Preheat the oven to 350°F. Spray a 12 cup muffin pan with nonstick spray.
For the glaze:
In a medium-sized bowl, whisk together powdered sugar, heavy cream, and vanilla extract until smooth. Set aside.
For the cookie cups:
Add 2 cookie’s worth of dough to each cup of the pan. I smush the two cookie dough pieces together and roll them around to make a ball before placing into the muffin tin.
Use the back of a tablespoon (or your fingers) to create a depression in the center of the cookie cups.
Bake the cookie cups for 10 minutes.
Remove the pan from the oven and use a shot glass or similar item to help create an evenly shaped depression into each cookie cup while they’re still hot.
Add one tablespoon of strawberry pie filling to each cookie cup.
Return the pan to the oven and bake for an additional 5 minutes.
Remove the pan from the oven and allow cookie cups to cool just enough to become firm.
Gently remove each cookie cup using the blade of a butter knife. Place on a cooling rack or parchment paper.
Drizzle each cookie cup with the glaze that was made earlier and serve.
Notes
You can use any pie filling that you'd like for these!
Change up the cookie dough to change the flavor. Chocolate or snickerdoodle would be great.
If you can't find a 24 count package a 12 count will work. If the 12 count cookies are individually larger in size than the 24 count cookies then you may not need a second package. If not, buy two packages.