This recipe for Inside Out Chocolate Cupcakes is the result of my long-standing love of whoopie pies. Whoopie pies have long been one of my favorite treats.  If you love whoopie pies, Hostess Cupcakes, or Ding Dong cakes you'll love these cupcakes.

My mom used to spoil my brothers and me by making huge batches of whoopie pies that would be waiting for us after school.  

Inside Out Chocolate Cupcakes

Inside-Out Chocolate Whoopie Cupcakes

These chocolate cupcakes have all of the things we love about whoopie pies.  They start with a moist and delicious chocolate cupcake. The chocolate cupcake is filled with the traditional whoopie pie cream filling and then that same cream filling is used as the frosting on top. 

You can't get any better than that. Yummy cream inside and outside!  That's why I call these cupcakes Inside-Out Chocolate Whoopie Cupcakes. 

Another way to think of these cupcakes is to imagine a Hostess cupcake where the cream filling has taken over and is both inside and on top of the cupcake.

The Reasons You Will Love Inside Out Cupcakes

Plenty of filling and frosting.  With filling inside and on top of the cupcake you'll have some in every bite.

The chocolate cupcake is moist and delicious on its own.  The filling takes it over the top.

The cupcakes look professional but are easy to fill and frost.

I can tell you that without a doubt these cupcakes will make a special treat for those in your life with a sweet tooth. 

These cupcakes will also be a hit at your picnics this summer.  Don't worry about the cream filling and frosting.  Cooking the ingredients makes the filling very stable.

How to Make Inside Out Cupcakes

Chocolate Cupcake Ingredients

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Preheat the oven to 350 degrees F.  Fill the cups of your muffins tins with paper liners.  

In a bowl, add the dry ingredients: cocoa, flour, sugar, baking soda, baking powder, salt.  Stir to combine.

With your electric mixer on low (I used my hand mixer for this) stir in the eggs, water, buttermilk, vegetable oil, and vanilla until combined.  Don't fret if you don't have buttermilk on hand.  Try this buttermilk substitute instead.

Mix on medium speed for about 2 minutes until the ingredients are fully combined and the batter is smooth.  

For uniform cupcakes, use a scoop to divide the batter into the muffin cups.  Bake for about 20 minutes on the center rack of the oven.  

The Cooling Cupcakes

Let cupcakes cool in the pan completely before filling and frosting them.

To Make the Filling

In a saucepan over medium heat, combine the milk and flour.  

The Whoopie Pie Cream Filling

Cook, stirring constantly until the mixture forms a thick paste. Let cool.

In a medium bowl, beat sugar and shortening until fluffy. Add vanilla. Add cooled flour mixture and beat until double in volume.  The filling will be smooth and creamy.

To Fill and Frost the Cupcakes

Use a pastry bag to squirt the whoopie pie filling into the center of the chocolate cupcakes.  It is easy to squirt the filling into the top of the cupcake.  

You'll be frosting over the top so no one will know how the filling was inserted.

Filling the Cupcakes with Cream Filling

Pipe additional whoopie pie filling on top of the chocolate cupcakes.

Inside Out Chocolate Whoopie Cupcakes

Moist, chocolate cupcakes are always a big hit.  Make them even better with the addition of whoopie pie cream filling and frosting.  So good!

Here are a couple of other cupcake recipes you may enjoy:
Boston Cream Cupcakes
Red Velvet Cupcakes

Lemon-Lime Cupcakes

Pumpkin Cupcakes with Cream Cheese Frosting

filled chocolate cupcakes, Hostess cupcake copycat,

dessert, cupcakes

American

Yield: 20 cupcakes

Author: Donna Urso

Inside Out Chocolate Cupcakes

Prep time: 40 MinCook time: 20 MinTotal time: 1 Hour

Delicious chocolate cupcakes filled and frosted with sweet, creamy whoopie pie filling.

Ingredients

• 3/4 cup unsweetened cocoa powder
• 1 1/2 cups all-purpose flour
• 1/1/2 cups granulated sugar
• 1/1/2 teaspoons baking soda
• 3/4 teaspoon baking powder
• 3/4 teaspoon salt
• 2 large eggs
• 3/4 cups buttermilk, shaken
• 6 Tablespoons vegetable oil
• 3/4 cup warm water
• 1-teaspoon vanilla

Filling and Frosting

• 1-cup milk
• 3 Tablespoons flour
• 1-cup solid shortening
• 1-cup sugar
• 1-tsp vanilla

Instructions

1. Preheat the oven to 350 degrees F. Fill the cups of your muffins tins with paper liners.
2. In a bowl, add the dry ingredients: cocoa, flour, sugar, baking soda, baking powder, salt. Stir to combine.
3. With your electric mixer on low (I used my hand mixer for this) stir in the eggs, water, buttermilk, vegetable oil and vanilla until combined.
4. Mix on medium speed for about 2 minutes until the ingredients are fully combined and the batter is smooth.
5. For uniform cupcakes, use a scoop to divide the batter into the muffin cups. Bake for about 20 minutes on the center rack of the oven. Cool completely.
6. Use a pastry bag to squirt the whoopie pie filling into the center of the chocolate cupcakes. It is easy to squirt the filling into the top of the cupcake. You'll be frosting over the top so no one will know how the filling was inserted.
7. Pipe additional whoopie pie filling on top of the cupcakes.

To Make the Filling and Frosting

1. While the cupcakes are cooling: In a saucepan over medium heat, combine the milk and flour. Cook, stirring constantly until the mixture forms a thick paste. Let cool.
2. In a medium bowl, beat sugar and shortening until fluffy. Add vanilla.
3. Add cooled flour mixture and beat until double in volume. The filling will be smooth and creamy.

Nutrition Facts

Calories

271.21

Fat (grams)

15.29

Sat. Fat (grams)

4.73

Carbs (grams)

31.17

Fiber (grams)

0.89

Net carbs

30.29

Sugar (grams)

21.29

Protein (grams)

2.71

Sodium (milligrams)

188.05

Cholesterol (grams)

16.38

Nutrional information is approximate.

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