• Preheat oven to 375 degrees. Spray two 12-cup mini muffin tins with cookie spray (I like the cookie spray with flour in it) and set aside.
• In the bowl of a stand mixer fitted with a paddle attachment, cream together butter and sugar on low speed until fluffy. Stir in extracts and egg, mix well, scraping down the sides as needed.
• On low speed, mix in the flour and baking soda until just combined.
• Using a medium cookie scoop or tablespoon, scoop cookie dough into prepared baking tins. Using a teaspoon, press the mixture down into each tin, creating a cup, and pressing the dough up the sides. Make sure you don’t press all the way through to the bottom, just enough to hold the filling. It will puff up during baking, so don’t worry when you see that!
• Bake for 8-10 minutes, until cookies are starting to lightly brown. Remove from oven and use teaspoon to press the centers back down (they will puff up during baking) and allow to cool completely.

To make the filling

• Combine the chocolate chips and condensed milk in a microwave safe bowl. Heat for 1 minute, then remove, add vanilla extract, and stir. If chocolate wasn’t completely melted when you took it out of the microwave, it should melt as you stir.
• Carefully spoon about a tablespoon of the mixture into the center of each cooled cookie cup, then top with a few miniature marshmallows. The fudgy filling sets up fairly quickly, so don’t be alarmed. If you need to heat it, do so about 15 seconds at a time.
• Once all the cups are filled, use the remaining chocolate to dip the ends of your pretzels handles in before attaching them to the sides of the cookie cups. Hold them in place a few seconds to make sure they stick, then set aside to set up completely. Cookie cups can be store in an airtight container for up to a week.