Preheat oven to 350 degrees. Line cupcake pan with cupcake liners. Set aside.
Hull and halve strawberries. Place in blender along with milk and blend until strawberries are pureed; no chunks. Pour into measuring cup, you want 1 cup of pureed strawberries/milk mixture. Set aside.
In a large bowl using an electric mixer, mix together boxed cake mix, oil, and eggs; mix until combined. Add vanilla extract; mix just until combined.
Mix strawberry Greek yogurt so that the fruit on the bottom is mixed into the yogurt, then add to the cupcake batter; mix until combined. Add 1 cup of strawberry puree/milk mixture; mix just until combined.
Scoop batter into cupcake liners - no more than ⅔ full, or use a #24 disher to scoop batter. Bake 13-15 minutes. Check cupcakes around 14 minutes to avoid over-baking. Insert a toothpick into the center of the cupcake, if it comes out clean, it is done. Remove cupcakes from oven and allow cupcakes to cool in cupcake pan for 2 minutes; transfer to wire rack and cool completely. Cupcakes should be cooled completely before frosting.
For Whipped Cream Frosting
Chill mixing bowl and wire whisk attachment in refrigerator for at least 20 minutes.¹
In a large bowl using an electric mixer with a wire whisk attachment, beat heavy whipping cream until desired level of firmness. Add in powdered sugar and vanilla extract until combined.
Pipe cooled cupcakes with decorating tip 1M or with your fav offset spatula. Garnish with strawberries. Eat & Enjoy!
Notes
Store Strawberries and Cream Cupcakes in an airtight container in the fridge; will keep for 2-3 days.¹ It's best to chill your mixing bowl and wire whisk when working with heavy cream and whipping cream, however, you can get away with not doing this.