Preheat your oven to 350°F and grease 2 regular size (12 cup) muffin tins with nonstick cooking spray.

Roll each sugar cookie into a ball and place into the muffin tin. Gently press the dough into the pan and onto the sides using a tart shaper dipped in flour or the back of a spoon. Keep the bottom thin and the sides higher to create an edge on the crust.

Bake for 10-13 minutes or until golden brown. After baking, use a tart shaper or back of a spoon to gently press the crust so the divot in the center is more pronounced. Let the cookies cool completely in the pan before transferring them to a wire rack.

In a mixing bowl, whisk together the instant pudding mix, 1 cup of heavy whipping cream, and milk until smooth. Refrigerate this mixture.

In a microwave-safe bowl, heat the remaining 1/3 cup of heavy whipping cream for 30-45 seconds until hot but not boiling. Add chocolate chips and butter, then let it sit for 5 minutes. Stir the mixture until smooth.

Refrigerate the chocolate ganache for 5 minutes. Afterward, remove from the fridge, stir well, and return to the fridge. Set a timer for 5 minutes and stir after it goes off. Repeat this process for about 15-25 minutes until the ganache reaches a pudding-like consistency.

Use a tablespoon portion scoop to place vanilla cream onto each pie cookie. Use the back of a spoon to spread it onto the cookie, creating a small divot in the center to hold the ganache. Top each cookie with a dollop of ganache and let them set.

Refrigerate the cookies, loosely covered, until you're ready to serve.