Preheat the oven to 350 degrees F. Line a muffin tin with cupcake liners.
In a bowl, mix together the flour, baking powder, baking soda, and salt together. Set aside.
Beat ½ cup butter and sugar until light and creamy. Add in the egg and beat well. Add in the yogurt and beat well again. Alternate between adding the flour and milk in three additions, beginning and ending with the flour. Fold in 2 teaspoons of vanilla and a little over half of the crushed Oreos..
Place an Oreo at the bottom of each cupcake liner. Evenly divide the batter among the liners over the Oreos. It may seem as thought he liners are over filled, but they will be okay.
Bake for about 18 - 20 minutes, or until the tops spring back when gently touched. Take out and allow to cool completely.
Beat ½ cup butter until smooth and creamy. Slowly add 2 ½ cups of powdered sugar to the butter, one cup at a time until well incorporated. Add in the remaining vanilla.
Top the cooled cupcakes with the frosting. It doesn't have to be very neat. Place the remaining crushed Oreos in a bowl and dip the frosted cupcakes into the bowl carefully so as to coat the frosting.
Beat the heavy cream until soft peaks form. Add in the remaining powdered sugar and beat in. Pipe the heavy cream on top of each frosted cupcake using a star tip. Finish by inserting an Oreo into the top of the cupcakes.
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