Caramel-Stuffed Quadruple Chocolate Cookies

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Quadruple Chocolate Rolo Cookies — Soft and chewy cookies made with four kinds of chocolate and stuffed with Rolo candies! Ooey, gooey, and addictive!

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.

Caramel-Stuffed Quadruple Chocolate Cookies - Soft & chewy cookies with four kinds of chocolate and so much gooey caramel! Insanely good!

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.

Caramel-Stuffed Quadruple Chocolate Cookies - Soft & chewy cookies with four kinds of chocolate and so much gooey caramel! Insanely good!

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
  • Eggs
  • Vanilla extract
  • Instant chocolate pudding mix
  • Unsweetened cocoa powder
  • All-purpose flour
  • Baking soda
  • Salt
  • Dark chocolate bar
  • Semi-sweet chocolate chips
  • Rolo candies
Caramel-Stuffed Quadruple Chocolate Cookies - Soft & chewy cookies with four kinds of chocolate and so much gooey caramel! Insanely good!

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:

  1. In a large bowl, combine the butter, sugars, egg, and vanilla, and beat until creamed and well combined.
  2. Add the pudding mix, cocoa, and beat on low speed until just combined.
  3. Add the flour, baking soda, salt, and beat on low speed until just combined.
  4. Add the chocolate chips, chopped chocolate, and beat on low speed until just combined.
  5. Using a large cookie scoop, form approximately 17 equal-sized mounds of dough.
  6. 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.
  7. Place mounds on a large plate or tray, cover with plastic wrap, and refrigerate for at least 2 hours.
  8. After chilling, place dough mounds on baking sheet and bake until edges have set and tops are just set.
Caramel-Stuffed Quadruple Chocolate Cookies - Soft & chewy cookies with four kinds of chocolate and so much gooey caramel! Insanely good!

FAQs

Can I use a different caramel candy than rolos?

Yes, but there’s a caveat.

Over the years I’ve stuffed TwixSnickersPeanut 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.

Do I have to chill the cookie dough?

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.

Can the Pudding Mix Be Substituted?

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.

Can I Use Cook and Serve pudding?

No, this recipe will only work with instant chocolate pudding mix.

Should I prepare the pudding as instructed on the packaging?

No! The pudding mix is added to the cookie dough straight from the box, like you would any other dry ingredient.

Do I Have to Use both chopped chocolate and chocolate chips?

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.

Caramel-Stuffed Quadruple Chocolate Cookies - Soft & chewy cookies with four kinds of chocolate and so much gooey caramel! Insanely good!

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.
Caramel-Stuffed Quadruple Chocolate Cookies - Soft & chewy cookies with four kinds of chocolate and so much gooey caramel! Insanely good!

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4.67 from 3 votes

Quadruple Chocolate Rolo Cookies

By Averie Sunshine
Soft and chewy cookies made with four kinds of chocolate and stuffed with Rolo candies! Ooey, gooey, and addictive!
Prep Time: 15 minutes
Cook Time: 10 minutes
Chill Time: 2 hours
Total Time: 2 hours 25 minutes
Servings: 17
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Ingredients  

  • ¾ cup unsalted butter, softened (1 1/2 sticks)
  • ¾ cup light brown sugar, packed
  • ¼ 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’)
  • ¼ 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)

Instructions 

  • 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.
  • Place mounds on a large plate or tray, cover with plastic wrap, and refrigerate for at least 2 hours, up to 5 days. Do not bake with unchilled dough because cookies will bake thinner, flatter, and be more prone to spreading.
  • 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.

Notes

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.

Nutrition

Serving: 1, Calories: 314kcal, Carbohydrates: 40g, Protein: 4g, Fat: 16g, Saturated Fat: 10g, Polyunsaturated Fat: 5g, Cholesterol: 45mg, Sodium: 132mg, Fiber: 2g, Sugar: 24g

Nutrition information is automatically calculated, so should only be used as an approximation.

Caramel-Stuffed Quadruple Chocolate Cookies - Soft & chewy cookies with four kinds of chocolate and so much gooey caramel! Insanely good!

More Chocolate Caramel Cookies:

Chocolate Chip Turtle Cookies — The BEST chocolate chip cookies stuffed with TURTLES candies!! Soft, chewy, and buttery with caramel and chocolate!

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!

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Please note: I have only made the recipe as written, and cannot give advice or predict what will happen if you change something. If you have a question regarding changing, altering, or making substitutions to the recipe, please check out the FAQ page for more info.

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Comments

  1. These look amazing!  Im debating on what caramel to use ~ rolls or the caramel squares.   Which do you think tastes better in this cookie?  Thanks

  2. These caramel filled cookies look amazing! Thinking of making some to send to friends — are these cookies that would ship well? Thanks!

    1. It would depend on how you pack them, how many days they’ll be in transit, climates, etc. I would say they’d hold up just as well as any other cookie would if being shipped. Enjoy!

  3. If I had to choose for one thing I could have on a deserted island, and it was between taking my husband or a these cookies….let’s just say I hope the island has milk.

  4. I have these chilling in the fridge right now. When I showed the pic to my husband he practically drooled and said, “yes, please.” I am so excited for them, and I am debating about adding a touch of sea salt to a couple of them before I bake them, as I adore sea salt and caramel. Thanks for publishing this recipe!

    1. If you like salted caramel or salty-and-sweet desserts, I think they’d be great with a sprinkle of sea salt on top. Some people aren’t into it, so I try limit how much salted this or that I post, but in this recipe it would work well!

  5. You are a mad cookie genius, and that’s a good thing! A very good thing! I want to stuff my face with these cookies :) Pinned!

  6. You really are the queen of gloriously indulgent, beautiful cookies. These look divine! I adore stuffed cookies, it’s just the best kind of surprise at first bite. I will definitely make these. Gorgeous! x

  7. You know I’m not crazy about chocolate but Jason would go crazy over these! And that ooey gooey caramel shot = PERFECTION!

    1. Thank you for saying that about the caramel shot. It can be so hard, glare-ey, etc..but there were a few keepers I got :) And I can go ages without chocolate but when I have to have it, I HAVE TO have it!

  8. I can’t think of a BETTER cookie, Averie! I love the combination of caramel and chocolate cookies. Especially stuffing caramel inside chocolate cookies!! Rolos are the best for stuffing too – I love biting into the first warm cookie to get all the melty caramel inside.

    1. Thank you, Sally! I know you love caramel and working with it can be a little tricky (as you know because it can leak!) so Rolos are the perfect solution :)

  9. These are like Rolos on steriods! You are nailing the gooey, melty, finger licking recipes right now!

  10. Ooozing caramel. You got me again! I want to sprinkle on sea salt to feed my unending salted caramel addiction…

    Love the softness and the fact that they’re calling to me. So gorgeous!

  11. Oh Averie, I saw these in your instagram feed yesterday and just had to check out the recipe! They look incredible! My kids will go INSANE when I make them. :-)

    1. Thanks for following on IG and you will be a superstar mama if you make these. My daughter loved these things!

  12. Rolos are the best especially warm and melty…I love how shiny your cookies look in your photos…there is no will power for these.