Rolo Stuffed Cookies Recipe

Course: cookie, Dessert

Cuisine: American

Prep Time: 15

Cook Time: 13

Chill Time: 10

Total Time: 38

Servings: cookies

Calories: 184kcal

Author: Becky Hardin

These thick and fluffy chocolate chip cookies are stuffed with a whole Rolo candy for a decadent, gooey caramel surprise in every bite.

Print Recipe

US Customary - Metric

Equipment

Kitchen Scale (optional)
2 Baking Sheet(s)
Hand Mixer
2-Tablespoon Cookie Portion Scoop

Ingredients

½ cup salted butter slightly melted (1 stick)*
¾ cup light brown sugar packed
¼ cup granulated sugar
2 large eggs room temperature
½ tablespoon pure vanilla extract
2½ cups all-purpose flour
1 teaspoon baking powder
1 teaspoon cornstarch
1½ cups semisweet chocolate chips divided
29 Rolo candies unwrapped (from 4 rolls)

Instructions

Line a large baking sheet with parchment paper and set aside.
In a large mixing bowl, using a hand mixer, cream the butter, brown sugar, and granulated sugar together until well combined, about 1-2 minutes.
½ cup salted butter, ¾ cup light brown sugar, ¼ cup granulated sugar
Beat in the eggs and vanilla until combined.
2 large eggs, ½ tablespoon pure vanilla extract
In a separate bowl, whisk the flour, baking powder, cornstarch, and salt together.
2½ cups all-purpose flour, 1 teaspoon baking powder, 1 teaspoon cornstarch
Add the dry ingredients into the wet ingredients and beat just until combined. Do not overmix.
Stir in 1¼ cups of chocolate chips, and set aside the remaining ¼ cup chocolate chips for now.
1½ cups semisweet chocolate chips
Scoop the cookies using a 2-tablespoon-sized cookie scoop. Drop scooped cookies onto the prepared baking sheet. You can place the cookies close together for now so you’ll only have one baking sheet to put into the freezer for the following step.
Press a single Rolo into the top of each cookie. Use hands to roll cookie dough around each Rolo so Rolo is completely covered. Press dough firmly into ball shapes so the dough is tight against the Rolo in the middle of the cookie. Leave cookies in round ball shape – do not flatten.
29 Rolo candies
Use remaining ¼ cup of chocolate chips to lightly press a few chocolate chips into the tops of each cookie ball.
Place the baking sheet of cookies into the freezer for 10 minutes.
While the cookies chill, preheat oven to 350°F and line a second baking sheet with parchment paper.
Place some frozen cookies on the prepared baking sheet about 2 inches apart.
Bake the cookies from frozen for 13-14 minutes. The cookies are done once the bottoms are lightly browned and the tops are set (they’ll still look soft but not raw). Let the baked cookies cool on the baking sheet for about 10 minutes before moving them onto a wire rack to cool completely.
Repeat the above steps for the remaining cookies in the freezer.

Notes

*If using unsalted butter, I recommend adding ½ teaspoon of kosher salt to the dough to balance out the sweetness.

Tips:

When wrapping the dough, make sure the seam where you closed the dough is on the top so the Rolo doesn't melt out and stick to the baking sheet.
Don't skip freezing the cookies before baking; otherwise, they will spread too much and the Rolos will leak out.
Don't freeze for longer than 15 minutes, or the Rolo won't soften before the cookie dough sets around it.
To ensure even baking time for all cookies, only bake one tray of cookies at a time.
For perfectly round cookies, as soon as the tray comes out of the oven, take a large circular glass or a round cookie cutter, place it over a hot cookie, and gently swirl it in a circular motion.

Make-Ahead: You can freeze raw cookie dough balls in an airtight container or zip-top bag for up to 3 months. I recommend freezing them until solid in a flat layer before transferring them to the container to keep them from sticking together. Bake directly from frozen, adding 1-2 minutes to the final bake time.

Storage: Store leftover Rolo candy cookies in an airtight container at room temperature for up to 1 week, or in the freezer for up to 1 month.

Nutrition