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!

Yields 15 to 18 cookies

Caramel Filled Chocolate Sugar Cookies

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

40 minPrep Time

7 minCook Time

17 minTotal Time

plus Caramel Filled Chocolate Sugar Cookies Recipe Save Recipe


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


  1. Margo Sweet says

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

  2. Jocelyn says

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

  3. Kim (Feed Me, Seymour) says

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

  4. Rokevena says

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

    • CrunchyCreamySw says

      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!

  5. Nancy says

    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!

  6. says

    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.

  7. says

    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!

  8. Amanda @ Once Upon a Recipe says

    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!

  9. Stacy | Wicked Good Kitchen says

    “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!