Instructions

• Make the cookie dough
• In a large bowl (or the bowl of a stand mixer), beat 3/4 cup softened butter, 1/2 cup granulated sugar, and 1/2 cup packed light brown sugar on medium speed for 2 minutes until light and fluffy. Scrape the bowl.
• Beat in 2 large eggs and 1 tsp vanilla extract on medium just until smooth and combined; scrape the bowl again.
• In a separate bowl, whisk together 2 cups flour, 1 tsp baking powder, 1 tsp cinnamon, and 1 tsp cornstarch.
• Add dry ingredients to wet in two additions, mixing on low until just combined. Don’t overmix.
• Cover and chill 30 minutes (up to overnight).
• Make the apple pie filling (while dough chills)
• Peel, core, and finely dice 2 medium apples (small dice helps them cook quickly and sit neatly on cookies).
• In a small saucepan over medium heat, melt 1 Tbsp butter. Stir in 1/4 cup packed light brown sugar and 1 tsp cinnamon until glossy and melted.
• Add apples and cook, stirring often, for 10 minutes until softened and juicy.
• Sprinkle over 2 tsp cornstarch and cook another 8–10 minutes, stirring, until thick and saucy. The mixture should coat a spoon and look jammy.
• Transfer to a shallow dish and cool to room temp, then refrigerate to speed cooling (cool filling = clean assembly).
• Bake the cookies
• Preheat oven to 375°F (190°C). Line baking sheets with parchment.
• Scoop dough into 18 equal balls (about 2 Tbsp each; a #30 scoop is perfect) and place 2 inches apart.
• Bake 12–14 minutes until edges are lightly golden and centers look just set (they’ll finish on the pan).
• Remove from oven; let sit 5 minutes. While still warm, gently press the center of each cookie with the back of a spoon to create a shallow well.
• Transfer to a rack and cool completely.
• Make the cream cheese frosting
• In a bowl, beat 8 oz cream cheese, 4 Tbsp butter, and 1 tsp vanilla on medium until smooth and fluffy, 1–2 minutes.
• Gradually beat in 2 cups powdered sugar on low, then medium, until thick, smooth, and spreadable. If too thick, beat 1–2 tsp milk; if too soft, add 1–3 Tbsp more powdered sugar.
• Assemble
• On completely cooled cookies, pipe or spoon a generous swirl of frosting.
• Top each with about 1 Tbsp cooled apple pie filling.
• Drizzle with salted caramel (warm slightly if needed so it flows in thin ribbons).
• Let the cookies sit 10–15 minutes to set, then serve!