Frosted Caramel Apple Cookies

Combine the dry ingredients. In a medium mixing bowl, whisk together the all-purpose flour, ground cinnamon, baking soda, and salt. Set aside.
Make the cookie dough. In the bowl of a stand mixer fitted with the paddle attachment, or in a large mixing bowl using an electric hand mixer, cream the butter, light brown sugar, and granulated sugar on medium speed for 2 to 3 minutes, until well combined. Add the eggs and vanilla extract and mix until smooth and combined. Add the flour mixture and mix on low speed just until the cookie dough comes together. Scrape down the sides and bottom of the bowl as needed.
Scoop and chill the dough. Using a large cookie scoop (3 tablespoons), portion the dough. Place the cookie dough balls on a parchment paper-lined baking sheet and refrigerate for 30 minutes.
Preheat the oven. While the cookie dough chills, preheat the oven to 350°F (177°C). Line baking sheets with parchment paper or silicone baking mats.
Bake the cookies. Arrange the chilled cookie dough balls on the prepared baking sheets, leaving enough space between them for spreading. Bake for 12 to 13 minutes, or until the edges are set and the centers still look slightly underbaked.
Cool the cookies. Allow the cookies to cool on the baking sheet for 2 minutes before transferring them to a wire rack to cool completely.

Whip the butter. In the bowl of a stand mixer itted with the paddle attachment, or in a large mixing bowl using an electric hand mixer, whip the room temperature butter on medium speed for 5 minutes, until light, pale, and creamy.
Add the powdered sugar. Add the powdered sugar and mix on low speed until fully incorporated, scraping down the sides and bottom of the bowl as needed.
Add the remaining ingredients. Add the salted caramel sauce, heavy cream, vanilla extract, and salt. Mix on low speed until combined, scraping down the sides and bottom of the bowl as needed.
Whip the buttercream. Increase the mixer speed to medium and whip for 2 to 3 minutes, until the buttercream is smooth and creamy.

Cook the cinnamon apples. Add the diced apples, butter, light brown sugar, and cinnamon to a large skillet. Cook over medium heat for 5 to 10 minutes, stirring occasionally, until the apples are tender but still hold their shape and the butter and brown sugar have melted together to form a thick sauce. Remove from the heat and allow the apples to cool completely.

Frost the cookies. Transfer the salted caramel buttercream to a piping bag fitted with a large round piping tip. Pipe the buttercream onto each cooled cookie, then use an offset spatula to spread the frosting, leaving a slightly raised rim around the outer edge to help contain the apples and caramel.
Add the cinnamon apples. Spoon the cooled cinnamon apple mixture into the center of each frosted cookie, keeping the apples inside the raised edge of buttercream.
Add the caramel. Transfer the salted caramel sauce to a piping bag and drizzle over the cookies. Alternatively, use a spoon to drizzle the caramel over the top. Sprinkle with flaky sea salt, if desired.

Storing & Serving

Room temperature: The assembled cookies can be kept at room temperature for up to 6 hours.
Refrigerator: Store the assembled cookies in an airtight container in the refrigerator for 3–4 days. The cinnamon apples may become a little juicy over time. Bring the cookies to room temperature before serving.
Freezer: Store baked, unfrosted cookies in an airtight freezer-safe container for up to 3 months. I don’t recommend freezing the fully assembled cookies.
Unbaked cookie dough: Store the portioned cookie dough in the refrigerator for up to 1 week or in the freezer for up to 3 months.
Salted caramel sauce: Store the salted caramel sauce in an airtight container in the refrigerator for up to 2 weeks. When ready to use, microwave in 15-second intervals until melted but still thick.

Note: Metric conversions and nutritional information are calculated automatically. I cannot guarantee the accuracy of this information.