Sea Salt Rolo Stuffed Cookies

I am truly obsessed with these sea salt Rolo stuffed cookies; I’ve made them a number of times. This recipe yields soft, chewy chocolate chip cookies with a wonderful melty caramel center. Chocolate chips pressed into the dough before baking make the cookies look delectable. And the sprinkle of sea salt on top really elevates them to new heights.

These Rolo stuffed cookies are perfect for pretty much any occasion – birthdays, potlucks, or just because. And I can attest to the extreme popularity of these salted caramel chocolate chip cookies; people have raved about them. But just be warned: they are extremely addictive. Bet you can’t have just one!

A printable version of the recipe is available below, but here’s a walkthrough of the steps to make these delicious, chewy sea salt Rolo stuffed cookies…

Important note: You’ll want the dough to get cold before forming into cookies – I recommend a minimum of 4 hours in the refrigerator, so plan accordingly. I often make the cookie batter a day in advance before baking the cookies so the dough is properly chilled.

Prepare the cookie dough

Take out two large eggs and bringing them to room temperature. You can also place them in warm water (not hot, you don’t want them to cook!) for about 6-8 minutes.

Melt butter either in the microwave (for about 30-40 seconds) or in a small saucepan over medium-low heat.

Meanwhile, in a medium/large bowl, mix together 2 and 1/3 cups of flour, 1 teaspoon baking soda, 2 teaspoons cornstarch and ½ teaspoon salt. (Note: the best way to measure flour is to spoon the flour into a measuring cup and then level it off, versus scooping with the measuring cup.)

Then in a separate smaller bowl, toss together the ¾ cup brown sugar and ½ cup white sugar. Drizzle in the melted butter and whisk well until the mixture is of a smooth consistency and no lumps remain. Whisk in both eggs, one at a time. Add in two teaspoons of pure vanilla extract and whisk until well incorporated.

Working in batches, transfer the sugar-butter-egg (wet) mixture into the dry ingredients and mix well using a rubber spatula. The dough will be fairly soft.

Mix in about half a cup of semi-sweet chocolate chips. Cover the bowl with plastic wrap and place in the refrigerator for minimum 4 hours, or up to 2 days. If you’re going to keep the dough for longer, I recommend freezing it instead (per note below). Chilling the dough is crucial to make these cookies work. I typically recommend keeping in the fridge overnight for best results.

Note: At this stage, you can freeze the cookie dough. I recommend rolling into small balls (per steps below), and then freezing separately on a cookie sheet for about 20 minutes. You can then transfer the little dough balls into a freezer Ziploc bag; these will keep for about 3-4 months. When ready to use, simply remove the dough from the freezer, let sit at room temperature for about 15-20 minutes until softened and follow steps below.

Forming the Rolo stuffed cookies

Remove the dough from the refrigerator and let warm up slightly at room temperature for 8-10 minutes.

Preheat the oven to 325F degrees.

Line two or three large baking sheets with parchment paper or silicone baking mats. I typically use three because I make my cookies smaller (more to share!).

Unwrap 23-28 Rolos (depending on how big you want your cookies) and place in a bowl. In separate bowl, prepare about 1 cups of semi-sweet chocolate chips.

Using a cookie scoop, take about 1 tablespoon of dough. Sometimes, if I want more cookies, I’ll make them slightly smaller. Roll it into a ball using your hands and place on clean cutting board or parchment paper. I usually end up with around 46-56 small dough balls.

Gently press a Rolo into one piece of dough. Cover with another piece and wrap the dough around the Rolo so there are no gaps and the candy is completely covered. Add a small sprinkle of sea salt on top. Then gently press in a few chocolate chips on top. I’ll usually go with 4-6 chocolate chips to really amp up these cookies. Repeat with the other pieces of dough.

Place the prepare Rolo stuffed cookie dough mounds on the prepared baking sheets, about 1-1.5 inches apart. I usually fit up to 11 cookies per sheet.

Baking and storing the sea salt Rolo stuffed cookies

Bake one sheet at a time in the oven for about 9-10 minutes. Place the other cookie sheets in the refrigerator or freezer as one bakes.

Remove the sheet from the oven even if the cookies look slightly underbaked – I prefer them this way. But if they bake too long, you’ll notice the cookies will start to burst and the caramel center will start to leak out.

Let the cookies cool on the cookie sheets for at least 15 minutes. Gently use a spatula to transfer the cookies to a wire rack, being sure to not rip the bottom.

These sea salt rolo stuffed cookies can be kept in an air-tight container for up to 1 week.

You can also freeze them once completely cooled. When you’re ready to eat them, take them out of the freezer and allow them to defrost at room temperature for about an hour to remove condensation. Then bake at 275°F for about 10-12 minutes, or until warm.

(for full disclaimer, this recipe was adapted from Sally’s Baking Addiction, with slight modifications.)