In a separate large bowl, combine the sugar and melted butter. Add in the egg whites and stir. Whisk in the milk, half-and-half, yogurt, and vanilla.
1¼ cups granulated sugar, 1 cup unsalted butter, 3 egg whites, ½ cup milk, ⅓ cup half-and-half, ⅓ cup plain yogurt, 2 teaspoons pure vanilla extract
Add the flour mixture to the wet mixture and stir just until incorporated.
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. If you feel that your buttercream is too thick, simply add the milk 1 tablespoon at a time. You may not need it at all.
3 cups powdered sugar, 1 cup unsalted butter, 1 tsp pure vanilla extract, ½ teaspoon kosher salt, 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 prepared vanilla instant pudding
Pipe an empty circle of vanilla buttercream around the edge of the cupcake about 2-3 layers high. Gently roll the buttercream through the strawberry Oreo mixture to coat. Lastly, spoon several sugared strawberry pieces into the middle of the buttercream. Serve and enjoy!
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Notes
Strawberries: 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 like a strawberry syrup that you can use to drizzle over the cupcakes once they are frosted.
Filling: If you want to have extra strawberry flavor, you can add 1 teaspoon of strawberry flavoring into the vanilla pudding as you are stirring it together.
Buttercream: 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.
Topping: 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.
Storage: Store strawberry shortcake cupcakes in an airtight container in the refrigerator for up to 4 days.