Preheat oven to 350°F (180°C) and line a muffin tin with paper liners.
Place the bananas on a baking sheet lined with parchment paper and roast for 15 minutes, or until softened and caramelized.
In a bowl, whisk together the flour, baking powder, salt, and cinnamon.
In another bowl, cream together the softened butter and brown sugar until light and fluffy. Beat in the eggs and vanilla extract.
Mash the roasted bananas with a fork and add them to the egg mixture.
Gradually mix in the milk, then gently fold in the dry ingredients.
Stir until just combined, then fill the muffin liners about ¾ full.
Bake the muffins for 18-20 minutes, or until golden brown and a toothpick inserted into the center comes out clean.
Meanwhile, prepare the frosting: Beat the cream cheese and powdered sugar until smooth. Add the heavy cream and roasted banana puree, and mix until creamy.
Let the cupcakes cool completely, then frost with the banana cream and drizzle with caramel sauce.
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