Preheat your oven to 350 degrees F and spray your 2 12 count muffin tins completely with cooking spray, set aside.
In the bowl of a stand mixer with the paddle attachment, add 1 cup butter 1 cup light brown sugar and ½ cup granulated sugar.
Beat on medium speed until the butter is smooth and the sugars are fully combined, about 2 minutes.
Add the eggs and vanilla extract and beat on medium until they are combined, about 1 minute.
Then, add the rolled oats, flour, baking powder, salt and 1 teaspoon ground cinnamon. Continue beating on medium speed until all the ingredients are mixed thoroughly.
Spoon approximately 1 ½ Tablespoons of batter into each muffin cavity and lightly press to flatten.
Bake for 15-18 minutes. The edges of the cookies will be dark brown, and the middle will be a golden color.
Remove the pan from the oven. Spray the bottom of a shot glass with non-stick cooking spray and while the cookies are still hot, press the glass into the baked cookie to create a little cup. You may have to spray your glass more than once with the cooking spray to make sure that the glass doesn’t stick to the cookie.
Once you have the cups, set aside to cool for about 10-15 minutes before removing the cookies from the muffin tin to a cooling rack to cool completely.
To make the apple filling, in a small skillet, melt the remaining 2 Tablespoons butter over medium heat.
Add the apples and cook over medium heat for about 8 minutes or until the apples have softened.
Add the remaining ½ cup brown sugar, ¼ cup granulated sugar, 1 teaspoon of cinnamon, cornstarch and nutmeg to the pan and continue cooking for another 5 minutes. You want the sugars to caramelize.
Spoon 1-2 Tablespoons of the apple mixture into the cookie cups.
Drizzle the tops with caramel sauce and serve immediately.