Preheat the oven to 350°F (175°C) and line a cupcake pan with liners.
In a large bowl, whisk together the cake mix, eggs, oil, milk, sour cream, vanilla, and pumpkin pie spice until smooth and thick, about 1–2 minutes. Fold in the chopped cookies.
Fill each liner about 2/3 full and bake according to the package instructions, or until a toothpick inserted in the center comes out clean. Let the cupcakes cool completely before frosting.
For the frosting, beat the butter and cream cheese on medium speed until smooth and creamy, about 2 minutes. Add the powdered sugar and vanilla, beating until fluffy. Add heavy cream a little at a time until the frosting is light and spreadable.
Pipe a swirl of frosting onto each cupcake or spread with a spatula. Roll the edges in salted caramel crunch, then top with a whole or pumpkin sandwich cookie.