A good friend of mine (thanks again, Jay!) sent me this a long time ago and it’s still one of my favorite crowd-pleasing cupcakes to make, though a bit labor intensive. The recipe is from Bake It In a Cake and it’s a mini pumpkin pie baked inside of a vanilla cupcake with a cinnamon cream cheese frosting. It’s not too sweet and has a wonderful texture that is light though it appears dense. I had a lot of extra cupcake batter, pumpkin pie batter, and some pie crust so you may want to account for that to make more mini pies or even a small pumpkin pie and a few plain vanilla cupcakes. Enjoy!

Makes 24-26 cupcakes

Pumpkin Pies
1 (16-ounce) batch pie crust dough (2 one crust pies, you will have leftovers)
1 (15-ounce) can pumpkin pie filling, made as directed on the can (you will have leftovers)

Cupcakes
¾ cup (1½ sticks) unsalted butter, at room temperature
8 ounces cream cheese, at room temperature
1½ cups granulated sugar
3 large eggs
2 teaspoons vanilla extract
2 teaspoons baking powder
½ teaspoon baking soda
½ teaspoon salt
2½ cups unbleached all-purpose flour
1⅓ cups whole milk 

Frosting
2 tablespoons heavy cream or whole milk
1 cup cinnamon chips
1 cup (2 sticks) unsalted butter, at room temperature
8 ounces cream cheese, at room temperature
2 cups powdered sugar

Directions:

1. To make the mini pumpkin pies, preheat the oven to 425°F and lightly grease a 24-cup miniature muffin tin. Use a rolling pin to roll out the pie crust dough on a lightly floured smooth surface until the dough is about ⅛ inch thick. Then use a 2½-inch circular cookie cutter to cut out 24 small disks.
2. Press the dough circles into each cup in the prepared tin and fill three-quarters full with the prepared pumpkin pie filling. Keep in mind the pumpkin pie filling will expand a little while baking. Bake the pies for about 7 minutes. With the pies still in the oven, turn the oven down to 350°F and bake for an additional 7 to 10 minutes, until the edges of the crust have browned and the pumpkin pie filling no longer jiggles when you gently shake the tin. Allow the pies to cool for 5 minutes in the tin and then carefully transfer them to a wire rack to finish cooling while you mix the cupcake batter.
   

   

   
3. To make the cupcakes, line 2 standard muffin tins with 24 paper liners. Use a stand mixer fitted with the paddle attachment or a hand mixer on medium speed to combine the butter and cream cheese for about 90 seconds, until smooth. Add the sugar and mix on medium-high until fluffy. Add the eggs, one at a time, mixing in each egg completely before adding the next. With the mixer on medium speed, add the vanilla, baking powder, baking soda, and salt. Finally, add the flour, ½ cup at a time, alternately with the milk, ⅓ cup at a time, mixing until each addition is fully incorporated before adding the next. Continue to mix the batter on medium-high speed for 30 seconds, until smooth and creamy.
   

   

   

   
4. Spoon a heaping tablespoon of batter into each cup in the prepared tins. Place a cooled pumpkin pie into the center of the batter and press it gently. You don’t want the pie to touch the bottom of the tin. Cover the pies with another heaping tablespoon of batter so the top and sides of the mini pie are completely covered and the cup is about three-quarters full. Bake for 25 minutes, until the edges and tops of the cupcakes have turned golden brown and the cake springs back when you gently press your finger into the top of it. Allow the cupcakes to cool in the tins for at least 10 minutes before moving to a wire rack to cool completely.
   

   
   

   

   
5. To make the frosting, warm the cinnamon chips in a small microwave-safe bowl for about 20-30 seconds and stir the room temperature cream into the warmed chips until all the chips are melted. Using a hand mixer, cream together the butter and cream cheese on medium-high speed for about 30 seconds, until smooth. Whip in the powdered sugar, 1 cup at a time, until the mixture is fluffy. Finally, with the mixer on low, drizzle in the cinnamon chip mixture. (Make sure it has cooled a bit—if it’s too hot, it will melt the frosting.) Spread or swirl a generous helping of the frosting onto the cupcakes using a spatula or pastry bag.