For the Cookies:

1. In a medium saucepan over medium-high heat, bring cider to a boil. Continue to boil until cider starts to darken and slightly thicken and is reduced to about 1/4 cup, about 15 minutes. Let cool for 10 minutes.
2. Preheat the oven to 350°F. Line 2 baking sheets with parchment paper.
3. In a large bowl, whisk together flour, cinnamon, orange zest, baking powder, ginger, baking soda, nutmeg, salt, and cloves.
4. In a medium bowl, whisk eggs, apple butter, brown sugar, oil, granulated sugar, and vanilla. Slowly pour the reduced cider into the egg mixture while whisking until combined.
5. Add the egg mixture to the dry ingredients and stir until combined.
6. Use a medium (2-oz.) cookie scoop to scoop dough onto the prepared sheets, spacing about 1″ apart.
7. Bake cookies until they are springy to the touch, about 12 to 14 minutes. Transfer them to a wire rack to cool.
8. Lightly brush the tops of cookies with melted butter and sprinkle with cinnamon sugar.

For the Filling:

1. In a large bowl, using a handheld mixer on medium-high speed, beat cream cheese and butter until light and fluffy, about 3 minutes.
2. Add confectioners’ sugar and vanilla and beat until fluffy and smooth, about 2 minutes more.
3. Scrape the filling into a pastry bag or resealable bag.

Assembly:

1. Turn cookies rounded side down. Cut the bottom of the pastry bag or the corner of the resealable bag to create a 1/2″ opening.
2. Pipe the filling into the center of half of the cookies.
3. Dollop caramel onto the center of the remaining cookies. Sandwich them together and gently press until the filling spreads almost to the edges of the cookies.
4. Cover and refrigerate whoopie pies for at least 1 hour.