Soft and Chewy Rolo Cookies from Sweetest Menu

Soft and Chewy Rolo Cookies - made dough July 30, 2025, modified from Sweetest Menu 

1/2 cup unsalted butter, melted and cooled slightly

1/2 cup (90 grams) brown sugar

1/4 cup (50 grams) granulated sugar

1 teaspoon vanilla extract

1 large egg

1 1/2 cups (210 grams) all-purpose flour

1/2 teaspoon baking soda

pinch of salt, optional

1/2 cup dark or milk chocolate, chopped

1 cup Rolos, roughly chopped, plus extra for garnishing tops of cookies

1. Stir together melted butter, brown sugar, granulated sugar, vanilla extract and egg until well combined.
2. Add flour, baking soda and salt, if using, and stir until soft dough forms.
3. Fold in chopped chocolate and Rolos.
4. Cover and refrigerate for at least 1 hour.
5. Portion into dough balls, cover and chill or freeze for several more hours or overnight.
6. When ready to bake, preheat oven to 350 degrees F. Line baking sheets with parchment paper and evenly space dough balls. Bake 9 - 10 minutes or until edges are set and middles no longer look raw. Remove from oven and gently press Rolo halves over tops of cookies. Let rest on baking sheets for 5-10 minutes then transfer to wire rack to cool completely.

Despite the title of these cookies, I didn't use Rolos. Instead I "stuffed" them with Sanders Milk Chocolate Sea Salt caramels that I got from Costco. I love those things. I can't eat more than one in one sitting but I love them. Which means the Costco jar lasts me a long time if I don't use them in baking.

They seemed perfect to use for these cookies as they're far superior to Rolos. I made the dough and formed flat discs of small dough balls to flatten and form around each caramel. Make sure to pinch the seams closed and roll into a ball so caramel doesn't risk leaking out during baking. The dough is a little soft so I recommend freezing them first before baking.

I liked these cookies. The cookie itself is similar to a chipless chocolate chip cookie or a brown sugar cookie and you can't go wrong with stuffing it with a milk chocolate covered caramel. It's deceptively simple but makes for a nice bite-sized treat. Don't make the cookies too big as you want the caramel square inside to be the main feature and with just enough cookie surrounding it to provide a surprise in that first bite.