Soft cinnamon roll cupcakes with a buttery brown sugar swirl baked right in and finished with a sweet vanilla glaze. All the cozy flavor of classic cinnamon rolls in an easy cupcake form.
Line a muffin pan with cupcake liners and preheat the oven to 350°F.
In a small bowl, combine the brown sugar, cinnamon, melted butter, and flour. (I use a glass measuring cup) Stir until fully combined and smooth. The mixture should be thick but pipeable.Transfer the filling to a pastry bag fitted with a round tip, or to a zip-top bag with a small corner snipped off. Set aside.
In a large bowl, mix together the cake mix, pudding mix and cinnamon. Add the eggs, oil, milk, and butter vanilla emulsion. Mix just until smooth. The batter should be thick but scoopable.
Fill each liner about ⅔ full with batter. Avoid overfilling.
Pipe about 1 tablespoon of the cinnamon filling into the center of each cupcake. Start in the middle and pipe a tight spiral, stopping before you reach the edges.
Place the filled pan in the refrigerator for 10 minutes. This helps control spreading and encourages a taller, domed top.
Bake at 350°F for about 15 minutes, until the tops are set and spring back lightly when touched.
While the cupcakes are baking, whisk together the powdered sugar, milk, and butter vanilla emulsion until smooth. The glaze should be thick but pourable. Adjust with a few drops of milk if needed.
Let the cupcakes cool in the pan for 10 minutes, then transfer them to a wire rack to cool completely. Spoon the glaze over the tops, allowing it to naturally settle into the cinnamon roll swirl.
Notes
Avoid over-swirling to keep the cinnamon layers defined.
Let cupcakes cool completely before glazing to prevent soaking.