Double Chocolate Milk and Cookie Shots

Adapted from Nicole Iizuka [1], POPSUGAR Food

For cookie shots:
Cooking spray
1 cup shortening
1/3 cup granulated sugar
1/2 cup light brown sugar
2 large egg yolks
2 teaspoons vanilla extract
2 cups all-purpose flour
1/4 cup cocoa powder
1/2 teaspoon salt
1/2 cup mini chocolate chips

For filling:
1/2 cup chocolate chips
2 tablespoons shortening
2 cups Lactaid ® 2% milk

Preheat oven to 350°F and grease shot-glass-sized baking molds with shortening.
In a large bowl, cream together shortening for 2 minutes until light and fluffy. Next add both sugars. Continue mixing for an additional 2 minutes. Then add the egg yolks and vanilla extract, and keep mixing until completely incorporated. Gradually add flour, cocoa powder, and salt. Add chocolate chips, and keep mixing until combined. The dough should be a little crumbly at this point.
Form the cookie dough inside the baking molds using your fingers to press the walls of the cookie shot to be about 1/4-inch thick. Chill for 30 minutes in the refrigerator prior to baking.
Bake for approximately 20 minutes, or until the cookies just start to brown. Remove from the oven and let cool completely.
While the cookies are cooling, melt chocolate in a microwave-safe bowl in 30-second intervals until smooth. Pour the melted chocolate into the well of each cookie, rotating to coat, and then pour the excess chocolate back into the bowl. Let some chocolate drip over the edges of the shot. Chill cookie shots until the chocolate has set.
Serve with Lactaid ® 2% milk.