Cookies and Cream Cake (or Cupcakes)

Cupcakes:
1 cup flour
1/3 c. unsweetened cocoa powder (Dutch process or regular)
3/4 t. baking soda
1/2 t. baking powder
1/4 t. salt
1 cup milk
1 t. apple cider vinegar
3/4 c. sugar
1/3 cup canola oil
1 t. vanilla extract
1/2 t. almond extract, chocolate extract or more vanilla extract
10 Oreos, coarsely chopped

Frosting:
1/2 c. shortening
1/2 c. margarine (I used butter)
3 1/2 c. confectioners' sugar, sifted if clumpy
1 1/2 t. vanilla extract
1/4 cup milk
5 Oreos, finely mashed, plus 6 of the cookies, cut in half, for garnish (I only used 2 for the crushed topping on the cake)

For the cupcakes: Preheat the oven to 350 degrees and line 12 muffin cups with paper or aluminum foil liners. For the cake: double the recipe. Preheat oven to 350, and grease a 9x13 pan.

In a medium bowl sift together the flour, cocoa powder, baking soda, baking powder and salt. Set aside.

In a large bowl, whisk together the milk and vinegar; set aside for a few minutes to curdle. Add the sugar, oil and vanilla extract and other extract, if using, and beat until foamy. Add the dry ingredients in 2 increments, and beat until no large lumps remain (a few small lumps are okay). Add the chopped cookies to the batter, stirring just to combine. (My batter was pretty liquid-y at this stage.) Spoon the batter into the liner cups, filling them three-quarters full. Bake for 18 to 20 minutes or until a toothpick inserted into the center comes out clean. For the cake, bake for 30-35 minutes or until a toothpick inserted into the center comes out clean. Transfer to a wire rack to cool completely.

While the cupcakes are cooling, make the frosting: In the bowl of a stand mixer or in a large bowl using a hand mixer, beat the shortening and margarine on medium-high speed for about 5 minutes, until well combined and fluffy. Reduce speed to low to add the sugar until incorporated, and then increase to medium-high speed to beat for about 3 minutes. Add the vanilla extract and milk; beat on the same speed for 5 to 7 minutes, until fluffy. Add the cookie crumbs, mixing well. (NOTE: I didn't double this for the cake. There was TONS. In fact, if I ever do the cupcakes, I might halve this as it makes more icing than I like.)

To assemble: Frost the cupcakes generously and top each cupcake with half of an Oreo by inserting the cut end into the frosting. Store in a sealed container for up to 3 days.