Preheat the oven to 350 degrees Fahrenheit. Start with the bottoms of each of the molds first. Remove the cylinder inserts and set them aside. Scoop out about one teaspoon of dough and roll it into a ball with your hands.
Next, while holding the cookie dough ball in one hand, use the palm of your other hand to press and flatten the ball into a disk about ¼th an inch thick. The dough disk should fit on the bottom of each mold when laid flat. Place each dough disk into the bottom of each mold and press down slightly. Continue until each mold compartment has a dough disk inserted into the base.
Then, take about two teaspoons of the chocolate chip cookie dough at a time, and roll it into a ball again. Then flatten the dough into about ¼th an inch thick and press into the walls of the cookie shot mold, working your way up from the bottom. Continue until all the walls of the shot glass have been created and are about ¼th an inch thick.
Next, place the cylinder inserts in the dough-filled molds and press down evenly. Then, gently twist the insert upward and remove it. Inspect the inside of the cookie shots and patch any gaps or thin spots with small pieces of cookie dough as needed. If pieces need patching, you must press the insert in again. If no patching is necessary, place the insert exactly where it was without pressing again.
Bake the chocolate chip cookie shots at 350 degrees with the inserts for about 21-23 minutes.
Once done, working quickly, take a sharp knife and cut around the insert at the top of the mold, removing the excess dough that has puffed up over the top. Cutting away the extra dough creates a straight edge on the top of the glass. As the cookie dough cools, it will become more challenging, so working fast is essential.
Allow the chocolate chip cookie shots cool while still in the mold for about five minutes. Then remove the metal inserts and transfer the cookie shot mold to a wire rack, allowing it to cool completely.
Once the cookie shot molds are cool, take one finger and slide the inside walls of the cookie toward the top to remove them. They should slide right out. Once the cookie shots are entirely cool to the touch, they are ready to be lined with chocolate.