Caramel-Stuffed Chocolate Chip Cookies

Adapted from Martha Stewart's Cookie Perfection

This recipe uses caramels, so feel free to use store-bought tender (not rock-hard) caramels. There are mass-market brands like Kraft and Werther's out there, but you can use what's available to you or what your preference is. Mine are salted butter caramels but you can add a few grains of salt if using unsalted caramels if you want. If your caramels aren't 1/2-ounce (12g) each, trim or press them together so that you can use that much in each cookie.

I made a few modifications to the original recipe. One was that I figured very few of us had space in our freezers for two entire baking sheets, so I advise putting the shaped cookies on something that'll fit in your freezer, such as a dinner plate or quarter sheet pan, then transfer them to baking sheets to bake them. And while they said you could bake both baking sheets at the same time, I found the cookies tend to get dark on the bottom, so baked the subsequent baking sheet on the upper third of the oven and they came out fine. If you have insulated baking sheets this is a good recipe to put them to use. (Or stack two baking sheets on top of one another.) Everyone's oven is different so check during the last 5-8 minutes of baking to make sure the bottoms of your cookies aren't getting too dark.

(Pro tip: If the bottoms of your cookies get too dark, once the cookies are cool, use a grater or Microplane-style rasp to shave any too-dark bottoms away.)

Lastly, Sarah Carey who works with Martha Stewart did a video of her making the cookies if you'd like extra guidance.

Course Dessert

Servings cookies

3 cups (420g) all-purpose flour
1 1/2 cups (270g) packed light brown sugar
1/2 cup (100g) granulated sugar
1 teaspoon baking powder
3/4 teaspoon baking soda
1 teaspoon Diamond Crystal kosher or flaky sea salt, plus additional kosher or flaky sea salt, such as Maldon or fleur de sel (optional, see headnote)
8 ounces (225g) unsalted butter, cubed and chilled
2 cups (340g) dark chocolate chips
2 large eggs , at room temperature
1 teaspoon vanilla extract
12 caramels, (about 1/2-ounce, 12g each)

In the bowl of a stand mixer fitted with the paddle attachment, mix together the flour, brown and granulated sugars, baking powder, baking soda, and salt. (You can also make the dough using a hand mixer or mix the dough by hand in a large bowl, although you may need a pastry blender, the large holes of a grater, or something similar to cut in the cold butter in the next step.)
Add the cold, cubed butter and mix on medium speed until the butter is in very small pieces, about the size of peas. Add the chocolate chips and stir until combined, then add the eggs and the vanilla and mix until the dough comes together and is smooth.
Line a dinner plate (or something similar sized that will fit in your freezer) with parchment paper or plastic film. Roll the dough into 4-ounce (115g) balls and place each on the dinner plate. If you don't have a scale, figure a generous 1/3 cup of dough per round. You should get 12 balls of dough.
Holding each piece of dough in your hand, use your thumbs to make a deep indentation in the center, deep enough to bury the caramel in. Press a caramel, flecked with a few flakes of sea salt if you wish, into the center then push the sides of the dough up over to enclose the caramel in the center. Be sure to wrap the caramel very well inside the dough, more secure than you think to avoid volcanic caramel flows in the oven. (See the picture in the post.) Place the rounds of cookie dough in the freezer for 15 minutes.
While the dough is chilling, position the oven rack in the top third of the oven and preheat to 375ºF (190ºC). Line a baking sheet with parchment paper or a silicone baking mat.
Working with one prepared baking sheet at a time, place six rounds of dough evenly spaced apart, about 3-inches (8cm), and bake the cookies for 10 minutes. Reduce the heat to 350ºF (180ºC) and rotate the baking sheet so the cookies bake evenly, then bake until the tops of the cookies are light golden brown, which will take about 7 to 8 minutes.
During the last few minutes of the recommended baking time, I suggest you check the bottoms of the cookies to make sure they're not getting too dark. At first glance, the outer edges may appear to be getting well-cooked but you can slip a spatula under a cookie to gently check the underside. In my experience, even if the edges of the bottoms appear dark, they're likely fine in the center and won't taste burnt.
When the cookies are done, remove the cookies from the oven and rap the baking sheet on the counter (which you can place a kitchen towel over if you're concerned that surface needs protection) a few times to give the cookies crackly tops, and let the cookies cool on the baking sheet set on a wire cooling rack. Once the cookies are cool, remove them from the baking sheet and bake the last six cookies the same way, making sure if using the same baking sheet that it's cooled down completely before reusing it.

Notes

Storage: The cookies will keep for up to four days in an airtight container at room temperature. The baked cookies can also be frozen for up to three months but the original notes that baking frozen cookie dough will result in "super chewy" cookies.