Preheat oven to 350 degrees F. Spray or lightly grease mini muffin pan/s (you'll need 24 cups.) Find a measuring spoon, shot glass, bottle top, small jar or other item that you'll be able to use to create a round cavity in the baked dough. It should be smaller than the cup, but not go all the way to the edge. Set aside. Test it out on the pan now, before you start the recipe, so you'll be ready when the time comes.
In a medium bowl, whisk together flour, baking soda and salt. Set aside.
With an electric mixer, beat butter for 30 seconds or until creamy. Add sugars and beat until fully combined, about 1 minute. Add vanilla and egg and beat until fully combined. Gradually add flour mixture and continue mixing until fully combined. Stir in mini chocolate chips until evenly distributed.
Using a measuring spoon, scoop out 1 Tablespoon of the cookie dough, roll it into a ball and place it into one of the cups of the prepared pan. Repeat until all 24 cups are filled with a ball of cookie dough.
Bake for 8-10 minutes or until edges are golden brown but the center is still light. Remove from oven and immediately use your measuring spoon, shot glass etc. to press firmly in the center of each cup creating a cavity for your filling. As the cookie cups cool, they will set and it will be difficult to press so make sure you do this right when they come out of the oven. Once every cup has been pressed, allow to cool in the pan for five minutes, then remove to a rack to finish cooling.
While the cookie cups are cooling, make the filling. Place peanut butter, butter and salt in a small, microwave safe bowl. Microwave until butter has just melted. Stir until combined. Add powdered sugar and stir until fully combined.
Spoon about two teaspoons of the filling into each cup and spread evenly. (It's not necessary to wait for the cups to be completely cool before filling.)
Melt the chocolate chips and shortening in the microwave, heating and stirring at 15 second intervals until fully melted. (Be careful not to burn the chocolate or it will seize up and you'll have to start over.) Spoon about 1 teaspoon of the melted chocolate over the peanut butter filling, using the back of the spoon to tap the chocolate, coaxing it to spread all the way to the inner edge of the cup. Refrigerate cups until chocolate is set. Serve chilled or at room temperature.
*Whenever I specify room temperature butter, I mean it to be soft enough to press your finger into it and leave an indentation. It shouldn't be so warm that it's lost any structure.
*Use measuring spoons to help you evenly distribute the cookie dough, peanut butter filling and melted chocolate. I ended up with just a little bit of peanut butter filling and a smattering of melted chocolate left over. I spread the excess peanut butter filling onto graham crackers and drizzled the bit of chocolate left over it. They made a nice, impromptu snack.
*Peanut butters are different and can have varied amounts of salt and sugar in them. I wouldn't change the amount of powdered sugar used because its amount is based on both sweetness and the texture for the filling. However, you may want to taste for salt. Salt can balance sweetness, so just make sure the filling tastes good to you.
*I generally prefer darker chocolates but wanted to go a bit sweeter for this recipe. I used about 3/4 milk chocolate chips and 1/4 bittersweet chips to make up my 1/2 cup. I don't think you can go wrong here. Just pick the chocolate you like best. Use just one or mix them up.
*Get creative when trying to find something to create the cavities in the cookies. I tried a bunch of different options, but the measuring spoon ended up working best for me. Remember, even if you use an empty pill bottle or other non-kitchen related item, you can cover it in a couple layers of plastic wrap so you can make "clean" cavities.
*I store these cups in the refrigerator. I always err on the side of conservative food safety/storage even though the filling ingredients supposedly can live at room temperature. I also prefer the texture of the filling when it's been chilled.
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