Homemade Rolo Cookies Recipe from The Food Charlatan (2024)

The very BEST Homemade Rolo Cookies recipe! No cake mix here, my friends. I have nothing against cake mix but we can make a better cookie than that, can’t we? Yes. Yes we can. Tons of cocoa and butter make an ultra fudgy cookie with a surprise caramel center! No one can resist these!

Homemade Rolo Cookies Recipe from The Food Charlatan (1)

The other day Truman was having fun making a paper airplane zoom around the room. At one point it landed on the floor next to where I was sitting, and he said, “Mom, can you get that for me?”

I was confused. “What, like, you want me to pick it up for you?” He was standing 2 feet away. “Yeah.”

Homemade Rolo Cookies Recipe from The Food Charlatan (2)

And that’s when I exploded. “NO I CAN’T PICK IT UP FOR YOU, DO YOU NOT EVEN REMEMBER THAT I’M 9 MONTHS PREGNANT, ANYTHING THAT FALLS ON THE GROUND IS DEAD TO ME!!”

Homemade Rolo Cookies Recipe from The Food Charlatan (3)

Hi, welcome to my house these days, where I will yell at you for asking me to do small favors. Poor kid’s going to be traumatized. I actually have big fears about what my kid’s early childhood memories will be. Truman’s only 6, is his first memory going to be about his mom losing it over a paper airplane?? Noo! I’m a nice mom most of the time! Just not when I’m pregnant!

Homemade Rolo Cookies Recipe from The Food Charlatan (4)

2 weeks to go you guys, and then I will stop complaining about this nonstop. Also PS the baby countdown is the same as the Christmas countdown, so you’ve got 2 weeks left to get your shopping done! Hop to it!!

Homemade Rolo Cookies Recipe from The Food Charlatan (5)

But until then, I’m baking ALLLL the cookies. I just make a huge double batch of everything and freeze the rest for later. You’ve never seen baking like a 9 month pregnant nesting food blogger. We’ve already made Butter Pecan Cookies, Gingersnaps, Spritz (hopefully updating that post soon), Cardamoms, Chocolate Chunk Gingerbread Cookies, and these AMAZING Rolo cookies.

Homemade Rolo Cookies Recipe from The Food Charlatan (6)

How to Make Rolo Cookies

You’ve had rolo cookies before, right? Or some version of them. They are a classic! Usually you see them made with cake mix cookies (one cake mix, 1/3 cup oil, 2 eggs, as found in these Homemade Oreo Cookies.)

Homemade Rolo Cookies Recipe from The Food Charlatan (7)

(Sift your cocoa if it’s clumpy)

But the basic idea is a chocolate cookie wrapped around a rolo, rolled in sugar and baked. Today’s homemade version is 10x better than the cake mix version in my humble opinion, and only takes a few more minutes to put together. You don’t even have to chill the dough! Can we get a hallelujah!!

Homemade Rolo Cookies Recipe from The Food Charlatan (8)

Wrapping one rolo in chocolate cookie dough is good.

Homemade Rolo Cookies Recipe from The Food Charlatan (9)

Homemade Rolo Cookies Recipe from The Food Charlatan (10)

But wrapping TWO rolos in chocolate cookie dough is even BETTER. Yes please. Come on now, you didn’t visit my blog because you suddenly wanted to embrace moderation, did you? Accept it.

If you do two rolos (you should) try to use the same amount of dough as you would for one rolo. The goal is to get a higher ratio of caramel to cookie, not to have a giant cookie. When I used two rolos, I made the dough balls a little more oval shape than round, as shown in the above photo on the left. One rolo sitting on top of the other (wrapped in dough).

Homemade Rolo Cookies Recipe from The Food Charlatan (11)

You can see the dough all over my fingers in the process shots above. It’s quite sticky. You are going to think these cookies will be a disaster and bake as flat as pancakes if you don’t chill them for at least a little while. That’s what I thought. But I’m glad I tried it without chilling, just to make sure! These cookies puffed up and cracked like a dream, no chilling at all. Hooray! You can go from zero to cookies in about 30 minutes with this recipe!

Homemade Rolo Cookies Recipe from The Food Charlatan (12)

See how nice and puffy they are? This is immediately out of the oven. I sprinkled with extra sugar after baking. See note above about my lack of moderation issues.

Homemade Rolo Cookies Recipe from The Food Charlatan (13)

(How many cookies do you have to take bites out of or break in half to get all the caramely photos for this blog post? About one thousand.)

Homemade Rolo Cookies Recipe from The Food Charlatan (14)

These would be such a fun cookie to add to your Christmas plates this year! No one can resist rolo cookies!

More Christmas cookies you are going to love!

  • The Best Bakery Style Double Chocolate Chip Cookies << today’s recipe is a simplified version of this one. So classic!
  • Mexican Hot Chocolate Cookies (Chocolate Snickerdoodles) << cinnamon and chocolate forever!
  • The Softest Sugar Cookies of Your Life << for real, no lies here my friends. The. Softest.
  • The Softest Chocolate Sugar Cookies << the chocolate version. So good!
  • Chocolate Crinkle Cookies << these are so ultra fudgy!
  • Homemade Oreos with Cream Cheese Frosting << you could make these cookies and stuff a rolo in them instead of using today’s recipe. Easy peasy!
  • Buried Cherry Cookies << I have made these every year for the past 12 years at least.
  • White Chocolate Cranberry Cookies << these have coconut and oatmeal and everything you need!
  • Christmas Monster Cookies from Dinner at the Zoo
  • Christmas Pretzel Hugs from Dinner Then Dessert
  • Turtle Thumbprint Cookies from I Am Baker

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Homemade Rolo Cookies Recipe from The Food Charlatan (15)

Homemade Rolo Cookies Recipe

4.86 from 14 votes

Prep: 10 minutes mins

Cook: 10 minutes mins

Total: 20 minutes mins

Servings: 34 cookies

Homemade Rolo Cookies Recipe from The Food Charlatan (16)

The very BEST Homemade Rolo Cookies! No cake mix here, my friends. I have nothing against cake mix but we can make a better cookie than that, can't we? Yes. Yes we can. Tons of cocoa and butter make an ultra fudgy cookie with a surprise caramel center! No one can resist these!

Ingredients

  • 1 cup butter, (2 sticks)
  • 1/2 cup granulated sugar
  • 1 cup brown sugar, packed
  • 2 large eggs
  • 1 tablespoon vanilla
  • 2 cups flour, spooned and leveled
  • 1 cup cocoa, sifted
  • 1 teaspoon baking soda
  • 3/4 teaspoon kosher salt
  • 35-70 rolos*
  • granulated sugar, for rolling

Instructions

  • Preheat the oven to 350 degrees F.

  • Line a few baking sheets with parchment paper or a silicone baking mat.

  • In a large bowl or stand mixer, beat 1 cup butter until light and fluffy, 2 minutes or so, scraping the edges. If you have a mixer that is powerful enough, start with cold butter, otherwise you will have to let it soften a bit.

  • Add 1/2 cup granulated sugar and 1 cup brown sugar and beat 1 more minute, scraping bottom and sides.

  • Add 2 eggs and 1 tablespoon vanilla and beat well, scraping the edges and bottom of the bowl.

  • Add 2 cups flour (spooned and leveled!), but do not mix it yet. Add 1 cup cocoa powder (if your cocoa looks clumpy, sift it into the bowl through a strainer. You don't want chunks of cocoa in your cookies.) Don't stir yet.

  • Add 1 teaspoon baking soda and 3/4 teaspoon salt. Stir the dry ingredients together a bit with a small spoon so you don't end up with any lumps of salt or soda in your cookies. Then beat the dry ingredients into the dough, but only until just incorporated.

  • When the dough is just starting to come together and there are still streaks of flour, take a second to scrape the sides and bottom of the bowl. Finish mixing it all together but don't go overboard; over-beaten cookies turn out tough. We want nice tender cookies.

  • Unwrap one thousand Rolos. Just kidding, but it might feel like a thousand. Enlist help if you can! This recipe makes about 35 cookies give or take, so you either need 35 Rolos or 70, depending on how excessive of a person you are. Obviously I added 2 Rolos for every cookie. I promise they still taste great with only one. It's totally up to you!

  • Use a spoon to scoop about 1 and 1/2 tablespoons of dough into a ball. It should be about the size of a large walnut. Don't be alarmed that the dough is pretty sticky, I promise it bakes up great. Press either 1 or 2 Rolos into the center of the dough and then wrap the dough around it so that it is completely covered. Make sure no rolo is peeking out.

  • Add about 1/2 cup or more of granulated sugar to a bowl or plate. Roll each cookie dough ball in sugar, making sure it gets well coated.

  • Place each ball on the prepared baking sheet. I did 12 cookies per sheet, but make sure you have at least 1-2 inches in between each cookie.

  • Bake at 350 for 9-10 minutes. Do not over bake! When they are done, the edges will have cracked. The cookies should not be shiny in the middle. The edges should be firm.

  • Let cool on the pan for 5 minutes before removing to a cooling rack to cool. Be aware that the center of these cookies are approximately the temperature of molten lava for the first couple minutes.

  • Eat warm with a tall glass of milk! These are great warmed up in the microwave for 10 seconds or so on day two.

Notes

*How many Rolos you need depends on whether you want to stuff one rolo or two in each cookie. There are about 50 rolos in one 10.6 ounce package.

Make ahead instructions:

Freezer: You can freeze this dough to bake later. After step 11 (when you've stuffed the cookie and rolled it in sugar) you can store these in a ziplock for up to 2 months. You can bake straight from frozen, just bake a couple minutes longer. Alternatively, you can freeze the dough for 2 months before shaping it. Let thaw before shaping, then bake as directed.

Refrigerator: This dough will keep in the refrigerator for 2-3 days. You can either refrigerate the dough in a covered bowl all together, or shape the dough with the Rolos and then chill. Make sure they are well covered! Bake as directed.

Nutrition

Serving: 1g | Calories: 236kcal | Carbohydrates: 34g | Protein: 3g | Fat: 11g | Saturated Fat: 7g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 2g | Trans Fat: 1g | Cholesterol: 28mg | Sodium: 179mg | Potassium: 102mg | Fiber: 1g | Sugar: 26g | Vitamin A: 209IU | Vitamin C: 1mg | Calcium: 44mg | Iron: 1mg

Course: Dessert

Cuisine: American

Calories: 236

Keyword: Cookies, homemade, rolo

Did you make this? I'd love to see it!Mention @thefoodcharlatan or tag #thefoodcharlatan!

Categorized as Chocolate!, Christmas Recipes, Cookies, Dessert

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Homemade Rolo Cookies Recipe from The Food Charlatan (2024)

FAQs

How thin to roll sugar cookie dough? ›

By the time you're ready to roll, the dough will be easier to handle. Dust your countertop and rolling pin with flour to prevent the dough from sticking. Roll the dough into an even thickness, about ¼ to ½ inch.

How to make even cookies? ›

And sure, this does seem like a fun little hack to make your cookies look more uniform, or at least uniformly round. All you have to do is take the baked cookies from the oven, place a mug (or a glass) over the still warm dough, do a little swirl and voilà, perfectly round cookies.

How do you chill sugar cookie dough? ›

Transfer the dough, still between the two pieces of parchment paper, to a baking sheet. Chill in the fridge for at least two hours to allow the dough to firm up, and up to three days ahead. Proceed with the recipe as written - such as my easy sugar cookie recipe.

How do you shape cookies by hand? ›

Roll the balls of cookie dough between your palms

After you've used your scoop to form all your balls of dough, take each ball and smooth it out by rolling it between the palms of your hands. This ensures you don't end up with any craggly cookies.

What is the best thickness to roll sugar cookies? ›

With a lightly floured rolling pin, roll the dough out to about 1/4-inch thickness. Use more flour if the dough seems too sticky. The rolled-out dough can be any shape, as long as it is evenly 1/4-inch thick.

What is the best thickness for sugar cookies? ›

To ensure the wonderfully soft sugar cookies of your dreams, you want to roll the dough about ¼-inch thick. This may seem too thick when you are rolling and cutting, but it's absolutely vital.

What not to do when making cookies? ›

15 Common Cookie Baking Mistakes You Might Be Making
  1. Your cookies aren't baking evenly. ...
  2. You use eggs straight from the fridge. ...
  3. You use the wrong kind of flour. ...
  4. You measure flour the wrong way. ...
  5. You soften butter too much — or not enough. ...
  6. You use stale baking powder or baking soda. ...
  7. You overwork the dough.
Nov 4, 2020

What makes cookies fluffy and not flat? ›

Room temperature butter is just the right consistency to incorporate air when it's creamed with sugar. These trapped air pockets result in risen, fluffy cookies. If the butter is any warmer, it won't incorporate enough air and your cookies will have less rise.

What happens if you don't let sugar cookie dough chill? ›

It can depend on the type of cookie dough, but for the most part, chilling the dough makes it keep its form, and if it has butter in it, prevents the butter from melting. If you don't chill the dough, it will be much softer and not keep its shape as well, both before and during baking.

What happens if you don't chill sugar cookie dough? ›

Chilling the dough is a key step in making sugar cookies, especially when you're making cut-outs. Even if you're tight on time, make sure to get the dough in the fridge, or even the freezer, even if it's only for a little while. Skip this step, and the dough will be sticky, and much harder to work with.

Should you press down cookie dough? ›

And there are no baking police: If your recipe tells you to flatten your cookies before baking, you just go ahead and do that however you want. So long as they end up evenly flat, that is; squashing cookies haphazardly under your palm means they may bake and brown unevenly.

Should I mix cookie dough by hand? ›

Cookie dough can be mixed by hand or with an electric mixer. Take butter or margarine from refrigerator 10-15 minutes before using or cut into 1-inch pieces so it will blend more easily and evenly with other ingredients.

Why should you let cookies cool before baking more cookies? ›

Dropping cookies onto a hot baking sheet — one that just came out of the oven and hasn't had a chance to cool down — means that the butter begins melting even before the cookies go into the oven. These cookies ultimately spread out too much during baking.

What thickness should the dough be when rolled out? ›

If the dough starts to warm up and becomes too difficult to handle, place it on a cutting board or baking sheet and chill for 10 to 15 minutes. Then proceed with rolling it out. The dough should be 1/8" thick and 1" wider than the pie plate.

What is the best thickness for cutout cookies? ›

But in side-by-side taste testing of different thicknesses, we found that the sugar cookies rolled out ¼-inch thick have a better mouth feel and icing to cookie ratio. Thicker cookies tend to be even softer and need to be baked an extra minute or two longer than the ¼-inch ones.

Should sugar cookies be thick or thin? ›

Roll it too thin, and the dough will be really fragile and may easily tear or break. Roll it too thick, and you run the risk of the cookies not baking evenly or cooking all the way through. → Follow this tip: For super soft, tender sugar cookies, roll the dough to 1/4-inch thick.

What is the best thickness for cookie dough? ›

Select the thickness you want (1/4-inch for cookies, but maybe a bit thinner—like 3/16—for pie, and even thinner still for fondant or, godspeed, pasta) and position your dough in between a pair.

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