Effortless to prepare yet undeniably polished, these chocolate caramel thumbprint cookies look fancy without trying and somehow manage to feel both nostalgic and just a little bit indulgent. Think tender chocolate cookie, a glossy puddle of shortcut caramel (no candy-thermometer drama, I promise) and a sparkly sprinkle of flaky sea salt. They’re nostalgic, a little flirty, and just decadent enough to feel like a special occasion (even if it’s only a rainy Tuesday afternoon).

Make a batch for gifting or keep them all for yourself. No judgment.

For make-ahead, storage, and variation tips, scroll down to the Tip Sheet after the recipe.

 

Makes 18-20 filled cookies

For the cookies:

  • 2/3 cup (4 5/8 ounces) granulated sugar, divided
  • 8 tablespoons (4 ounces) unsalted butter, softened to room temperature
  • 1/4 cup (3/4 ounces) unsweetened cocoa powder (natural or Dutch processed), sifted if lumpy
  • 1 teaspoon pure vanilla extract
  • 1/4 teaspoon table salt
  • 1 cup (4 1/2 ounces) unbleached all-purpose flour

 

For the filling & assembly:

  • 11 small caramels (3 1/8 ounces), unwrapped (I use Kraft®)
  • 1 tablespoon + 1 1/2 teaspoons heavy cream
  • Flaky sea salt

 

Make the cookies

1. Position a rack in the center of the oven and heat the oven to 350°F. Line two cookie sheets with parchment or nonstick baking liners. Put 1/3 cup (2 3/8 ounces) of the granulated sugar in a small bowl.

2. Put the butter, remaining 1/3 cup (2 3/8 ounces) sugar, cocoa powder, vanilla and salt in a large bowl of a stand mixer fitted with the paddle attachment (or in a large bowl using an electric handheld mixer fitted with wire beaters). Beat on medium speed until well blended and fluffy, about 1 minute. Add the flour and mix on low speed until well blended, about 1 minute.

3. Using a 1 tablespoon cookie scoop (I use the smallest Oxo), scoop the dough into balls and, using your palms, roll into smooth balls. Using a round 1/2-teaspoon measuring spoon, press down into the middle of each mound to make a well. If the dough sticks to the measuring spoon, dip the bottom of the spoon in a little flour. If the edges break open, reroll and try again. Carefully roll in the granulated sugar to coat the outside (don’t worry about the inside of the well) and arrange about 1 1/2 inches apart on the prepared cookie sheets.

4. Bake, one sheet at a time, until the tops look dry, 11 to 13 minutes. Move the sheet to a cooling rack and, using the same 1/2-teaspoon measuring spoon, gently press down into the center of each cookie to reform the well. Let the cookies cool for 10 minutes before moving them from the sheet to a rack to cool completely.

Make the filling and assemble

1. Put the unwrapped caramels and heavy cream in a small, heatproof bowl. Microwave in short, 15-second bursts, stirring in between, until the mixture is smooth. (This can also be done on top of the stove in a small, heatproof bowl set over simmering water, stirring until smooth.) Set aside until cool and thickened.

2. Arrange the cookies on a cookie sheet or sheet pan. Using a small spoon (I use a pointy grapefruit spoon), drizzle the thickened caramel into each well filling just to the rim. Set aside until the filling is set but still tacky to the touch. Sprinkle the tops with a little of the flaky sea salt. Cool completely before storing or serving. (See storage tips here.)

 

THE TIP SHEET

Susie Middleton

Make Ahead and Storage Tips:

  • The filled cookies can be stored at room temperature for up to two days. To keep the cookies looking their best, arrange them on a sheet pan in a single layer. Arrange four ramekins around the pan and cover the pan tightly with plastic.
  • The baked (but not filled) cookies can be stowed in an airtight container up to 5 days at room temperature or for up to 3 months in the freezer.
  • The caramel filling can be prepared and stored in the refrigerator for up to two weeks. Gently reheat in the microwave or on top of the stove and fill the cookies as directed.

 

Flavor Swaps:

Double Chocolate

2 ounces bittersweet or semisweet chocolate, chopped

3 tablespoons (1 1/2 ounces) unsalted butter, cut into 4 pieces

Melt the chocolate and butter in the microwave or in a small bowl set over simmering water, stirring until smooth. Remove from the heat and set aside until cool and slightly thickened. Top with flaky sea salt or toasted, chopped nuts.

Sprinkles or Nuts?

Sure! Instead of a dash of flaky sea salt, sub-in colored sprinkles, small candies (like mini snowcaps) or toasted, finely chopped nuts. After filling the centers with the caramel, wait a few minutes until the caramel is firm but still tacky to the touch before scattering the sprinkles or nuts on top.

Kitchen Notes

Cocoa Talk

When it comes to delivering deep chocolate flavor, I normally reach for unsweetened, natural cocoa because it delivers a strong flavor. For garnishing desserts, like truffles, I prefer Dutch-processed cocoa (it’s treated to remove the acidity), as it has a mellower, less acidic flavor. And for those times that I want to shake-up my cocoa baking game – like with these little cookies – I go all-in with black cocoa. It’s the dark, mysterious cousin of regular cocoa powder.

It’s heavily “Dutch-processed” (even more than normal) to produce a cocoa that’s strikingly black (think Oreo®-cookie black) with a flavor that’s deeper and slightly less sweet than its “natural” cousin.

Ps. Afraid to go all-in? Try pairing some of the dark cocoa with some natural cocoa. The combo gives you the best of both worlds — deep dark color paired with a more classic chocolate flavor.

Caramel Talk

The center filling is the easiest caramel ever. Seriously, no candy drama. Gently melting store-bought caramels (I use Kraft® brand) and heavy cream together makes a glossy filling with the ideal consistency – not too hard and not too runny. I always have a bag of these caramels tucked away in my pantry.

(Editor’s note: on the Island, Kraft® caramels are available at Stop & Shop.)

No microwave – no problem. I use a microwave to melt the caramels and heavy cream, but this can also be done on the stovetop. In a small saucepan, combine the caramels and heavy cream. Set the pan over very low heat and cook, stirring constantly, until the caramels have melted and the mixture is smooth, about 2 minutes. Continue as directed.

The Scoop

I use a small cookie scoop for consistently sized balls when making these cookies. I use this small cookie scoop from OXO. I then use a round ½-teaspoon measure to make a well in the dough before cooking – and right when they come out of the oven.