Preheat oven to 375 degrees F and line a cupcake pan with liners and set aside.
Combine all of the cupcake ingredients in a stand mixer and beat until combined.
Fill cupcake liners ½ - ¾ full, just slightly less than 1/4 cup of batter in each liner.
Reduce heat to 350 degrees F and bake for 18-22 minutes until toothpick comes clean from center.
Remove from oven and move cupcakes to cooling racks to finish cooling before frosting.
Begin preparing the frosting by adding the freeze-dried strawberries to a food processor and pulse until a fine dust forms.
In a large bowl or stand mixer fitted with a whisk attachment, beat the heavy cream, powdered sugar, and pudding mix on medium-high for about 2 minutes. Add in the freeze-dried strawberry powder and beat until light and fluffy.
Pipe the strawberry frosting onto chocolate cupcakes and garnish with sprinkles or fresh strawberries, if desired.