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To make the cupcakes, preheat oven to 350F. Line 18 muffin cups with a paper liner. Set aside.
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In a mixing bowl, beat butter and sugar until light and fluffy. Add eggs, one at a time, and vanilla and beat until combined.
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In a separate mixing bowl, whisk together flour, baking powder, baking, soda, salt, and cinnamon. Add this mixture alternately with the milk and beat until just combined.
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Fill the prepared muffin cups ⅔ full. Bake for 17 - 20 minutes or until golden brown on top and a toothpick inserted into the center comes out clean. Cool completely on a wire rack before frosting.
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To make the frosting, put Cinnamon Toast Crunch in a food processor and process until cereal is crumbs.
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Beat butter with an electric mixer. Add in cereal and 1 tablespoon heavy cream. Beat until combined. If you want a thinner frosting, add another tablespoon of heavy cream and beat until combined. Frost cupcakes as desired and top with more Cinnamon Toast Crunch.