In a large mixing bowl, use a hand mixer to beat together shortening, brown sugar, and sugar until mixture is fluffy.
Add in the egg, vanilla extract, and salt and mix until smooth.
Use a large spoon to stir in flour. Mixture will be really crumbly, but should hold together when pressed. Stir in 1 cup mini chocolate chips until combined.
Scoop mixture into popover pan and press to the bottom and sides, making sure to leave a hole in the middle for the milk to go later. You only need the sides and bottom to be about 1/4 inch thick. It's hard to get it much thinner.
Bake in the preheated oven for 18-20 minutes until cookies get a golden brown kiss.
Carefully remove the cookies from the popover pan. This can be done by placing a large cutting board or pan over the popover sheet and flipping it over. Gently tap the bottoms of the popover cups to loosen. Let cool completely.
Carefully melt the remaining 1 cup of chocolate chips in a microwave safe bowl by microwaving for 15 seconds at a time, removing and stirring, until chocolate is melted.
Coat the holes in the cookie cups with the chocolate. Drizzle some in and swirl, or if your chocolate is on the thicker side just give it a good smearing.
Refrigerate until chocolate is set. Serve by filling the "cups" with milk and enjoy!