Rolo Cookies

Featured in: Irresistible Sweet Treats

Sugar cookie mix combined with cocoa powder, wrapped around Rolo candies, chilled, then baked until the edges are set with crackly tops and melty caramel centers.

Tags: #quick-recipes #chocolate #cookies

Clare Greco
Updated on Fri, 28 Nov 2025 12:25:26 GMT
Rolo Cookies
Rolo Cookies | recipesbyclare.com
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Rolo cookies hide two chocolate-caramel candies inside each soft cocoa cookie. A sugar-cookie mix keeps the dough straightforward, while cocoa deepens the chocolate flavor and a short chill helps the candy-filled balls keep their shape.

The hands-on preparation takes about 5 minutes and baking takes 10 to 15 minutes, although the required 30-minute chill is additional. One batch makes 22 cookies. They are especially appealing served warm, when the two Rolos in every center are soft and gooey.

Rolo Cookie Ingredients

Sugar cookie mix, cocoa, butter, egg, and 48 unwrapped Rolo candies
Sugar cookie mix, cocoa, butter, egg, and 48 unwrapped Rolo candies | Recipes by Clare
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Measure one 17.5-ounce package sugar cookie mix, ¼ cup cocoa powder, ½ cup softened salted butter, and 1 egg. Unwrap 48 Rolo candies before handling the dough. Optional sanding sugar or powdered sugar can provide a decorative coating.

Softened butter should yield to gentle pressure while still holding its shape; melted butter would make the dough greasy and prone to spreading. Although the recipe makes 22 cookies with two Rolos apiece, preparing all 48 candies provides the stated amount and a small margin while shaping.

How to Make Rolo Cookies

Four stages showing cocoa dough mixed, two Rolos enclosed, chilled balls, and 22 baked cookies
Four stages showing cocoa dough mixed, two Rolos enclosed, chilled balls, and 22 baked cookies | Recipes by Clare
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  1. Line two baking sheets with parchment, but do not preheat the oven yet.
  2. Whisk the sugar-cookie mix and cocoa until the color is uniform.
  3. Beat in softened salted butter and the egg until a thick dough forms.
  4. Scoop 1½ tablespoons dough, flatten it into a disc, put exactly two Rolos in the center, and wrap the dough completely around them.
  5. Coat with sanding or powdered sugar if desired. Space balls 2 inches apart, cover, and chill at least 30 minutes.
  6. Heat the oven to 350°F. Bake 10 to 15 minutes until set and lightly cracked. Cool on the sheets at least 5 minutes, then enjoy warm.

Mix Cocoa Evenly into the Base

Whisking ¼ cup cocoa into the dry cookie mix before adding wet ingredients prevents pale streaks and concentrated bitter pockets. Break up visible cocoa lumps with the whisk. Once the mixture looks evenly chocolate colored, add the ½ cup softened salted butter and one egg.

Beat only until the mixture becomes a cohesive, thick cookie dough. Scrape the bowl so no dry mix remains at the bottom. The dough must be sturdy enough to enclose candy, so do not add milk or other liquid even if it initially appears dense.

Measure Every Portion

Use 1½ tablespoons dough for each cookie. Equal portions produce similar baking times and enough coverage for the candy center. Roll the portion briefly, flatten it into a disc, and position exactly two unwrapped Rolos together in the middle.

Bring the outer dough up and over the chocolates, then pinch the seams and roll gently until the ball is smooth. Inspect the entire surface. Any exposed caramel candy may leak against the pan when heated, so add a small patch of dough where necessary without making the cookie excessively large.

Add an Optional Sugar Finish

Before chilling, roll the shaped balls in sanding sugar for sparkle and a delicate crunch, or use powdered sugar for a snowy finish. This coating is optional and does not change the measured dough or candy filling.

Place the balls about 2 inches apart over two parchment-lined sheets. Parchment protects against sticking if a seam releases a little caramel. Keeping space around every cookie also encourages round shapes and prevents neighboring edges from merging.

Chocolate Rolo cookies with soft caramel centers
Chocolate Rolo cookies with soft caramel centers | recipesbyclare.com
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Bake Only Until Set

Wait until the chilling time is complete before heating the oven to 350°F. Transfer cold trays into the fully heated oven and bake for 10 to 15 minutes. The cookies are ready when their edges and tops appear set and the cocoa surface shows light cracks.

Do not wait for the centers to become firm in the oven. They continue cooking on the hot sheet, while the enclosed chocolate and caramel remain soft. If two pans bake together, rotate their positions only if your oven requires it for even heat.

Cool Before Moving

Leave the cookies on their baking sheets for at least 5 minutes. Fresh from the oven, the centers are molten and the bases are delicate. The resting time gives the dough structure while preserving the warm, gooey interior that defines the recipe.

Use a thin spatula to move them to a rack after that first rest. Serve warm, but allow enough time that the caramel is comfortable to eat. Store fully cooled cookies in a covered container. Brief, gentle reheating can soften the center again without rebaking the cookie.

Keep the Caramel Inside

The most reliable defense against leakage is an unbroken dough shell. Center both candies, pinch every seam, and place the smoothest side upward. The 30-minute chill then gives that shell time to firm around the filling.

If one cookie leaks, let it cool rather than trying to move hot caramel. It will still taste good, and parchment makes cleanup easier. For the remaining portions, check that no brown candy surface shows through before they enter the refrigerator.

Conclusion

Whisk a 17.5-ounce sugar-cookie mix with ¼ cup cocoa, then beat in ½ cup softened salted butter and one egg. Wrap each 1½-tablespoon portion around exactly two Rolos. Coat optionally, space 2 inches apart, cover, and chill at least 30 minutes. Bake at 350°F for 10 to 15 minutes and cool on the sheets for at least 5 minutes.

Frequently Asked Questions

→ Why are Rolo cookie balls chilled?

At least 30 minutes of chilling firms the butter and thick dough, reducing rapid spread and helping keep the caramel centers enclosed.

→ How many Rolos go in each cookie?

Place exactly two unwrapped Rolos in the center of every 1½-tablespoon dough disc before sealing it.

→ When are the cookies done?

After 10 to 15 minutes at 350°F, the surfaces should look set and lightly cracked even though the centers remain soft.

→ Can the sugar coating be omitted?

Yes. Sanding sugar or powdered sugar is an optional decorative finish; the cocoa cookie and caramel center do not depend on it.

4.60 from 40 votes

Chocolate Caramel Stuffed Cookies

Preparation Time:
5 Minutes
Cook Time:
10 Minutes
Total Cooking Time:
15 Minutes
Number of Servings:
22
Rolo Cookies
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Soft chocolate cookies made with sugar cookie mix, stuffed with two Rolos each for a gooey caramel surprise inside.

Ingredients You'll Need

  • Main Ingredients

How to Make It

1.

1. Prep Your Pans: Line two cookie sheets with parchment paper. Don't preheat the oven yet - these cookies need to chill first.

2.

2. Mix the Dry Ingredients: In a large mixing bowl, whisk together the sugar cookie mix and cocoa powder until well combined.

3.

3. Make the Dough: Using a hand mixer or stand mixer, beat in the softened butter and egg until a thick dough forms.

4.

4. Stuff with Rolos: Use a cookie scoop (about 1 1/2 tablespoons) to scoop out a large ball of dough and flatten it into a disc. Place two unwrapped Rolos in the center and gently wrap the dough around them, forming a smooth ball.

5.

5. Coat and Place: If you're using sugar, roll the ball in sanding sugar or powdered sugar to coat. Place the ball on one of your prepared cookie sheets. Repeat with the rest of the dough, spacing the cookies about 2 inches apart.

6.

6. Chill the Dough: Once all the cookies are on the sheets, cover them with plastic wrap and pop them in the fridge for at least 30 minutes. This step is important - it keeps the cookies from spreading too much.

7.

7. Preheat the Oven: A few minutes before you're ready to bake, heat your oven to 350 degrees.

8.

8. Bake the Cookies: Take the cookie sheets out of the fridge and remove the plastic wrap. Bake for 10 to 15 minutes until the edges are set and the tops start to crack a bit.

9.

9. Cool and Serve: Take the cookies out of the oven and let them cool on the baking sheet for at least 5 minutes before moving them to a cooling rack. You can also serve them warm for that gooey caramel center!

Extra Information

  1. Chilling the dough is important - it prevents the cookies from spreading too flat while baking.
  2. These cookies are best enjoyed warm when the Rolo centers are still gooey.
  3. Store in an airtight container at room temperature for up to 5 days.
  4. You can use any sugar cookie mix brand you like.

Essential Tools

  • Two cookie sheets
  • Parchment paper
  • Large mixing bowl
  • Hand mixer or stand mixer
  • Whisk
  • Cookie scoop (1 1/2 tablespoons)
  • Plastic wrap
  • Wire cooling rack

Allergy Warnings

Please check ingredients for potential allergens and consult a health professional if in doubt.
  • Contains dairy (butter, Rolos)
  • Contains eggs
  • Contains gluten (cookie mix)
  • May contain soy (cookie mix, chocolate)

Nutrition Details (Per Portion)

It is important to consider this information as approximate and not to use it as definitive health advice.
  • Calories: 177
  • Total Fat: 8 g
  • Total Carbohydrate: 26 g
  • Protein: 2 g