Preheat the oven to 350°F. Spray a cupcake pan with nonstick cooking spray.
Divide the sugar cookie dough between the 12 cupcake wells. Start with about 3 tablespoons of dough per cup and press it into the bottom and sides to form a cup. Add a little more dough if needed.
Bake for 15–17 minutes, or until the cookie cups have puffed and are lightly browned. Let them cool completely.
While the cookie cups cool, make the chocolate topping. Heat ½ cup of the heavy cream in a small saucepan until steaming but not boiling.
Place the chocolate chips in a bowl. Pour the hot cream over them and let it sit for a couple of minutes. Stir until the chocolate is melted and smooth. Set aside.
In another saucepan, combine the caramel squares and the remaining ¼ cup heavy cream. Melt over medium heat, stirring occasionally so the caramel does not stick. Remove from the heat once smooth.
Carefully remove the cooled cookie cups from the pan. A butter knife can help loosen the edges if needed. Transfer them to a platter or clean surface.
Add about 1 tablespoon of melted caramel to each cookie cup.
Spoon the melted chocolate over the caramel, filling each cookie cup to the top.
Sprinkle a little coarse salt over each one.
Refrigerate the Twix Cookie Cups for at least 15 minutes, or until the chocolate and caramel have set.