Caramel-Stuffed Quadruple Chocolate Cookies
The Quadruple Chocolate Soft Fudgy Pudding Cookie recipe is my favorite chocolate cookie recipe.
I couldn’t resist ‘improving’ upon it by stuffing these cookies with Rolos. Insanely good.
This is actually the second adaptation of the original recipe. The first was the Andes Mint Chip Soft Fudgy Chocolate Cookies and while I do love mint and chocolate, I have a total weakness for caramel and chocolate. These are my new favorite chocolate cookie, ever.
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 recipe uses instant chocolate pudding mix. It helps keep the cookies Softbatch-style soft, supple, and there’s 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 (see Related Recipes below) that don’t use it and recommend one of those instead.
I made the dough using the Quadruple Chocolate Soft Fudgy Pudding Cookies base and stuffed each ball of dough with one Rolo. 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.
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.
There’s an abundance of melted chocolate in every bite between the chips and chunks. I use 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.
The richness of the dough, combined with the bold intense flavor of the dark chocolate chunks and semi-sweet chips, perfectly compliments the milk chocolate-coated caramels.
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
The cookies are thicker, bakery-style cookies that are bold and rich, and are oozing with melted chocolate and stuffed with Rolos. The cookies are super soft, tender, slightly chewy, and are for serious chocolate lovers. There’s chocolate chips, chunks, cocoa, and chocolate pudding mix. Pudding mix helps keep the cookies Softbatch-style soft, supple, and there’s no substitutions. You can simply omit it although the results won’t taste the same. Make sure to chill the dough so the cookies bake up thick and full. The richness of the dough, combined with the bold intense flavor of the dark chocolate chunks and semi-sweet chips, perfectly compliments the milk chocolate-coated caramels. They’re my favorite chocolate cookies!
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.
All images and content are copyright protected. Please do not use my images without prior permission. If you want to republish this recipe, please re-write the recipe in your own words, or simply link back to this post for the recipe. Thank you.
Andes Mint Chip Soft Fudgy Chocolate Cookies – Big, thick, fudgy chocolate cookies with a hint of mint and loads of chocolate in every bite
Mounds Bar Chocolate Coconut Cake Mix Cookies – Chocolate and coconut is a winning combination in these goofproof chocolate cake mix cookies that are so soft and moist
Dark Chocolate Chunk and Peanut Butter Chip Chocolate Cookies – Rich, soft chocolate cookies with chocolate chunks and peanut butter chips
Thick and Soft Chocolate Peanut Butter Cookies – Richly and intensely chocolate-flavored cookies with NO Flour, NO Butter, and NO White sugar used. They’re thick, dense, soft, chewy and like peanut butter brownies
Soft and Chewy Brownie Cookies – A soft, scrumptious, and nearly flourless brownie-like batter is baked into cookies that are rich, decadent, and lined with hidden chunks of dark chocolate
Flourless Chocolate Peanut Butter Chocolate Chip Cookies (GF) – An easy, no mixer cookie that’s naturally GF
Nutella Peanut Butter Chocolate Chunk Cookies – Nutella and peanut butter are used in the dough based, along with big chocolate chunks
Black & White Cookies: Cream Cheese Chocolate Chip & Dark Chocolate Dark Brown Sugar – The best of both worlds in one cookie
Quintuple Chocolate Fudgy Brownie Cookies – Chocolate five times: Cocoa powder, melted bittersweet baking chocolate, semi-sweet chocolate chips, diced chocolate and caramel-filled truffles, and chocolate-filled Oreos
Soft M&M Chocolate Chip Cookies – The softest, thickest, best M&M cookies ever, and made with pudding mix. Pinned over 200,000 times in 3 weeks