01 -  In a small skillet over medium heat, melt unsalted butter. Add diced apples, brown sugar, ground cinnamon, ground nutmeg, and a pinch of salt. Cook, stirring frequently, until apples are tender and mixture is syrupy, approximately 5 to 7 minutes. Allow to cool completely. 
 02 -  In a separate bowl, whisk together all-purpose flour, baking powder, salt, and ground cinnamon. In a large bowl, beat softened butter, granulated sugar, and light brown sugar with an electric mixer until creamy, about 2 minutes. Incorporate the egg and vanilla extract, then gradually add the flour mixture. Mix until dough just comes together. 
 03 -  Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper. Using approximately 2 tablespoons of dough per portion, flatten each into a disc. Place 1 teaspoon of cooled apple filling in the center, fold dough around the filling, and roll into a ball. Insert a lollipop stick halfway into each ball, ensuring the dough is sealed. 
 04 -  In a shallow bowl, blend remaining granulated sugar and ground cinnamon for coating. Roll each filled cookie ball in the cinnamon sugar mixture. Arrange on the prepared baking sheet, spacing each pop roughly 2 inches apart. Bake for 15 to 18 minutes, until the surface is lightly golden. Let cookies cool on the pan for 5 minutes before transferring to a wire rack. 
 05 -  Drizzle melted caramels over the cooled cookie pops. If desired, sprinkle with flaky sea salt. Allow the caramel to set fully before serving.