Preheat the oven to 350°F and line a cookie sheet or two with parchment paper.
Prepare the cookie dough according to the package directions. If using a stand mixer, start with it and finish with a spatula to combine properly.
Drop 1 1/2 tablespoon balls of dough onto the prepared cookie sheet(s). Bake for about 10 minutes. The cookies should be slightly flattened and have a hint of golden color. Note: Adjust the baking time and temperature based on the package instructions if you’re using a different surface.
Allow the cookies to cool at room temperature on the sheet or on a wire rack until they are safe to transfer. Once cooled, move them back to a cookie sheet that will fit in the fridge for the next steps in assembling.
In a small microwave-safe bowl placed over a pot of simmering water, melt the caramels and heavy cream over low heat, stirring consistently until smooth. This may take up to 10 minutes—patience is key!
Spoon a heaping tablespoon or more of caramel onto each cookie, spreading it around as needed. Refrigerate to cool. A helpful tip: work quickly as caramel can harden fast. You may find it easier to do this step on the stovetop beside the caramel.
Repeat the same melting process for the chocolate layer. Refrigerate for at least 20 minutes to let the layers cool and hold their shape.
Finally, remove from the fridge at least 10 minutes before serving to allow the caramel to soften slightly.