Preheat the oven to 325 degrees Convection bake or 350 degrees traditional bake. Prep three 6" cake rounds OR two 8" cake rounds with a swipe of shortening and dust of flour, or 24 cupcake tin with cupcake liners. Set aside.
In a food processor, add in the Oreo cookies and butter and pulse until a crumble forms. Divide crumble evenly between cake pans or cupcakes and press down firmly to make the crust. (Tip: I use the bottom of a measuring cup or glass to make an even crust). Set aside while making the cake batter. No pre-baking required for the crust.
In a medium bowl (not a stand mixer for this step), hand whisk together the sour cream, buttermilk, vegetable oil, eggs, egg white, and vanilla (also the caramel extract, if using) until uniform throughout.
Sift in the cocoa and cake mix, toss in the chocolate chips. Don't overmix – just whisk until the ingredients are barely combined. Divide evenly between cake pans or cupcake tins and bake for 27-30 minutes for cakes, and 12-15 minutes for the cupcakes. Let cool in the pan for 3 minutes, then flip out onto a cooling rack until room temperature. Wrap in plastic wrap and freeze for at least a couple hours or overnight until you're ready to stack the cake.