Quadruple Chocolate Rolo Cookies — Soft and chewy cookies made with four kinds of chocolate and stuffed with Rolo candies! Ooey, gooey, and addictive!
Chocolate Cookies … with Rolos!
This Quadruple Chocolate Pudding Cookie recipe is my favorite chocolate cookie recipe.
I couldn’t resist ‘improving’ upon it by stuffing these cookies with Rolos. Insanely good.
They’re thicker, bakery-style cookies that are bold and rich, not overly sweet, and are oozing with gooey caramel and melted chocolate.
The cookies are super soft, tender, slightly chewy, and are made for serious chocolate lovers. There’s chips, chunks, cocoa, and chocolate pudding.
The cookies are just exploding with so much chocolate in every bite. The way chocolate cookies should be.
Getting to center of the cookies with that caramel just waiting to be devoured is obviously the best part. They’re going to be a tough act to follow.
Ingredients in Chocolate Rolo Cookies
To make these chocolate pudding cookies with Rolos in the middle, you’ll need the following ingredients:
- Unsalted butter
- Light brown sugar
- Granulated sugar
- Vanilla extract
- Instant chocolate pudding mix
- Unsweetened cocoa powder
- All-purpose flour
- Baking soda
- Dark chocolate bar
- Semi-sweet chocolate chips
- Rolo candies
How to Make Rolo-Stuffed Chocolate Cookies
The caramel-stuffed cookies are easy to prepare, but you need to allow time for the dough to chill before baking it. Here are the basic steps for making the cookies:
- In a large bowl, combine the butter, sugars, egg, and vanilla, and beat until creamed and well combined.
- Add the pudding mix, cocoa, and beat on low speed until just combined.
- Add the flour, baking soda, salt, and beat on low speed until just combined.
- Add the chocolate chips, chopped chocolate, and beat on low speed until just combined.
- Using a large cookie scoop, form approximately 17 equal-sized mounds of dough.
- Roll into balls, and flatten slightly. Carefully insert 1 Rolo in the center of each dough mound. Use your fingers to seal the dough around the Rolo so it’s completely enclosed.
- Place mounds on a large plate or tray, cover with plastic wrap, and refrigerate for at least 2 hours.
- After chilling, place dough mounds on baking sheet and bake until edges have set and tops are just set.
Yes, but there’s a caveat.
Over the years I’ve stuffed Twix, Snickers, Peanut Butter Cups, and more into cookies, but caramel-stuffed cookies can be tricky. Some caramels turn rock hard after baking, cooling, and setting up, and biting into them can chip a tooth. Others leak and melt into puddles all over the baking tray.
I’ve found Rolos to be a great option because they soften and melt while baking and when you bite into a warm cookie, the caramel is soft and gooey. Yet as the cookies cool, the caramel doesn’t set up too firmly.
Because the caramel is contained within the chocolate shell, it’s insurance against leaking everywhere.
If you don’t have Rolos in your area, I recommend substituting with small caramel squares.
YES! Chill the dough so the cookies bake up thick and full.
There’s no way to achieve thick, bakery-style cookies with warm, limp dough. It has no structure and collapses in the oven so you must use chilled dough for optimal results.
The instant chocolate pudding mix helps keep the cookies softbatch-style soft, supple, and there are no substitutions.
If you’re not a fan or don’t have it in your area, you can omit it, although the results won’t taste the same. Luckily I have oodles of other chocolate cookie recipes that don’t use it and recommend one of those instead.
No, this recipe will only work with instant chocolate pudding mix.
No! The pudding mix is added to the cookie dough straight from the box, like you would any other dry ingredient.
Not if you don’t have both on hand, no.
I used both so there’s varied chocolate flavors and textures present. Chopped chocolate melts in an oozing way, whereas chocolate chips have stabilizers so they stay more intact.
However, use what you have on hand or need to use up.
Tips for Making Chocolate Rolo Cookies
- Check the packaging of your pudding mix to ensure it’s instant. You can NOT use cook and serve or sugar-free pudding mix for this recipe.
- Likewise, check that your cocoa powder is unsweetened. If it’s been sweetened, your cookies will taste sickly sweet.
- I used chopped dark chocolate and semi-sweet chocolate chips, but you may throw in whatever chocolate you have on hand.
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- 3/4 cup unsalted butter, softened (1 1/2 sticks)
- 3/4 cup light brown sugar, packed
- 1/4 cup granulated sugar
- 2 large eggs
- 2 teaspoons vanilla extract
- 1 packet instant chocolate pudding mix, about 3.7 to 3.9 ounces (not sugar-free and not ‘cook & serve’)
- 1/4 cup unsweetened natural cocoa powder
- 2 cups all-purpose flour
- 1 teaspoon baking soda
- pinch salt, optional and to taste
- 1 cup semi-sweet chocolate chips
- 5 ounces dark chocolate, chopped (I used Trader Joe’s 72% Pound Plus Bar)
- about 17 Rolo Candies, unwrapped (substitute with small caramel squares or bite-sized pieces of a favorite candy bar; results will vary)
- To the bowl of a stand mixer fitted with the paddle attachment (or large mixing bowl and electric mixer) combine the butter, sugars, egg, vanilla, and beat on medium-high speed until creamed and well combined, about 4 minutes.
- Stop, scrape down the sides of the bowl, and add the pudding mix, cocoa, and beat on low speed until just combined, about 1 minute.
- Stop, scrape down the sides of the bowl, and add the flour, baking soda, optional salt, and beat on low speed until just combined, about 1 minute.
- Stop, scrape down the sides of the bowl, and add the chocolate chips, chopped chocolate, and beat on low speed until just combined, about 30 seconds.
- Using a large cookie scoop, 1/4-cup measure, or your hands, form approximately 17 equal-sized mounds of dough. Roll into balls, and flatten slightly.
- Carefully insert 1 Rolo in the center of each dough mound. Use your fingers to seal the dough around the Rolo so it’s completely enclosed. Roll dough between palms if necessary to make smooth again and flatten slightly as necessary. Repeat candy-stuffing process with all dough mounds.
- Preheat oven to 350F, line a baking sheet with a Silpat or spray with cooking spray. Place dough mounds on baking sheet, spaced at least 2 inches apart (I bake 8 cookies per sheet) and bake for about 10 minutes, or until edges have set and tops are just set, even if slightly undercooked and glossy in the center. Don’t overbake which is easy to do with dark cookies. Cookies firm up as they cool.
- Allow cookies to cool on baking sheet for about 10 minutes before serving. I let them cool on the baking sheet and don’t use a rack.
Cookies will keep airtight at room temperature for up to 1 week or in the freezer for up to 6 months.
Alternatively, unbaked cookie dough can be stored in an airtight container in the refrigerator for up to 5 days, or in the freezer for up to 4 months, so consider baking only as many cookies as desired and save the remaining dough to be baked in the future when desired.
Amount Per Serving: Calories: 314Total Fat: 16gSaturated Fat: 10gTrans Fat: 0gUnsaturated Fat: 5gCholesterol: 45mgSodium: 132mgCarbohydrates: 40gFiber: 2gSugar: 24gProtein: 4g
More Chocolate Caramel Cookies:
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Peanut Butter and Chocolate Turtle Cookies — Soft and chewy peanut butter chocolate cookies with a Turtle in the middle and drizzled with salted caramel. So darn good!
Better-Than-Girl-Scout Samoas Cookie Bars — Resembles Samoas but BETTER!! These coconut caramel cookie bars feature an Oreo crust topped with coconut, chocolate chips, and drenched in salted caramel!!
Homemade Little Debbie Star Crunch — Caramel and butter are melted and combined with marshmallows to create a gooey sweet sauce for crispy rice cereal, which provides texture and crunch. It’s almost better than the real thing!
Caramel-Stuffed Chocolate Chip Cookie Cups — The cookies are buttery soft with squishy interiors, and a slight chewiness around the edges. The best part is finding a big buttery, rich caramel in the center!