Chocolate! Rolo Stuffed! Crinkle Cookies! I am so excited to share this insanely delicious cookie recipe with you from the Baker’s Royale cookbook.
These chocolate caramel filled cookies are pure decadence and pure cookie perfection.The cookies are slightly chewy, rich and chocolaty, and stuffed with a Rolo so that when you take a bite, there’s a beautiful soft caramel filling in the center.
I thought they’d be hard to make, but nope, the batter and process of making these chocolate Rolo stuffed crinkle cookies is actually quite easy.
So, confession time: I have a serious love of cookies.
You know how some people have a love of pizza and say things like “no pizza is bad pizza” even though you know that there is such a thing as bad pizza? I’m like that, but with cookies.
I love all cookies. There’s no such thing as a bad cookie. I mean yes, I’d probably take a bite of a bad cookie and think “that could have been better” but overall, I just love cookies.
Then there are those cookies that just rise above the rest. It’s memorable. When you think of “cookies” you think of that cookie.
This is one of those cookies.
Honestly, I’d say it’s top 5 cookies I’ve ever eaten, let alone made!
From the moment I tried them, I was hooked. They’re beautiful and they’re delicious. I will be making and bringing these to parties in the future, a lot.
It’s no surprise that these chocolate caramel filled crinkle cookies come from Naomi Robinson’s cookbook Baker’s Royale: 75 Twists On All Your Favorite Sweets.
Naomi is the super talented creator behind the blog BakersRoyale. Every time I’ve taken any kind of food photography workshop, when the presenter gets to the part where they talk about photography inspiration, one of Naomi’s photos are shown. And with reason! Her photography & styling is absolutely stunning. Her cookbook is full of beautiful photography and delicious sweet recipes. I’ve made several and they’re all winners.
Next time you’re need of a truly outstanding cookie, I’d highly recommend making a batch of these chocolate Rolo filled crinkle cookies!
Other recipes you might enjoy:
- 5 Ingredient Tuxedo Chip Cake Mix Cookies
- Caramel Chocolate Thumbprint Cookies Recipe
- Vanilla Bean Chocolate Chunk Cookies

Chocolate Rolo Stuffed Crinkle Cookies Recipe
Ingredients
- 1 cup 120 g all purpose flour
- 1 teaspoon baking powder
- 1/2 teaspoon instant espresso powder
- 1/4 teaspoon salt
- 6 tablespoons 86 g unsalted butter
- 2/3 60 g unsweetened cocoa powder sifted
- 1 1/2 cups 300 g light brown sugar
- 2 large eggs at room temperature
- 18 to 20 Rolos candies one per cookie
- 1/2 cup 59 g confectioners' sugar, sifted
Instructions
- Preheat the oven to 350 F. Line 2 baking sheets with parchment paper and set aside.
- In a medium bowl, whisk together the flour, baking powder, espresso powder, and salt. Set aside.
- Melt the butter in medium saucepan over medium heat or in microwave-safe bowl in 20 second increments.
- Whisk in the cocoa powder and brown sugar. Whisk in the eggs thoroughly, one at a time.
- Add the wet ingredients into the dry ingredients and mix until just combined. Scoop out 2 tablespoons of cookie dough rounds and use your hands to roll into a ball, then flatten to 1/4 inch (6mm) thick. Add a Rolo candy to the center and wrap the dough up around the candy. Roll this into an even ball, then roll it into the confectioner sugar until heavily coated. Repeat with remaining dough and candy.
- Place the cookies 2 inches apart on the prepared baking sheets. Bake in preheated oven for 8 to 10 minutes, until the cookies look crinkly and spread slightly.
- Allow the cookies to sit on the baking sheet for 5 minutes before transferring to a wire rack to cool briefly. Make sure to serve warm to get the gooey caramel.
Jennifer says
Okay so those cookies look amazing. I love chocolate cookies and I love Rolos so that’s a win/win. I’m putting them in my to make cookie list.
But, I must know the name of the polish you’re wearing in the photo. I absolutely adore it and it sets off the brown of the cookie perfectly. Did you plan that? If you did, you must teach me everything you know!
Sweetphi says
Haha, thank you so much for the comment. The nail polish is Sally Hanswen Insta Dri – “Re-Teal Therapy” lol.
I do plan the colors, thank you so much for noticing. I’ll do bright colors with blander looking things/like browns or things that need a little pop of color, and then neutral colors with things that are really colorful 🙂
Little Cooking Tips says
You had as at “espresso powder”:):):) We’ll be on the lookout for Rolos(never spotted them anywhere here before) but we’re sure we can make this work with something pretty similar:)
Thank you (and Naomi) for another amazing, DELICIOUS post dear Phi!
Love,
Mirella and Panos
xoxoxo
Sweetphi says
Thank you so much for commenting Mirella and Panos. I can’t believe there are no Rolos in Greece lol. Any chocolate covered caramels should work though. Thank you again for stopping by to comment, hope all is well with you 🙂