First, preheat oven to 350° Fahrenheit. Line two cupcake pans with paper cupcake liners, then set aside. In a large bowl, whisk together the eggs, oil, sugar, sour cream, vanilla, and milk until smooth. Then whisk in the flour, almond meal, salt, baking powder and baking soda, and cocoa powder until combined. Add in your crushed/chopped gluten free Oreos (I put a bunch of them - still with the filling in - in a ziplock and then use a rolling pin to crush them into small pieces). Stir the crushed cookies into the batter, then scoop the batter into the prepared cupcake pans. Each cup should be a little over 3/4 full. Bake for 22-26 minutes or until the tops of the cupcakes spring back with touched, and a toothpick inserted into the center of the cupcake comes out clean. Let cool completely before frosting.
While cupcakes are cooling, make the frosting. First, scrape the filling out of about 15 gluten free Oreos (you can totally eat the filling now or toss it into your frosting). Place the dry cookies into a food processor or Nutribullet and blitz up until you have a fine cookie dust. Then, in a large bowl, using an electric mixer, beat the shortening, butter, and one cup of the powdered sugar until smooth. Add in the rest of the powdered sugar one cup at a time and beat until smooth. Add in 3/4 Cup of your powdered dry Oreo cookies to the frosting and beat together until combined. Add in the vanilla and the oreo filling if you want, and beat until smooth. Add a bit of cream if the frosting is too stiff to pipe, then scoop the frosting into a piping bag and frost cupcakes. Then serve!