To make the caramel popcorn:
Preheat oven to 250°F. Line a sheet pan with parchment paper or a silicone baking mat.
Put the popcorn in a large bowl.
In a medium saucepan over medium low heat, melt the butter and sugar together. Once melting, increase the heat to medium and bring mixture to a boil, stirring constantly. Cook for 3-4 minutes, while continuing to stir.
Remove from heat and add vanilla, salt and baking soda. Stir until smooth. Immediately poor caramel over the popcorn and stir so that the popcorn is covered evenly.
Spread the caramel popcorn onto the prepared sheet pan and bake for 1 hour, stirring every 15 minutes. Let cool completely.
To make the cookies:
Preheat oven to 375°F. Line a sheet pan with parchment paper or a silicone baking mat.
In the bowl of a stand mixer fitted with a paddle attachment, beat the butter and sugars together until pale and creamy. Add the egg, followed by the vanilla, mixing after each.
In a bowl, combine the flour and baking soda. Add to the mixer and mix until combined. Add the chocolate chips and caramel popcorn and gently mix in.
Drop into rounds onto the prepared sheet pans and bake until golden, about 10-12 minutes. Let cool on the sheet pan for 5 minutes, then transfer to a cooling rack to cool completely.
Cookie recipe adapted from The Smitten Kitchen Cookbook.
Calories: 218kcal, Carbohydrates: 25g, Protein: 1g, Fat: 13g, Saturated Fat: 8g, Cholesterol: 33mg, Sodium: 91mg, Potassium: 72mg, Fiber: 1g, Sugar: 19g, Vitamin A: 309IU, Calcium: 21mg, Iron: 1mg