Combine powdered sugar, cocoa powder, salt, and cinnamon in a large bowl. Add coconut oil, water, and vanilla extract. Mix until a smooth syrup forms without lumps.
Add flour and baking soda. Mix in with a spatula until completely combined. Mix a couple extra times to bring everything together.
Create a 1 inch thick disk out of the dough. Wrap it in plastic wrap and place in the fridge for 10-15 minutes.
Preheat oven to 325° F and line baking trays with parchment.
Remove dough from the fridge and lightly flour both sides of disc. Between two sheets of baking parchment, roll dough to ¼ inch thick.
Use a 2 inch round cutter to stamp out as many cookies as possible. If dough has not warmed too much, remove the excess from around the cookies and transfer them to the baking sheets with 1 inch between them. If cookies are too fragile, place the cut dough in the fridge while still on the baking parchment for 3-4 minutes before attempting to transfer the cookies.
Using a ½ inch – ¾ inch round cutter (or the wide opening of a piping nozzle), cut circles from the center of half the cookies. Use the tip of a knife to remove the excess dough.
Bring all the scraps of dough together and repeat the rolling and cutting process.
Chill cut dough in the fridge for 4-5 minutes before baking to prevent spreading.
Bake for 14-15 minutes, until dry to the touch. Allow to cool on the pan for 5 minutes before moving to a rack to cool completely.
How to Make the Caramel:
In a medium saucepan with a heavy bottom, spread sugar in an even layer.
Melt over low heat without stirring. This will take some time. You can occasionally swirl the sugar to redistribute it as parts start to melt.
Once sugar is completely melted, stir slightly with a silicon spatula or metal spoon to get final crystals distributed.
Remove from heat (but leave the burner on) and stir in coconut oil. The mixture will bubble up and spit a little bit. The oil will not completely combine at this point, just stir until everything is smooth.
Add coconut cream. Stir vigorously and return to heat. Continue stirring gently while heating until all the lumps are smooth and dissolved again. Stop stirring and continue heating until a candy or instant read thermometer reaches 250-255° F
Remove from heat and wait for bubbling to settle. Once it has stopped bubbling, add vanilla and salt, stirring until combined. Pour into a glass container and set aside to cool completely.*
Place the cut-out cookies (the top portion) on a cooling rack. Dust with powdered sugar.
Place ¾ – 1 tsp caramel on each of the complete round cookies (the bottom half). Handling gently by the edges, place a powdered cut-out on top of each caramel dollop, centering as much as possible.
Allow caramel to settle. Some dripping will occur (see note about firmer caramel if preferred).
*If you allow it to cool completely and feel that it is too liquid, you can make a second batch and boil until the temperature reaches 260-265° F for a firmer caramel.