Pour the apple cider into a small saucepan and bring it to a gentle boil over medium-high heat. Continue cooking, stirring from time to time, until the liquid has reduced to 2 tablespoons.
Transfer the concentrated cider to a small bowl and set it aside to cool. This reduction process strengthens the apple flavor without adding excess liquid to the dough.
While the reduced cider cools, place the flour, 1 teaspoon ground cinnamon, pumpkin pie spice, baking soda, baking powder, and salt in a medium bowl.
Whisk until the ingredients are evenly distributed, then reserve the mixture for the cookie dough.
Fit a stand mixer with the paddle attachment. Add the softened butter and packed dark brown sugar to the mixer bowl, then beat until pale, light, and fluffy.
Add the egg, cooled cider reduction, and vanilla extract. Continue mixing until thoroughly incorporated.
Turn the mixer to low speed. Gradually add the prepared dry mixture and blend just until a soft, uniform dough forms.
Line a baking sheet with parchment paper or a silicone baking mat.
Combine the granulated sugar and the remaining 2 teaspoons of cinnamon in a small bowl to prepare the coating.
Using a 1½-inch cookie scoop, portion out two scoops of dough and press them together. Shape the dough into a ball, then gently flatten it into a disc.
Set one unwrapped caramel candy in the middle. Fold the dough around the candy, pinch the edges closed, and carefully roll it into a smooth ball so the caramel is completely sealed inside.
Coat the filled dough ball in the cinnamon-sugar mixture and arrange it on the lined baking sheet. Repeat until all 12 cookies have been assembled.
Place the baking sheet in the freezer for 20 minutes. Chilling firms the dough, limits excessive spreading, and helps keep the caramel enclosed.
After the chilling period, preheat the oven to 350°F (175°C).
Bake the cookies for approximately 15 minutes. They should spread slightly and develop lightly golden edges while remaining soft across the tops.
Leave the baked cookies on the baking sheet for 6–8 minutes. Carefully transfer them to a wire rack and allow them to cool completely.