In a medium saucepan over medium heat, melt 2 tablespoons of unsalted butter. Add 1 teaspoon of cinnamon and stir in 6 peeled and chopped apples, ½ cup of brown sugar, 1 teaspoon of vanilla extract, 2 tablespoons of lemon juice, ½ teaspoon of nutmeg, and ½ teaspoon of kosher salt. Add 4 tablespoons of water, cover the pan, and simmer for about 5 minutes until the apples soften. Stir in 1 tablespoon of cornstarch mixed with a little water to thicken, then set aside to cool.

In a large mixing bowl, cream together 1 cup of room-temperature unsalted butter, ½ cup of brown sugar, 1 cup of granulated sugar, 1 teaspoon of cinnamon, 1 teaspoon of vanilla extract, and ½ teaspoon of kosher salt until smooth and fluffy. Beat in 2 large room-temperature eggs, one at a time, mixing well after each addition. Gradually incorporate 3 cups of all-purpose flour, 1 tablespoon of cornstarch, ⅓ teaspoon of baking soda, and ¼ teaspoon of baking powder until the dough just comes together.

Preheat your oven to 350°F (180°C) and line a baking sheet with parchment paper. Scoop about 18 tablespoon-sized balls of the cookie dough and place them on the prepared baking sheet, ensuring they are spaced apart. Use your thumb to create a deep indentation in each ball. Bake the cookies for 10 minutes, or until the edges are lightly golden. If needed, reshape the cookies gently right after taking them out of the oven for perfect edges.

Allow the cookies to cool on the baking sheet for a few minutes, then transfer them to a wire rack to cool completely. Once cooled, fill each thumbprint indentation with about 1 tablespoon of the cooled apple pie filling. Finally, drizzle with warm caramel sauce for that perfect touch of sweetness. Serve and admire your beautiful Soft Apple Pie Cookies!