Prepare the cupcakes: Preheat the oven to 350°F. Line the wells of 2 cupcake pans with 18 paper liners, set aside.
Coarsely chop 10 Joe-Joe’s Cookies, set aside. In a medium bowl, prepare Vanilla Cake Mix according to package instructions. Add chopped cookies to mix and gently fold in with a rubber spatula until evenly incorporated, being careful not to over mix.
Evenly divide the batter into lined cupcake pan, filling each cup about 3/4 full. Bake for 16-18 minutes, rotating the pans halfway through baking, until a toothpick inserted in the center comes out clean. Remove from oven and allow cupcakes to cool completely.
Prepare the frosting: Combine the cream cheese, butter and vanilla in the bowl of an electric mixer. Beat on medium speed until smooth, 1-3 minutes, scraping down the sides of the bowl with a rubber spatula as needed. Blend in the vanilla flavor. Add the powdered sugar in half-cup increments and blend to desired sweetness and thickness.
Frost the cooled cupcakes, then garnish with Joe-Joe cookie halves and crumbs. Enjoy!