Preheat oven to 350°F. Line a cupcake tin with liners and set aside.
Mix the cake mix, water, butter, and eggs in a medium bowl.
15.25 ounces vanilla cake mix, 1 cup water, ⅓ cup unsalted butter, 3 large eggs
Fill the cupcake liners ¾ full of batter and place into the oven to bake for 15-18 minutes or until a toothpick inserted comes out clean or with moist crumbs. Once baked, remove from the oven and place onto a wire rack to cool.
For the Strawberries:
In a small bowl, combine the chopped strawberries and sugar to allow the sugar to sweeten the strawberries. Set aside.
1 cup chopped strawberries, ⅓ cup granulated sugar
For the Buttercream:
Combine all of the buttercream ingredients except the milk in the bowl of a stand mixer fitted with a paddle attachment. Beat on low for 1 minute to allow the powdered sugar to become incorporated. Increase the speed to high and beat for another 3-4 minutes, or until a fluffy, smooth frosting has formed. Add the milk, if needed, to thin the consistency.
3 cups powdered sugar, 1 cup unsalted butter, 1 teaspoon pure vanilla extract, 2 tablespoons milk
Fill a piping bag fitted with a star tip with buttercream and set aside.
For the Topping:
Add the crushed Oreos, strawberry Jell-O, and a dot of pink food coloring to a small bowl. Stir until it is completely mixed and the Oreos have begun to turn somewhat pink.
Once the cupcakes are cooled, use a piping tip or an apple corer to remove the center of each cupcake. Place that piece of cupcake to the side, but do not discard it.
Fill a piping bag with the prepared vanilla pudding. Fill the empty centers of the cupcakes with vanilla pudding just below the top edge of the cupcake. Replace the piece of cupcake that you took out of the center and push it down into the vanilla pudding to hold it in.
½ cup ready-to-eat vanilla pudding
Pipe an empty circle of vanilla buttercream around the edge of the cupcake about 2-3 layers high. Chill the cupcakes for 10 minutes to firm up, then gently roll the buttercream through the strawberry Oreo mixture to coat. Lastly, spoon several sugared strawberry pieces into the middle of the buttercream before serving.
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Notes
*White or yellow cake mix also works great.**I don't recommend using frozen strawberries for this recipe because they will release too much moisture once they thaw, leaving you with soggy cupcakes.***Vanilla wafers or graham crackers work, too.****For a healthier swap, use pulverized freeze-dried strawberries.Tips:
If you let the sugared strawberries sit for about 10 minutes before frosting your cupcakes, the sugar will begin to melt, and you will have a strawberry syrup. Strain the strawberries through a fine-mesh sieve before spooning them into the center. Reserve that syrup to drizzle over the cupcakes just before serving.
When making the buttercream, the longer you whip it, the fluffier it will become as air becomes incorporated. However, over-whipping your buttercream can cause it to separate. The longest I usually like to whip buttercream is about 6-8 minutes.
If you are having a hard time getting the Jell-O and food coloring to combine with the crushed Oreos, do not be afraid to get in there with your hands and break up the Jell-O and food coloring pockets with your fingertips.
If you want to have extra strawberry flavor, you can add 1 tsp of strawberry flavoring to the vanilla pudding as you are stirring it together.
Ensure your cupcakes are completely cold before coring them, or the pudding will melt into the cupcakes.
If your pudding is watery, stir in 1 tbsp of powdered sugar to thicken it up.
Make-Ahead: You can bake the cupcakes up to 2 days ahead, wrap them in plastic wrap, and store at room temperature until ready to fill and frost.Storage: Store strawberry shortcake cupcakes in an airtight container in the refrigerator for up to 4 days.