Preheat your oven to 350 degrees F. Grease a regular-sized muffin tin with non-stick cooking spray and then coat the cups with a little flour. (Tap off any excess.) Set aside.
In a large mixing bowl, beat together the butter, granulated sugar, powdered sugar, and vanilla for 1 to 2 minutes until fluffy and pale. Add the flour and salt and mix until just combined. (The mixture may still be a little crumbly. Do not overmix or the dough may become tough.)
Use a cookie scoop (or a 1-tablespoon measuring spoon) to add 2 tablespoons of cookie dough to each muffin tin cup. Press the dough into the bottom and about halfway up the sides of each cup.
Bake for 14 to 16 minutes or until lightly browned around the edges.
Remove the muffin tin from the oven and immediately use the tart tamper or the bottom of a shot glass to gently press the centers of the cookies down to form a cup shape.
Let the cookies cool for about 5-10 minutes in the tin. Then remove them using a butter knife to help lift them out of the wells. Place the cookie cups on a wire rack to cool completely.
Once the cookies are cooled, add the chocolate chips to a microwave-safe bowl. Heat for 30 seconds in the microwave, then stir. Heat for another 20 seconds, then stir. If the chocolate isn’t smooth yet, continue heating for 10-15 second intervals until completely melted.
Spoon 1 tablespoon of melted chocolate into each cookie cup and top with 1 tablespoon of chopped pecans. Press down lightly on the nuts so they stick to the chocolate.
Heat the caramel bits and heavy cream in a microwave-safe bowl using the same melting method as the chocolate listed above. Then drizzle the caramel over the cookie cups. Let the caramel rest until set and then enjoy!
Notes
Adding the heavy cream to the caramels when melting helps to add a soft texture that can be drizzled but sets up as it cools.
Store leftovers in a covered container at room temperature for 5-7 days. Freeze with wax paper or parchment paper between the layers in a covered container or freezer bag for up to 3 months.