Preheat oven to 350°F. Spray two mini muffin pans with cooking spray (I like using the kind with flour for these pies).
Unroll your pie crust and cut 2 1/2” circles using a round cookie cutter. Press one into each mini muffin cavity. You should get about 18-20 with re-rolling the dough. Chill until filling is ready.
Whisk flour, baking powder, and salt in a small bowl. Set aside.
Whisk melted butter, sugar, and egg until thick and yellow (about 30 seconds by hand). Whisk in the vanilla extract.
Switch to a wooden spoon or spatula and add the milk and the dry ingredients alternately, stirring in between each addition.
Place 1 tablespoon of the batter in each prepared pie crust. You will have some batter left over; you can bake these in the remaining mini muffin tin cavities not being used for your pies (2 tablespoons per cupcake).
Bake mini shortcake pies for 10-13 minutes, until a toothpick comes out clean. Let cool before removing from the pan.
They should pop right out, but if needed you can use the tip of a knife to help ease them out.
Make the topping by placing the whipping cream in the bowl of a stand mixer and whipping on high using the whisk attachment. Add the powdered sugar and vanilla while mixing. Whip until peaks form (just a few minutes in a stand mixer; longer with a hand mixer).
Right before serving, place whipped cream in a pastry bag or gallon size ziploc bag and pipe onto each mini shortcake pie. (I used a 1M tip to make the swirls; just snip off the tip of the bag and insert the tip before adding the whipped cream.) Top with half a strawberry.
The whipped cream can be made a few hours ahead and stored in the refrigerator. I recommend cutting the berries close to when you are serving them. The mini shortcake pies (without their topping) can be stored in an airtight container for up to 3 days, or frozen for up to 1 month.