Make the Cookie Dough: In a large bowl, cream the softened butter with an electric mixer on medium-high speed. Add the sugars and mix until creamed together with the butter, about 1 minute. Add the vanilla and eggs, and mix until just combined. Add the dry ingredients last, and mix until a dough forms. Chill for 30 minutes to make it easier to roll the dough into balls.

Make-Ahead Tip: Dough can be balled and frozen for 1 month or so before using. Thaw in the fridge overnight before baking.

Make the Apple Filling: Rinse & peel your apples. Dice into bite size chunks. Add all the apple filling ingredients to a medium pan over medium high heat. Cook for 15 to 18 minutes, stirring lazily the whole time. Taste around 15 minutes and finish cooking once desired tenderness is reached. Transfer apple mixture to a medium bowl to cool (this can be done at room temp or in the fridge).

Make-Ahead Tip: This can be done up to 2 days ahead. Store in a jar in the fridge.

Make the Salted Caramel Sauce: Make the Salted Caramel Sauce according to my easy, 10-minute recipe (linked in the blue text). Let cool at room temp for 20 minutes or so, until thickened.

Make-Ahead Tip: This can be cooled at room temperature and stored in a jar in the refrigerator for up to 2 weeks.

Scoop & Chill the Dough: Scoop the dough into balls 65 grams in size, with a large cookie scoop, and place in an airtight container to chill in the fridge for at least 4 hours, in the freezer for 2 hours, or in the fridge for up to 48 hours.

Note: You must scoop the dough into balls before any of these chill times. If you chill the dough solid and then scoop, it'll be very difficult, and the dough will re-warm in the process. You can chill the dough for 20 mins or so to make it a little easier to roll into balls, but then start your chill time over once the dough is balled and returned to the fridge.

Make the Crumble: Make the crumble while your dough chills. Preheat the oven to 350° F. Melt the butter in a medium mixing bowl. Stir in the remaining streusel ingredients. You should have a crumbly mixture. Crumble into small pieces on a parchment-lined pan and bake for 12-14 minutes, until deep golden brown. Set aside to cool. Break up the pieces further, as desired, while it cools, with a metal spatula.

Make-Ahead Tip: This can be made 1-2 days ahead. Store in a container at room temp, or in the freezer for 1-2 months.

Bake the Cookies: Preheat your oven to 365° F. Line a few cookie sheets with parchment paper or silicone baking mats. In a small bowl, stir together the sugar and spices for coating. Roll the dough balls in the cinnamon sugar mixture. Place about 6 cookies on each sheet, with room for them to spread.

Bake for 10-12 minutes. The edges should look and feel set when tapped with a fingertip, and the centers will be puffy and look just the tiniest bit underdone. They will set up as they cool. Let rest on the cookie sheet for 1-2 minutes, then press an indent into the centers with the back of a tablespoon. Let cool a few more minutes on the cookie sheet, then, once they feel sturdy enough, transfer to a wire rack to cool completely.

Assemble Cookies: Spoon apple pie filling into the cooled cookies, sprinkle on the crumble, and drizzle over the salted caramel sauce.

Serve & Store: Enjoy immediately once assembled! Store cookies in an airtight container in the fridge for 4-5 days. I don't recommend leaving them at room temp overnight because of the fresh fruit.