Toss the butter and both kinds of sugar into a mixing bowl. Beat for a couple of minutes until it is light and creamy. Add the eggs and vanilla and beat well.
In a separate bowl, combine the flour, salt, and baking soda then gradually add the flour mixture to the butter mixture. The dough will be thick and stiff.
Stir in the mini chocolate chips. For best results, refrigerate the dough for one or two hours.
Pre-heat the oven to 350°F while the cookie dough chills.
Pack balls of chilled cookie dough into the cookie shot mold. Press the inserts into the center of each mold. Some cookie dough will push up and out of the mold. Leave the inserts in place and scrape the excess cookie dough away.
Bake for 20 to 22 minutes. Halfway through the baking time, use an oven mitt and push the inserts down again. Cookie dough will expand out of the mold as it bakes but you can remove the excess later.
When the baking time is finished, let the cookie shots cool for a few minutes so you can handle the mold without getting burned. While the cookie shots are still warm and with the inserts still in place, scrape away the excess cookie dough that expanded out of the mold while baking.
Now let the cookie dough cool completely. (Keep the inserts in until the cookie dough is cool.)
Once the cookie dough is cool, twist the inserts and lift them out of the mold. Next, twist the cookie cups and lift them out of the mold. Set the cookie cups aside while you prepare the chocolate coating.
Prepare the chocolate coating:
To melt the chocolate in the microwave place it in a microwave proof bowl and melt it in 20 to 30-second intervals, stirring in between.
To melt the chocolate in a water bath, simmer some water then turn off the heat. Put a bowl of the chopped chocolate over the hot water and just let the chocolate sit for several minutes.
Whatever method you use, don’t rush the melting process or it will get thick and clumpy. Chocolate that melts slowly will be smooth and easy to work with.
Coat the inside of the cookie shots:
Pour a little melted chocolate inside the cookie shot glasses then use a clean paintbrush to thoroughly coat the inside cavity of the cookies.
Turn the cookie shots upside down and dip the tops of them into the chocolate then set them aside until the chocolate is completely set.
After you coat all the cookie shot glasses, go back and inspect them for any areas that did not get coated well. Give them a second coating if needed.
Once the cookie shot glasses are finished, fill them with a splash of cold milk.
Video
Notes
Use mini chocolate chips or finely chopped chocolate. Large chips don’t fit well in the mold and can cause tearing or uneven shaping.We used dark chocolate for the coating, but candy melts work too. If you're not picky, candy melts are cheaper and easier to work with.Chill the dough before baking. Cold dough holds its shape better and helps prevent it from spilling over the edges of the mold.Want to make regular cookies with this dough? Just press the dough down on the baking sheet, they won’t spread much on their own.