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!

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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!

Yield: about 17 med/large cookies

Prep Time: 15 minutes

Cook Time: 10 minutes

Total Time: 3+ hours, for dough chilling

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.

Related Recipes

Quadruple Chocolate Soft Fudgy Pudding Cookies

Quadruple Chocolate Soft Fudgy Pudding Cookies - For true chocolate lovers, these super soft cookies are loaded with chocolate!

Andes Mint Chip Soft Fudgy Chocolate Cookies - Big, thick, fudgy chocolate cookies with a hint of mint and loads of chocolate in every bite

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

Dark Chocolate Chunk and Peanut Butter Chip Chocolate Cookies - Soft and chewy cookies packed with peanut butter and oozing with dark chocolate!

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

Thick and Soft Chocolate Peanut Butter Cookies (GF) - NO butter & NO flour used in these thick cookies that taste 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

Nutella Peanut Butter Chocolate Chunk Cookies averiecooks.com

Black & White Cookies: Cream Cheese Chocolate Chip & Dark Chocolate Dark Brown Sugar - The best of both worlds in one cookie

Black & White Cookies: Cream Cheese Chocolate Chip & Dark Chocolate Dark Brown Sugar - Easy Combination Cookie Recipe at averiecooks.com

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

Soft M&M Chocolate Chip Cookies - The softest, thickest, best M&M cookies ever! People go nuts for these big cookies loaded with M&Ms and chocolate chips!

   

66 Responses to “Caramel-Stuffed Quadruple Chocolate Cookies”

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    Christy@SweetandSavoring — March 29, 2014 at 1:34 pm

    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.

    Reply

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    Chelsea @ Gal on a Mission — March 29, 2014 at 2:05 pm

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

    Reply

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    Chloe — March 29, 2014 at 2:50 pm

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

    Reply

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    Katrina @ Warm Vanilla Sugar — March 29, 2014 at 3:51 pm

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

    Reply

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    vanillasugarblog — March 29, 2014 at 4:14 pm

    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.

    Reply

    • Averie Sunshine replied: — March 30th, 2014 at 7:55 am

      Thanks for pinning and hope you’re enjoying your weekend too, sweetie! xo :)

      Reply

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    ashley - baker by nature — March 29, 2014 at 4:16 pm

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

    Reply

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    Amy @ Amy's Healthy Baking — March 29, 2014 at 4:29 pm

    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!

    Reply

    • Averie Sunshine replied: — March 30th, 2014 at 7:55 am

      There’s a reason I run a good 55-60 miles a week :)

      Reply

      • Amy @ Amy's Healthy Baking replied: — March 30th, 2014 at 1:24 pm

        Geez I’m so jealous!! My knees have been acting up and I can barely last 2. Teach me your secrets! ;)

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    Rochelle @ Oh So Sweet Baker — March 29, 2014 at 4:32 pm

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

    Reply

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    Paula — March 29, 2014 at 5:23 pm

    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!

    Reply

    • Averie Sunshine replied: — March 30th, 2014 at 7:54 am

      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!

      Reply

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    Laura (Tutti Dolci) — March 29, 2014 at 5:38 pm

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

    Reply

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    Dorothy @ Crazy for Crust — March 29, 2014 at 5:56 pm

    HOLY COW. You’re my hero, seriously.

    Reply

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    cheri — March 29, 2014 at 8:06 pm

    Love these cookies!

    Reply

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    Laura @ Laura's Culinary Adventures — March 29, 2014 at 8:18 pm

    The melted pools of caramel or absolutely drool worthy!

    Reply

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    Katie — March 29, 2014 at 9:10 pm

    Chocolate around the rolo = QUINTUPLE!!

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

    Reply

    • Averie Sunshine replied: — March 30th, 2014 at 7:50 am

      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 :)

      Reply

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    Emily @ Life on Food — March 30, 2014 at 4:02 am

    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.

    Reply

    • Averie Sunshine replied: — March 30th, 2014 at 7:49 am

      I don’t give them up either! Which is why I run daily :)

      Reply

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    Ceara @ Ceara's Kitchen — March 30, 2014 at 5:32 am

    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 :)

    Reply

    • Averie Sunshine replied: — March 30th, 2014 at 7:48 am

      Thanks for pinning and the nice compliments! :)

      Reply

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    Layla @Brunchtime Baker — March 30, 2014 at 6:31 am

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

    Reply

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    Cupcakesandskirts — March 30, 2014 at 7:57 am

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

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

    Reply

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    Anna @ Crunchy Creamy Sweet — March 30, 2014 at 8:27 am

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

    Reply

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    Gayle @ Pumpkin 'N Spice — March 30, 2014 at 9:37 am

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

    Reply

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    Jessica @ Sprinkle Some Sugar — March 30, 2014 at 11:08 am

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

    Reply

    • Averie Sunshine replied: — March 30th, 2014 at 4:32 pm

      Thanks for all your wonderful comments today! And thanks for pinning!

      Reply

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    zerrin — March 30, 2014 at 12:03 pm

    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!

    Reply

    • Averie Sunshine replied: — March 30th, 2014 at 4:31 pm

      You could just use another section of a favorite candy bar or something else you like that’s gooey!

      Reply

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    Lindsey @ American Heritage Cooking — March 30, 2014 at 12:38 pm

    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!

    Reply

    • Averie Sunshine replied: — March 30th, 2014 at 4:31 pm

      Thanks for pinning and I have more than a ‘secret stash’ of baking candy and supplies and add-ins..like a whole cupboard :)

      Reply

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    simply h squared — March 30, 2014 at 12:44 pm

    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

    Reply

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    Paula — March 30, 2014 at 3:38 pm

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

    Reply

    • Averie Sunshine replied: — March 30th, 2014 at 4:29 pm

      Thanks for the lovely compliments and I saw one of your recipes in the Ziplist newsletter 2 days ago – nice! :)

      Reply

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    Kayle (The Cooking Actress) — March 30, 2014 at 3:53 pm

    you are KILLIN me with those pictures with that oooey gooey caramel oozing out of these thick, delicious chocolate cookies!!!

    Reply

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    Jennie @themessybakerblog — March 30, 2014 at 4:01 pm

    There’s no way I can resist a chocolate cookie stuffed with a Rolo. Just…no way. Pinned.

    Reply

    • Averie Sunshine replied: — March 30th, 2014 at 4:28 pm

      And thanks for tweeting, too! And pinning :) You’re awesome!

      Reply

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    Melanie @ Carmel Moments — March 30, 2014 at 5:16 pm

    Absolutely gorgeous Averie! Wondering if I these could pass as a healthy breakfast. If so, I’d be eating good all the time. Love everything about these.

    Reply

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    marla — March 30, 2014 at 6:39 pm

    OMG! That caramel oozing out of these cookies is beyond amazing!!! Want now :)

    Reply

    • Averie Sunshine replied: — March 30th, 2014 at 6:41 pm

      I wish I could give you some!! I would love to try your latest blackberry bars recipe (so impressed with the GF factor!) and trade some cookies for that!

      Reply

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    Trish - Mom On Timeout — March 30, 2014 at 6:48 pm

    Caramel stuffed cookies are my FAVES. These look to die for Averie! Pinned!

    Reply

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    anna @ annamayeveryday — March 31, 2014 at 2:13 am

    Averie, what are those! They look beyond amazing and I am going to have to make them. Could they knock your chocolate cake off our number one spot?!

    Reply

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    pilla — March 31, 2014 at 2:18 am

    OMG! wanna eat them all right away!

    http://pernillabredolt.com

    Reply

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    lisatberry — March 31, 2014 at 2:57 am

    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.

    Reply

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    Julia @Vikalinka — March 31, 2014 at 6:53 am

    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. :-)

    Reply

    • Averie Sunshine replied: — March 31st, 2014 at 7:04 am

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

      Reply

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    Mir — March 31, 2014 at 9:10 am

    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!

    Reply

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    Mary Frances @ The Sweet {Tooth} Life — March 31, 2014 at 9:40 am

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

    Reply

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    sally @ sallys baking addiction — March 31, 2014 at 10:27 am

    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.

    Reply

    • Averie Sunshine replied: — March 31st, 2014 at 11:08 am

      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 :)

      Reply

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    Chung-Ah | Damn Delicious — April 1, 2014 at 12:52 am

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

    Reply

    • Averie Sunshine replied: — April 1st, 2014 at 12:02 pm

      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!

      Reply

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    laurasmess — April 1, 2014 at 1:12 am

    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

    Reply

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    Chichi — April 1, 2014 at 2:48 am

    Chocolate & caramel one of my fav combinations. Can’t wait to make these

    Reply

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    Jocelyn@BruCrew Life — April 3, 2014 at 10:42 pm

    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!

    Reply

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    Louanne — April 6, 2014 at 1:36 pm

    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!

    Reply

    • Averie Sunshine replied: — April 6th, 2014 at 1:50 pm

      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!

      Reply

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    Tawheda — May 25, 2014 at 4:29 am

    Wow wow wow wow!!! Thanks!

    Reply

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    Jen — July 6, 2014 at 5:16 pm

    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.

    Reply

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