Preheat the oven to 375 degrees.
Prepare a large baking sheet with parchment paper.
Beat the butter at medium speed until fluffy.
Slowly add the sugar, scraping the bowl down as needed.
Add the egg yolks and vanilla, blending until well mixed.
Add the flour a little at a time and beat until combined.
Refrigerate the cookie dough for at least one hour.
Using a small (about 1 tablespoon) cookie scoop, place the cookie dough at least 1 inch apart. Bake for 10 minutes.
When the cookies are done, remove them from the oven and gently press the back of a teaspoon into the center of each cookie.
Allow the cookies to cool on the baking sheet.
Meanwhile, place the caramel bits and cream in a microwaveable bowl.
Heat in the microwave, stirring every 30 seconds until smooth.
Spoon a small amount of the caramel into the hole in each cookie.
In another microwavable bowl, place the caramel bits and cream.
Heat in the microwave, stirring every 30 seconds until smooth.
Transfer to a piping bag or zip-top storage bag with the corner snipped. Drizzle over the cookies.
Allow the chocolate to set completely before serving.