9ounces(255g)soft caramels for about 1 cup melted (see note)
A tablespoon or so of cream or milk
1cup(170g)semisweet or milk chocolate for drizzling
Instructions
In a large bowl with an electric handheld mixer (or in the bowl of a stand mixer), mix the butter and sugar until light and creamy, 1-2 minutes. Add the egg yolks and vanilla and mix until combined, scraping the bowl as needed.
Add the flour and salt and mix until it comes together. Once it forms pea-size crumbs, I abandon the mixer and get in there with my hands to mush it together into a uniform ball.
Shape the soft dough into small balls. I use my #60 small cookie scoop - about 2 teaspoons of dough or .65 ounces for each cookie. Place the balls close together on a parchment-lined baking sheet. Press a small indentation in each cookie ball - don't make it too wide. I use my thumb and press down - it's ok if the sides crack a bit, just press them together. They'll look like little nests (see the picture below for a visual). Refrigerate for an hour (or longer).
Preheat the oven to 375 degrees F. Space the cookies about an inch or so apart on several parchment-lined baking sheets. They'll puff and spread just slightly but not very much. Bake for 10-11 minutes until set and lightly browned on the edges - the longer they bake (without burning, of course) the more like shortbread they'll be in texture (versus being too soft). The centers may puff up while baking, just press them back down lightly after they come out of the oven. Let the cookies cool completely.
For the caramel, if using storebought caramels, unwrap and melt the caramels with a tablespoon or so of milk or cream over low heat in the microwave or on the stovetop until creamy and smooth. Homemade caramel can usually be melted over low heat as well without the need for extra cream or milk. Dollop a bit of caramel into the center of each cooled cookie.
Let the cookies sit until the caramel cools and sets. Melt the chocolate over low heat in the microwave (or in a double boiler on the stove) and either drizzle chocolate over the cookies or spread a circle of chocolate over each caramel center. Let the chocolate set until hardened (can speed this up by refrigerating the cookies).
Notes
For the Caramels: you'll need about 1 cup of melted caramel (not caramel sauce, it needs to be soft and chewy caramels that have been melted until smooth and creamy). I used homemade - if doing so, you don't need to add the tablespoon or so of cream or milk when melting. If using storebought (like Kraft brand), use that tablespoon of cream or milk when melting the caramels. Types of Caramels: several commenters have reported back that Kraft caramels were too firm in these cookies (after melting and using them in the cookie). Others have had good success using Kraft - I think the key is not overheating the caramel when melting. Either way, you may explore other storebought options (Trader Joe's has wonderful soft caramels that may work).