I know what you’re thinking. Those kinda look like Girl Scout cookies. And while they make look oddly similar, and they may even have been inspired by my favorite cookie, the Samoa, I confess, they taste nothing like Samoas/Caramel Delites. They are, however, awesome shortbread cookies dipped in chocolate, slathered in dulce de leche, and sprinkled with shredded coconut. The cookies are made with the easiest shortbread recipe in the world, and the dulce de leche is made by double boiling sweetened, condensed milk, following this recipe.
Using a double boiler (aka heatproof bowl over pot of boiling water), cook the condensed milk over low to medium heat, stirring occasionally. Cook until the milk thickens and starts to darken. It took me about 90 minutes of cooking to get the condensed milk to the right consistency for cookies. If you’re making this ahead of time, cover and store in the fridge.
Stir sugar and flour together. Add in cold butter.
Using a pastry blender (or a fork, or whatever), blend the butter into the flour and sugar. When it reaches a crumbly consistency, pack it into a tight ball, and knead it. The recipe says “until smooth,” but I did the best I could. Shortbread dough is way crumblier and harder to keep together than, say, chocolate chip cookie dough.
Take the dough and roll it out to about 1/4″ thickness. Use a cookie cutter or knife to cut out shapes. I actually used the round, metal filter from my espresso maker for these cookies. Yeah. Transfer cookies to a parchment-lined baking sheet and bake for about 25 minutes at 320 degrees F. The cookies should be a little golden around the edges but will otherwise look the same.
Carefully melt the chocolate chips in a microwave-safe bowl. I put them for about 45 seconds, stirred, then put them back in for another 30 seconds. If your dulce de leche is in the fridge, pop it in the microwave for no more than 30 seconds, then stir. Dip the bottoms of each cookie in the melted chocolate, then place on a sheet of parchment paper.
Drop a generous spoonful of dulce de leche on top of each cookie. Give it a minute to spread out over the cookies, then sprinkle each cookie with shredded coconut. Spoon the remaining chocolate into a storage bag and snip off one corner. Pipe a few lines of chocolate over each cookie. Place the cookies in the refrigerator for about 30 minutes to let the chocolate and caramel harden.