Preheat oven to 350 degrees Fahrenheit. Spray a regular-sized muffin pan with baking spray or grease with butter. Set aside.
In a large mixing bowl, cream butter, granulated sugar, powered sugar, and vanilla extract together for approximately 1- 2 minutes.
Add in the all-purpose flour and mix just until combined. The mixture may still be a little crumbly. Do not over mix or the dough may become tough. You can further mix with a spatula or your hands if necessary.
Using a cookie scoop or a tablespoon, add about 2 Tablespoons of dough to each muffin tin well. Press into the bottom and about halfway up the sides. Bake for 14-16 minutes or until lightly browned.
Immediately after baking, LIGHTLY and SLOWLY press the centers of the cookies down. A tart shaper, the bottom of a spice jar, or a shot glass can be used to do this. This creates a small indentation for the chocolate filling.
Let the cookies cool for about 5-10 minutes in the tin, and then carefully remove them by using a butter knife to help lift them out of the wells. Transfer to a cooling rack to finish cooling.
In a microwave-safe bowl, heat the chocolate chips or melting wafers for 30 seconds, then stir. Return to the microwave for 20 seconds, then stir. If the chocolate isn’t smooth, continue heating for 10-15 second intervals until completely melted.
Spoon about 1 Tablespoon of melted chocolate into each cookie cup and top with about 1 Tablespoon of the chopped pecans. Press down lightly on the nuts so they stick to the chocolate.
Add caramel bits and heavy cream to microwave-safe bowl. Heat them using the same melting method as the chocolate chips from above. Once completely melted drizzle the caramel over the pecans.