Caramel Filled Chocolate Sugar Cookies Recipe

PinExt Caramel Filled Chocolate Sugar Cookies Recipe

Ooey-gooey caramel-filled chocolate sugar cookies will knock your socks off! Crispy on the outside, gooey on the inside.

caramel filled chocolate sugar cookies 1 Caramel Filled Chocolate Sugar Cookies Recipe

Where do I start with these cookies… Because trying to find one word that would described them would be absolutely pointless. They look amazing, I am sure you’ll agree. But I wish I could poof a plateful of them right onto your tables right now. Because if you think they look tempting, just wait until you take a bite!

It’s like the world stops and you are suddenly on a long slide made out of chocolate, landing in a huge pool of gooey caramel.

caramel filled chocolate sugar cookies 2 Caramel Filled Chocolate Sugar Cookies Recipe

These cookies have a sugar-coated crispy shell and warm and gooey center that melts in your mouth. You want to take a big bite to get to the caramel filling because these babies are huge! My cookies are usually 3/4 of the size of these. I could fit only 6 on my baking sheet. They will leave you speechless the moment you take them out of the oven. Chocolatey gorgeousnsess!!  (yes, there is such a thing)

They are ridiculously easy to make! They are stuffed with Rolo candies (high five to all Rolos fans!!!) which adds even more chocolate to the center and makes the caramel melt into ooey gooey deliciousness! It will make you weak in your knees!

caramel filled chocolate sugar cookies 3 Caramel Filled Chocolate Sugar Cookies Recipe

Nothing more to say. Well, maybe one thing: MAKE THESE ASAP!

Caramel Filled Chocolate Sugar Cookies

Prep Time: 40 minutes

Cook Time: 7 minutes

Total Time: 17 minutes

Yield: 15 to 18 cookies

caramel filled chocolate sugar cookies 1 Caramel Filled Chocolate Sugar Cookies Recipe

Ooey-gooey caramel-filled chocolate sugar cookies will knock your socks off! Crispy on the outside, gooey on the inside.


  1. 1 and 1/4 c all-purpose flour
  2. 6 Tbsp unsweetened cocoa powder
  3. 1/2 tsp baking soda
  4. 1/2 c granulated sugar
  5. 1/2 c packed light brown sugar
  6. 1/2 c (1 stick) unsalted butter, room temperature
  7. 1 tsp vanilla extract
  8. 1 large egg
  9. 15 to 18 Rolos candies, unwrapped
  10. 2 Tbsp granulated sugar (for rolling)


  1. Place butter in large mixing bowl. Beat with an electric mixer for 20 seconds. Add both sugars, egg and vanilla and mix well until everything is blended well.
  2. In another mixing bowl, sift together the dry ingredients (flour, cocoa and baking soda). Add to the wet ingredients in three additions. Mix until all of the dry ingredients are incorporated.
  3. Cover the bowl and refrigerate the dough for 30 minutes.
  4. Preheat the oven to 375 degrees F.
  5. Line a cookie sheet with a parchment paper or s silicone baking mat. Set aside.
  6. Place the 2 tablespoons of sugar in a small bowl.
  7. Scoop the cookie dough with a standard size ice cream scoop, leveling on the side of the bowl.
  8. Roll the dough in your hands into a ball. Place a Rolo candie top side down into the dough ball, push down and cover with the dough on the sides. Roll again in your hands to make a ball.
  9. Roll in sugar, place on prepared baking sheet.
  10. Repeat with the rest of the dough, placing 6 balls of dough on a sheet at a time.
  11. Bake for 7 to 9 minutes (8 minutes was the magic time for me). Cool on the sheet for 2 minutes, gently transfer onto a cooling rack.


Recipe slightly adapted from Dine and Dish blog, found via Right@Home

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  • Averie Cooks

    They look amazing! I have a dark chocolate sugar cookie and although I like it, I’d LOVE it even more with Rolos inside. Great idea! pinned!

    • CrunchyCreamySw

      Thank you for pinning, Averie!

  • Stacy | Wicked Good Kitchen

    “Chocolatey gorgeousnsess” and “weak in the knees” are good things! Your cookies look divine, Anna. Suddenly, I have a chocolate and caramel craving. Thanks for sharing!

    • CrunchyCreamySw

      That’s my favorite craving. :) Thank you, Stacy!

  • Grubarazzi

    Holy wow!

    • CrunchyCreamySw

      I know, right? :)

  • cathy pollak @ Noble Pig

    I want these with my coffee…like now. Wow, they are just beautiful!!

    • CrunchyCreamySw

      Thank you, Cathy!

  • Stephanie @ Girl Versus Dough

    Oooooooh my goodness, I need at least a dozen in my life, STAT.

    • CrunchyCreamySw

      lol Thanks, Stephanie!

  • Tracy | PeanutButter and Onion

    I am putting this on my to do list

    • CrunchyCreamySw

      Yay! Thanks, Tracy!

  • Jennie @themessybakerblog

    You are my caramel stuffed cookie hero. These look bonkers delish!

    • CrunchyCreamySw

      I love it!!! Thank you, Jennie!

  • Colette

    The sugar crystals, the chocolate cookie, the cream caramel….

    • CrunchyCreamySw

      lol I told ya they make you weak in the knees! :) Thanks, Colette!

  • Ashley – Baker by Nature

    Oh me goodness, Anna… these cookies look aaaaaamazing!!!

    • CrunchyCreamySw

      Thank you, Ashley!

  • Amanda @ Once Upon a Recipe

    Anything filled with caramel is a winner in my book! I’d like to eat about 4 of them right now with my afternoon tea!

    • CrunchyCreamySw

      I hope you will get a chance to try these cookies, Amanda! You will love them!

  • Allie|Baking a Moment

    Uh, WOW! Omg I don’t even know what to say. You’ve rendered me speechless, Anna!

    • CrunchyCreamySw

      lol My work is done then :) Thanks, Allie!

  • Annie Miller

    There couldn’t possibly be a better way to eat Rollos!

    • CrunchyCreamySw

      This one is on top of the list for sure! :) Thank you, Annie!

  • Tutti Dolci

    Yes please to cookies filled with caramel!

    • CrunchyCreamySw

      Thanks, Laura!


    Oh my! Cookies filled with rolos? Oozing with chocolate and caramel? I’m sold! I need to go buy a bag of candy right now so I can make these tonight. Thank you for sharing!

    • CrunchyCreamySw

      Yay! Let me know what you think, Monet! Thanks!

  • Kate@Diethood

    Beautiful!!! I looooove that middle photo…I’d like to inhale that entire stack at once! :-)

    • CrunchyCreamySw

      And it is so easy to do that :) Thanks, Kate!

  • Jen Laceda

    They look absolutely divine!!!! I don’t think I’ve tried a cookie like this…but this is something perfect to bring to a party and impress people! Definitely piining as a “must-try” recipe.

    • CrunchyCreamySw

      Ooo! You must try them, Jen! Thanks!

  • Nancy

    Anna, I’m getting weak in the knees just looking at your gorgeous photos! And can this chocolate slide/caramel pool be a real thing? That would be the best.slide.ever. I can’t get over how ooey, gooey and molten these cookies look inside. Heavenly!

    • CrunchyCreamySw

      It totally should be a real thing! Thank you, Nancy!

  • Georgia The Comfort of Cooking

    Holy moly do these look amazing! That caramel oozing out of the cookie… oh lordy, help me! Great recipe, Anna.

    • CrunchyCreamySw

      They do that to ya :) Thank you, Georgia!

  • Curry and Comfort

    Talk about love at first bite. Love these cookies. :)

  • Rokevena

    I’ve just finished making the dough. Is to supposed to be wet looking? Or have I done somehing wrong?

    • CrunchyCreamySw

      The dough will be sticky but should not be wet. Try refrigerating the dough to make it easier to handle. Hope this helps! Thanks, Rokevena!

  • Kim (Feed Me, Seymour)

    Oh wow… Do these look amazing. I am adding them to my Christmas cookie list immediately!

  • Jocelyn

    Good gravy, these look so decadent and amazing!! I could eat more of these than I’d like to admit!! ;)

  • Margo Sweet

    Oh Man!!! I think I will follow your advise and do them ASAP :) They look incredible!!!!