Chocolate Coffee Cupcakes with Red Velvet Pudding Filling

For the basic pudding mix:

• ½ cup cornstarch

• 1 cup all-purpose flour

• 1 ½ cups granulated sugar

• 1 teaspoon salt

For the red velvet pudding:

• 3 cups whole milk

• ¾ cup Basic Pudding Mix (recipe above)

• 4 tablespoons cocoa powder

• ¼ cup granulated sugar

• 2 large eggs

• 2 tablespoon butter

• 3 teaspoons vanilla extract

• 4 teaspoons red velvet bakery emulsion

For the cupcakes:

• 10 ounces semisweet chocolate

• 4 cups cake flour

• ½ cup cocoa powder

• 3 teaspoons baking soda

• 1 teaspoon salt

• 1 cup buttermilk

• 4 teaspoons vanilla extract

• 4 cups firmly packed dark brown sugar

• 4 sticks salted butter, at room temperature

• 6 large eggs plus 2 egg yolks, at room temperature

• 2 cups brewed Catbird Coffee Roaster’s coffee, Black Cat, very hot

For the frosting:

• 1 cup unsalted butter, softened

• 2 teaspoons vanilla extract

• ¾ teaspoon salt

• ½ cup dark cocoa powder

• 4 cups powdered sugar

• ¼ cup heavy whipping cream

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Optional decorations:

• Crushed Oreo cookies, cream removed

• Gummy worm candy

• Reese’s cups, Halloween pumpkin-shaped, refrigerated

• Writing icing

• Sprinkles

Adapted from Dessert for Two & Tastes of Lizzy T

1. Make the Basic Pudding Mix: Combine the corn starch, flour, sugar and salt. Mix well and store in an air tight container. Set aside.

2. Make the pudding: Pour 2 1/2 cups of milk in a medium saucepan. Turn the heat on the stove to low. Allow the milk to get steaming and hot, but not boiling.

3. While the milk is heating, take another bowl and mix together the other half cup of milk with the pudding mix, cocoa powder, sugar and eggs.

4. Once the milk is hot, add the cocoa mixture to the hot milk and stir. Then add in the butter, vanilla, and red velvet emulsion.

5. Turn the heat up just a bit to medium or medium-low. Stir constantly because the mixture could easily burn.

6. Cook and stir until the pudding mixture starts to thicken, about 8 minutes, depending on the thickness you'd like. When the pudding is at a thick consistency, turn off the heat and remove the pan from the burner. It will thicken a bit more as it sits. Cool the pudding completely and refrigerate in an air-tight container.

7. Make the cupcakes: Position an oven rack in the center of the oven and preheat the oven to 350℉. Line 24 muffin cups with paper liners. 

8. In a microwave, melt the chocolate, stirring at 30-second intervals until just melted, about 2 minutes. Let cool until tepid but still fluid.

9. Sift the flour, cocoa powder, baking soda, and salt in a medium bowl. In a measuring cup, stir together the buttermilk and vanilla. In a large bowl, beat the brown sugar and butter with an electric mixer until the mixture is pale and fluffy.

10. Slowly, beat in the eggs and yolk. Beat in ⅓ of the flour mixture, followed by ½ of the buttermilk mixture. Repeat until flour is gone. Add the melted chocolate mixture. Gradually beat in the hot coffee.

11. Transfer the batter to the muffin cups, filling them about ⅔ full. Bake the cupcakes for 22-27 minutes, until a cake tester comes out clean. Let cool in pan for 5 minutes, then transfer to wire rack to cool completely.

12. Using a knife, cut a small hole in the center of the cupcakes, or use a cupcake corer.

13. Fill a piping bag with the red velvet pudding and fill the hole in the cupcakes with pudding until even with the top of the cupcake.

14. Make frosting: Beat the butter, vanilla, and salt until creamy.

15. Slowly add the cream, a little at a time, while continuing to mix. Gradually add powdered sugar, then the cocoa powder.

16. Beat on high for 3-4 more minutes until the frosting is light and fluffy. Frost the top of the cupcakes.

17. Decorate the cupcakes: Cut Reese’s cups in half. Use the writing icing to add spooky sayings, like “RIP” or “BOO”. 

18. Add crushed Oreo “dirt”, gummy worms, sprinkles, and Reese’s cup “headstones”. Enjoy!