Make the chocolate ganache first: Place chopped chocolate in a medium heat-proof bowl. Heat the cream in a small sauce pan over medium heat just until warm, do not let it boil! Pour warm cream over chopped chocolate and let it sit for 3-4 minutes. The warm cream will melt the chocolate. Then, whisk until smooth and creamy. Place in the fridge.
4 oz. high-quality dark chocolate bar, chopped, 4 oz. heavy cream
Make the peanut butter filling next. In a medium sized microwavable safe bowl, melt the peanut butter, powdered sugar, butter and salt for ~1 minute, or until ingredients are melted. Stir with a spoon to combine and set aside.
1/2 cup creamy peanut butter, 1/2 cup powdered sugar, sifted, 1 Tbsp. unsalted butter, pinch of salt
Preheat the oven to 400°F. Make the cookie dough in a stand mixer or using a hand mixer.
1 batch Kroll's Kookies cookie dough, leave out the chocolate chips
Prepare the cookie dough cups. Place liners in a muffin tin (I love using silicone liners). Use a cookie scoop to scoop out the dough and press the cookie dough into the muffin tin. Use your fingers to make a well and press cookie dough up the sides of the cup. (if the dough is sticky you can use a little flour on your fingers to help) Bake for 10-12 minutes, edges will begin to look golden brown.
While cookie cups are baking, every couple minutes you will need to use the back of a wooden spoon, fondant rolling pin, handle of a cookie scoop (or something similar), to keep the cup shape. (See video for reference). I recommend pressing the dough down about half way through, and once more before you scoop the fillings in the center. It might look wonky at this point but trust the process.
Once cookie cups are done, spoon peanut butter layer on first followed by the chocolate (about 2 tsp. peanut butter and 1 Tbsp. of the chocolate ganache).
Enjoy immediately or if chocolate needs to firm up, place in fridge for ~1 hour. Then bring cookies to room temperature and enjoy. Can store in the freezer for up to 2 months.