Preheat the oven to 350°F (175°C) and line a muffin tin with cupcake liners.

In a mixing bowl, whisk together the flour, sugar, cocoa powder, baking powder, baking soda, and salt.

In another bowl, cream the softened butter until light and fluffy. Add the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.

Gradually add the dry ingredients to the wet ingredients, alternating with the milk, and mix until just combined. Fold in the crushed cookies.

Divide the batter evenly among the cupcake liners, filling each about 2/3 full.

Bake for 15-18 minutes, or until a toothpick inserted into the center comes out clean. Allow to cool completely.

In a mixing bowl, beat the softened butter until creamy. Gradually add the powdered sugar, mixing on low speed until combined.

Add the heavy cream and vanilla extract, and beat on high speed until fluffy.

Fold in the crushed cookies until evenly distributed.

Once the cupcakes are completely cooled, frost each cupcake generously with the cookies and cream frosting.

Top with additional crushed cookies if desired.