Chocolate Caramel Thumbprint Cookies

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Rich, chocolatey thumbprint cookies filled with a soft and gooey salted caramel and topped off with a simple chocolate drizzle.

I. Love. Making. Cookies.

It’s part of why I do an annual 12 Days of Cookies, part of why I share so many cookies in my Insta feed, and part of why I can rarely put my finger on my exact favorite cookie recipe.

These chocolate caramel thumbprint cookies, though? They are quite the contender for the #1 spot (competing seriously with my chewy oatmeal raisin cookies).

Let me tell you a little about where this idea for this came from.

It came from the Girl Scouts.

GIRL SCOUT COOKIE DISAPPOINTMENT

Yes, that’s right, those cute little kiddos who sell boxes of cookies for way overpriced but you can’t help but buy them because GIRL SCOUT COOKIES and not doing so would be sacrilege. 

In 2022, they came out with a cookie called Adventurefuls (here you can see what it looks like) which was described as “indulgent brownie-inspired cookies topped with caramel flavored crème with a hint of sea salt.”

I ordered these cookies with excitement because this caramel chocolate cookie sounded right up my alley and I was excited to try a chocolate thumbprint (the thumbprints I usually make are vanilla/butter based). 

When I got them, I was so disappointed. They were crunchy, not very chocolatey, and the caramel in the center was hard. There was a chocolate drizzle on top, but it was sort of melded into the whole cookie instead of this fun texture situation on top.

In hindsight, I get it– they have to be able to package up a cookie in a box without getting caramel goo all over the place. The theory was great, but the execution wasn’t, so I decided to take matters into my own hands.

The chocolatey portion? We’re getting that with one of my very favorite baking ingredients: Dutch processed cocoa powder. And more specifically, Rodelle brand. 

My favorite brand of gourmet Dutch processed baking cocoa (and a lot of other baking ingredients) is Rodelle, as they embody exactly what it means to be “fair trade,” working directly with vanilla famers in Madagascar to source their vanilla beans and other crops for their baking products. I have been working with them since 2016 and they are my go-to for almond extract and anything vanilla.

The particular unsweetened cocoa powder I used in this chocolate caramel thumbprint cookie recipe is Rodelle’s Gourmet Baking Cocoa. You can use that link to find Rodelle products near you!

In this case, we’re using pre-made caramels you can purchase at the store. I used Werther’s soft caramels, but you can also use their chewy caramels. We’ll talk about that in a minute and there are also notes in the recipe card that will help guide you with your ingredient and amount selection.

The other ingredients for the caramel filling are simple: milk and salt. These are salted caramel cookies, after all.

Then, cream together the softened butter and sugars. To this, you’ll add some vanilla extract and just one egg yolk. These cookies have a rich and dense chocolate flavor and texture due to the elimination of the egg white. 

Once your dough is together, you’ll portion it out onto baking sheets with a cookie scoop. I always use  this #50 cookie scoop for my cookie dough, and it worked perfectly for these easy caramel thumbprint cookies. 

When your dough is portioned out, you’ll smooth out the batter by rolling each cookie dough mound into a ball with your hands.

If you’re having an issue with the teaspoon measure sticking, dip it into some additional cocoa powder. This extra cocoa powder will prevent the spoon from sticking and then absorb into the cookie dough in the oven, so don’t worry if it looks like there’s cocoa powder on the surface.

If you’re going to be chilling the cookie dough more than a couple hours, cover with foil or a kitchen towel to prevent the cookie dough from drying out.

The cookies will spread a little bit and will have flattened slightly. In fact, some of the wells may have lost their shape, but fear not! This is totally fine and normal and we have a remedy.

You likely won’t need any additional cocoa powder this time, since the cookie dough will be quite buttery, but work quickly and carefully to get the walls of those wells nice and strong again. 

Again, press gently, because you don’t want to crack the cookies. The hot cookies are pretty forgiving, so don’t overthink it. Just work through them one at a time.

Put all of your caramels into a bowl with a spout (I like to use my glass measuring cup) then add some milk starting with 2 teaspoons for now.

You’ll also add a little salt, because remember, these are salted chocolate caramel cookies. As in… Extra yum!

Remember when I said you can use any kind of soft or chewy caramel you can find? After you’ve microwaved your caramels + milk + salt, stir the mixture and decide whether or not you can pour it.

You likely will be able to, but if the mixture is still too stiff, add another ½ of a teaspoon of milk. You want the mixture to be pourable but not totally liquid. Think of the viscosity of molasses. Slow moving and gooey is what we’re going for.

Then, it’s just a matter of pouring the caramel into the wells! Sounds simple enough, right?

It is, but pour with care. Nice and slow and a little at a time. Use a measuring spoon or a tablespoon if you’re worried about the caramel moving too quickly and making a mess.

The caramel won’t completely harden, but it will stiffen and set up. That’s when you’ll want to drizzle the chocolate.

Of course, when it comes to eating, these cookies are terrific and the gooey caramel center complements that rich chocolate flavor so well. My neighbors and I enjoyed these on the driveway one afternoon and had a lot of fun seeing who could get the best caramel pull. 

Honestly, I do have to thank the Girl Scouts for giving me this idea, but I’ll take all the credit for making a copycat that is a bajillion times (accurate calculation) better than the original. I hope you’ll give these better-than-the-(Girl Scout)box cookies a try the next time you’re looking to satisfy that chocolate + caramel flavor combo!