Step 1: Prep and Make Cookie Dough

1. Preheat your oven to 350 °F (175 °C).

2. Grease two muffin tins thoroughly with cooking spray.

3. In a large mixing bowl, cream together the softened butter, 1 cup brown sugar, and ½ cup granulated sugar using a hand mixer until the mixture is light and fluffy.

4. Beat in the 2 eggs and vanilla extract until fully combined.

5. Add the flour, oats, baking powder, cinnamon, and salt. Mix only until the dry ingredients are fully blended in—avoid overmixing to keep the texture tender.

Step 2: Bake the Cookie Cups

1. Use a medium cookie scoop (or about 2 tablespoons of dough) to portion the dough into each muffin cup. Press slightly to flatten but leave some thickness.

2. Bake in the preheated oven for 18 to 20 minutes, or until the tops are golden and set (cookie texture, not doughy).

3. While cookies are still warm, use a small shot glass (sprayed with cooking spray) to press gently into the center of each cookie to form a cup shape. Do this carefully so you don’t crack the edges.

4. Let the pans rest for 10 minutes, then transfer cookie cups onto wire racks to cool completely.

Step 3: Prepare Apple Filling

1. In a medium skillet over medium‑high heat, melt about 2 tablespoons of butter.

2. Add the finely chopped apples and cook until they begin to soften (3–4 minutes).

3. In a small bowl, whisk together the remaining ¼ cup brown sugar, ¼ cup granulated sugar, cornstarch, nutmeg, and cinnamon.

4. Stir that mixture into the apples. Continue cooking, stirring occasionally, until the apples are soft, tender, and the juices have thickened into a syrupy consistency (2–3 more minutes). Remove from heat and allow to cool slightly.

Step 4: Assemble & Serve

1. Spoon the warm apple filling into each cookie cup, filling it generously.

2. Drizzle with caramel sauce.

3. Serve warm or at room temperature. If serving later, you can warm briefly before serving to regain the soft apple filling.