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.

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

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 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.

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

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 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.

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

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.

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

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.

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

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!

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!

Did you make this recipe?

Ingredients:

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)

Directions:

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. Place mounds on a large plate or tray, cover with plasticwrap, 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.
  8. 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.
  9. 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.
Only Eats

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71 comments on “Caramel-Stuffed Quadruple Chocolate Cookies”

  1. Oh my god, the decadence! Does anyone *not* have a weakness for caramel and chocolate? And you captured the ooziness in the center so well! Cannot wait to make these.

  2. Quadruple chocolate? Oh my! I think I am in love with these cookies, especially the chocolate and caramel. Yummy. :)

  3. Yum! These look SO good :-) I love the chocolate/caramel combination

  4. Caramel stuffed?! Yes, please! These cookies look so good!

  5. Ohhhh girl–these are pinworthy!
    I need to make something caramel in the morning now after seeing these beauts!
    Have a wonderful rest of the weekend doll.

  6. Oh mama! These look so decadent and gooey!!!! In-LOVE.

  7. I’m absolutely melting in pure delight over these decadent cookies… Quadruple chocolate already sounds heavenly to a chocoholic like me, but then you go and stuff them with melted caramel too? Genius! I need to run about 10 miles if I ever baked them because with my complete lack of self-control, I’d eat the entire batch. By myself. ;) The only thing I can imagine that would even hold a candle to these incredible Rolo-stuffed cookies would be if you put a Reese’s PB cup inside instead!

  8. I think I just drooled. These look amazing and anything stuffed with caramel is a winner for me!

  9. Thick, rich, chocolatey cookies with caramel look especially delicious today…it snowed again (though its now gone) but its gray, cold and windy. Chocolate would cheer me up. Just when I think your last bar or cookie recipe put me over the moon, you go and come up with something else!! As always, these look amazing….and if I had to choose one of your chocolate cookie variations to bake tomorrow, I’d be up til the wee hours pouring over those recipes trying to decide!

    • These are my fave choc cookie recipe ever! They’re tied with the quad fudgy choc cookies that they’re adapted from. Most of the time caramel things are always better than plain, but if I’d want a more ‘neutral’ choc cookie, make those. Otherwise, these!

  10. Who could resist a Rolo-stuffed cookie?! Love how thick these are!

  11. HOLY COW. You’re my hero, seriously.

  12. Love these cookies!

  13. The melted pools of caramel or absolutely drool worthy!

  14. Chocolate around the rolo = QUINTUPLE!!

    Caramel doesn’t get enough play in the cookie world. It needs more of a spotlight.

    • I actually thought of that 5th element but I already have a quintuple choc recipe (and for some reason it’s not popular) and I didnt want there to be any confusion about the two :)

  15. Your cookies are why I dread bikini shopping this year. I guess I need more gym time because I am not willing to give up on the cookies.

  16. Every time I drop by your blog and you’ve posted another cookie recipe I get so excited because your cookies always look to die for! I am so impressed by the fact that you found a way to sneak chocolate in these 4 ways (amazing, really!) Yummy! Pinned :)

  17. Girl your killing me!! These cookies look amazing!!

  18. I hate to make cookies for my friends and I think I will make these. Thanks!

    http://cupcakesandskirts.blogspot.co.uk
    xxx

  19. Your stacks of cookies always make me speechless. These.look.amazing.
    Pinned.

  20. Wow! These look SO amazing! I’m drooling over here! I absolutely love your flavor combinations!

  21. Yum!!! These look amazing. From all of the chocolate to the gooey caramel centers I can’t imagine a more delicious cookie! Pinned! :)

  22. These cookies look heavenly! The oozing caramel is just to die for! Unfortunately we don’t have caramel squares in my area. I need to learn how to make it myself. Will try this recipe as soon as I make my own caramels. Pinned!

  23. These cookies look sinful! In the best kind of way! My husband just discovered my secret stash of rolos for baking so now its a race to see if I can use them before he eats them all!! Thank heavens you are there for me in my time of need, Averie! ;-) Pinned…not that I need to because they are all I’m going to think about until I bake them!

  24. Hi lovely! I nominated you for the Liebster Award because I love your blog – check out my latest blog post to see what it’s all about, and pass it along to your favorites :)

    http://www.simplyhsquared.com

  25. You truly make the best cookies! These look and sound insanely good and that oozing caramel, your photographs really capture that perfectly!

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