Preheat oven to 350* F. Spray a (24 count) mini muffin pans with baker’s spray. Set aside.
In a medium bowl sift together the all-purpose flour, cornstarch, baking soda and salt. Set aside.
In a large mixing bowl cream the butter, granulated sugar and light brown sugar, on medium speed with a handheld mixer or in a stand mixer fitted with the paddle attachment, for 2-3 minutes or until light and fluffy.
To the creamed butter add the egg, egg yolk and vanilla extract. Beat on medium speed until fully incorporated.
With the mixer on low, slowly add the flour mixture to the bowl and mix just until all the flour has been incorporated and no streaks remain.
Stir in the mini chocolate chips until evenly distributed.
Using a small cookie scoop (approximately 1 tablespoon) a level scoop of cookie dough and place into a mini muffin cup. Repeat until you have filled all the prepared mini muffin cups. Note, you will have to bake a second batch with the remaining cookie dough unless you have two, 24 count, mini muffin pans.
Bake for 9-11 minutes or until lightly golden and the canter has set.
Remove the mini muffin pan from the oven and allow the cookies to cool for 2-3 minutes.
Using the bottom of a small glass (a shot glass works well for this) to push the center of the baked cookies down while they are still warm to form the cookie cups. Be sure to use a small glass that is not as wide as the mini muffin cup openings so that you leave enough of the sides of the cookie cups intact for good structure for filling with the pudding.
Allow the cookie cups to continue to cool in the pan for another 8-10 minutes before removing them from the muffin pan and allowing them to cool completely on a wire rack before filling them.
While the cookie cups are baking and cooling, you can make the chocolate pudding. In a medium mixing bowl add the chocolate instant pudding mix and whole milk. Whisk for 2 minutes or until slightly thickened. Cover with plastic wrap and refrigerate.
Once the cookie cups have cooled completely, you can spoon 1 ½ tablespoon dollops of pudding into each of the cookie cups before plating and serving.
Notes
Be sure to use mini chocolate chips for these cookie cups. The standard sized chips are just too big for this recipe.
You can make larger cookie cups using a standard size muffin pan. You will need to add about 2 ½ - 3 tablespoons of dough to each muffin cup and adjust the bake time to 15-17 minutes.
The pudding for these cookie cups is made with less milk than called for on the package to make this a thicker pudding consistency. You can certainly make the pudding according to package directions if preferred.
You can transfer the thicker chocolate pudding to a large piping bag, fitted with a large piping tip, to pipe the pudding into the cups in a more decorative manner.
You can use whatever flavor or instant pudding you prefer to fill your cookie cups. Vanilla works well with the chocolate chip cookies. You can do a combination of both chocolate and vanilla filled cookie cups if desired.