1. Cream the Butter and Sugars

In a large mixing bowl, add 1 cup of softened unsalted butter, 1 cup of granulated sugar, and 1 cup of golden brown sugar. Using an electric hand mixer (or a stand mixer if you have one), cream the ingredients together on medium-high speed until the mixture is light and fluffy. This usually takes about 2–3 minutes.

Tip: Creaming properly helps create soft, pillowy cookies, so don’t rush this step.

2. Add the Wet Ingredients

Crack in one whole egg and one additional egg yolk, then add 1 teaspoon of vanilla extract. Beat the mixture again until everything is well combined. The extra yolk adds richness and enhances the chewy texture.

3. Sift in the Dry Ingredients

Place a fine-mesh sieve over the bowl and sift in 2 1/4 cups of all-purpose flour, 3/4 cup of unsweetened cocoa powder, 1 teaspoon of baking soda, and 1/2 teaspoon of salt. Sifting helps prevent clumps, especially in cocoa powder, and ensures even mixing.

Mix the dough on low speed until everything is just incorporated. Do not overmix—stop once you no longer see dry patches.

4. Form the Dough Balls and Add Rolo Centers

Using a medium-sized cookie scoop or your hands, scoop out portions of dough and roll them into balls about 1 to 1.5 inches in diameter.

Press a Rolo candy into the center of each dough ball, then mold the dough around the candy to completely cover it. The candy should not be visible.

5. Roll in Sugar

Pour 1/2 cup of granulated sugar into a small bowl. Roll each filled dough ball in the sugar to coat the outside. This gives the cookies a delicate, crackled finish once baked.

6. Bake the Cookies

Line a baking sheet with parchment paper and place the dough balls about 2 inches apart to allow for spreading.

Bake in a preheated oven at 350°F (175°C) for 8 to 10 minutes. The edges should be set, but the centers will still appear slightly soft—that’s perfect.

Important: Let the cookies cool for at least 10 minutes before eating. The caramel inside will be extremely hot straight out of the oven.