Preheat oven to 365℉. Line a large cookie sheet with parchment paper. Set aside. Cut 8 of the caramels in half (these are for stuffing the cookies) cut the remaining caramels in about 4 pieces (these are for topping the cookies). Set aside.
In a small bowl, stir together the flour, baking soda, salt and cinnamon. Set aside. In a medium bowl whisk together the butter, sugars, vanilla and egg until smooth. Add the flour mixture and whisk until combined and no dry flour remains. Fold in the oats and most of the chopped chocolate.
Scoop out about 16 even balls of cookie dough. Flatten and place a caramel half in the center. Fold the dough around the caramel and roll into a ball. Place 6 at a time on your prepared baking sheet, leaving plenty of room for the cookies to spread. Top each with 2-3 caramel pieces and more chocolate.
Bake for about 8 minutes. Cookies are done when the centers are puffy and the edges are set. Remove from oven and immediately top with sea salt. Let cookies set on the pan for at least 5 minutes before removing to a cooling rack. Serve warm.