaze is smooth and drizzable.
Finish: Drizzle glaze over the cooled cake. Slice and enjoy!
