Prepare apple cider reduction by simmering 1 cup of apple cider for 10-15 minutes until reduced to ¼ cup.

Mix batter by creaming together ½ cup butter and 1 cup brown sugar until light and fluffy, then add 1 egg and 1 tsp vanilla, followed by cooled cider.

In a separate bowl, combine 1 ¾ cups flour, 1 tsp baking soda, 1 tsp baking powder, ½ tsp salt, 1 tsp each of cinnamon, nutmeg, and cloves, folding into wet ingredients alternating with ½ cup milk.

Preheat oven to 350°F (175°C) and bake mounds of dough for 10-12 minutes until golden.

While cooling, prepare filling by mixing ½ cup butter until smooth, then incorporate 2 cups powdered sugar, 2 tbsp cider, 1 tsp vanilla, and a pinch of salt.

Assemble by pairing cookies, spreading filling, drizzling caramel, and topping with another cookie.