Apple Crisp Cookie Cups

Preheat oven to 350°. Grease 2 muffin tins with cooking spray. In a large mixing bowl using a hand mixer, add butter, 1 cup brown sugar, and 1/2 cup granulated sugar and beat until light and fluffy. Add eggs and vanilla and mix until evenly combined. Add flour, oats, baking powder, cinnamon, and salt and stir until just combined. Using a medium cookie scoop, scoop dough into muffin tins, and press to flatten. Bake until cookie cups are golden brown and set, 18 to 20 minutes. While cookies are still warm, make the cups. Spray the bottom of a small shot glass with cooking spray and press shot glass down into center of each cookie to create cups. Let cool in pan for 10 minutes, then transfer to wire cooling racks to cool completely. Meanwhile, melt about 2 tablespoons butter in a medium skillet over medium-high heat. Add apples and cook until beginning to soften. Add remaining 1/4 cup brown sugar, 1/4 c granulated sugar, cornstarch, nutmeg, and cinnamon and cook until soft and caramelized. Spoon apple filling into cups. Drizzle with caramel and serve warm or at room temperature.