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Step 1
Prepare baking sheets by lining with parchment paper or silicone baking mats.
Step 2
With an electric mixer combine butter and sugar. Add in vanilla, baking powder and flour and mix until just combined. Take care not to overmix.
Step 3
Wrap the dough tightly in plastic wrap and chill in the fridge for an hour.
Step 4
When ready to bake, preheat oven to 350 degrees F.
Step 5
Sprinkle a bit of flour onto a clean dry counter, and roll cookie dough out to approximately 1/4″ thick. Using a round cookie cutter, cut out your cookies. Transfer cookie dough rounds to prepared baking sheet, and bake for 7-10 minutes. Take care not to overbake. You want the cookies to be set, with no glossiness on top, but not overly browned.
Step 6
Remove from oven and transfer cookie sheet to a wire cooling rack for cookies to cool.
Step 7
Prepare caramel by melting caramel bits and milk in a microwave safe bowl. Heat for one minute, then remove and carefully stir well. Remember, it’s hot and sticky! Then continue cookie, and stirring, in 20 second intervals until melted. Stir in salt.
Step 8
Place one teaspoon of caramel mixture onto each cookie. Swirl with spoon to cover the cookie if it does not spread on it’s own. Allow caramel to set up, which takes about 30 minutes. You can also place the cookies in the fridge to speed up this process.
Step 9
Combine chocolate chips and oil in a microwave safe bowl. Heat this mixture in the microwave oven at 30 seconds at a time, stirring each time. Only heat until you can stir it smooth. Do not overheat the chocolate or it can seize. Place one teaspoon of melted chocolate on top of the caramel on each cookie, giving it a swirl to cover the caramel. Once the chocolate is set, they are ready to enjoy!