Preheat the oven to 375°F. Line two baking sheets with parchment paper.
In a large mixing bowl, add the shortening, peanut butter, brown sugar, and 1/2 cup sugar. Beat until creamy.
Add the milk and vanilla and beat until combined.
In a separate bowl, add the flour, baking soda, and salt. Whisk
Add the flour mixture to the wet mixture. Fold until combined.
Roll tablespoons of dough into the remaining 1/4 cup sugar and place on the baking sheet.
Bake for 7-9 minutes, until golden. Once you remove the cookies, press into the centers of the cookies with a 1 teaspoon measuring spoon.
Microwave the chocolate chips and coconut oil in 30 second intervals until melted.
Place a dollop of chocolate into each divot and set out or refrigerate until set. Enjoy!