Preheat oven to 375°.
Prepare cake mix according to package directions. Stir in vanilla.
Place 33 foil muffin cup liners on a large baking sheet, or place in muffin cups. Divide batter evenly among muffin cup liners, filling about two-thirds full.
Bake at 375° for 17 to 18 minutes or until cupcakes are golden brown and cracks in cakes appear dry.
Cut a deep slit in top center of each cake to form a pocket. Gently tuck a chocolate kiss into each warm cake.
Combine sugar and coffee granules in a bowl. Add half-and-half and Kahlúa; whisk until smooth. Spoon 1 tablespoon frosting over each cake. Combine cocoa and cinnamon; dust evenly over tops of cakes.
Oxmoor House Healthy Eating Collection
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