Preheat the oven to 325 degrees. Prepare a mini muffin tin with grease and set aside.
In a large saucepan, make the apple cider reduction. Boil the apple cider on medium/high heat until it reduces in size and turns a deep brown color. This should take about 35 to 40 min. Stir the cider occasionally. Since this takes some time, make the cookies.
Make the shortbread cookies. In a large bowl combine the melted butter, sugar, vanilla extract, and salt. Whisk to combine. Then, add the flour and mix until fully combined. The dough will be very thick.
Grab the prepared muffin tin and press down some of the batter in each cup. Fill the cups about 3/4 full and place them in the oven for about 20 minutes. The cups will be done when they have a light brown color on the sides.
While the cider is reducing and when the cookies are in the oven, gather the rest of the ingredients and prep them for use. When you start to make the caramel, it is a quick process so make sure everything is ready to go. In a small bowl, combine the cinnamon and salt. Set aside.
When the cider is ready, remove it from the heat. Then, stir in the butter, sugar, and heavy cream. Return the pot to medium heat with a candy thermometer and let the mixture come to 252 degrees. It won't take long so don't go far.
When it reaches the temp, take it off the heat and stir in the spices. Let it cool for a minute before pouring it into the measuring cup.
While the caramel cools, scoop out the middle section of the caramel cups. Don't go too far in the bottom and make sure they stay in one piece. When they are all prepared, pour the caramel in each hole and set aside to set.
While the caramel is setting, melt the chocolate. In a heatproof bowl, melt the chocolate and the coconut oil in the microwave in 15-second increments.
With the caramels set, dip the tops of the cookies into the chocolate. You want to cover the top layer so the caramel isn't visible. Set aside and allow the chocolate to harden. When the chocolate is hardened, feel free to drizzle any extra caramel on top.
If you have a lot of extra caramel, simply grease a loaf pan and pour the remaining caramel in there. Let it sit at room temperature or in the refrigerator to set. Once it is set, you can cut it into little candies.
The cookies will last about a week in an airtight container.