Chewy Chocolate Caramel Cookies

Category: Treats That Make Everything Better

Indulge in these chewy chocolate caramel cookies for a deliciously sweet dessert. Each cookie starts with a simple cocoa-kissed dough made from sugar cookie mix, softened butter, and a single egg, coming together quickly for easy preparation. Wrapped around two indulgent Rolos, the center transforms into a gooey treasure once baked. Optional sanding or powdered sugar adds a sweet sparkle on top. Chill the dough, shape, and bake for a treat featuring a crisp edge and a soft, molten caramel core. Serve warm for best results and enjoy every bite of chocolate and caramel harmony.

Lili Clark smiling at the camera.
Created By Lili Clark
Updated on Fri, 28 Nov 2025 14:11:14 GMT
Rollo cookies with peanut butter and jelly. Save
Rollo cookies with peanut butter and jelly. | lilicooks.com

These Rolo cookies have become my go-to whenever I need an easy crowd-pleasing dessert. Each bite delivers a gooey caramel center wrapped in soft chocolate cookie—a hit at every gathering with kids and grown-ups alike.

My family always argues over who gets the last one. I love how these cookies stay soft even the next day and they never last long at any of our parties.

Ingredients

  • Sugar cookie mix: Choose a good quality mix for best flavor and soft texture
  • Cocoa powder: Adding this transforms the dough into rich chocolate cookies try to use Dutch-processed for deeper color
  • Salted butter: Softened butter gives body and buttery taste using salted is key for flavor balance
  • Large egg: Helps bind and adds chewiness use the freshest eggs you have
  • Rolos: These are the star a milk chocolate shell with caramel inside always unwrap ahead to save time
  • Sanding or powdered sugar: Optional for an elegant finish and bit of sparkle thicker grains work best for crunch

Step-by-Step Instructions

Prepare the Pans:
Line two cookie sheets with parchment paper to keep cookies from sticking and speed up cleanup. No need to preheat the oven yet since dough will need to chill.
Mix the Dry Ingredients:
Combine sugar cookie mix and cocoa powder in a large mixing bowl. Mix well to distribute the cocoa evenly for consistent chocolate flavor.
Make the Dough:
Add softened butter and the egg to the bowl. Beat with a hand or stand mixer until a thick even dough forms. Scrape the sides often to catch all dry spots.
Shape the Cookies:
Scoop out dough using a one and a half tablespoon scoop for uniform cookies. Flatten each scoop into a disc to make space for the filling.
Add the Rolo Centers:
Place two unwrapped Rolos in the center of each disc. Gently wrap the dough around and roll into a smooth ball so no caramel shows.
Coat and Arrange:
Roll the dough balls in sanding or powdered sugar if you like a sparkly or snowy look. Set on lined sheets leaving space for spreading.
Chill the Dough:
Cover the trays with plastic wrap. Chill in the fridge for at least thirty minutes. This prevents the cookies from overspreading and helps set the flavor.
Preheat and Bake:
When ready to bake preheat the oven to three fifty degrees Fahrenheit. Bake chilled cookies for ten to fifteen minutes until edges firm up and tops crack.
Cool and Enjoy:
Let cookies cool on the tray at least five minutes before moving them to a cooling rack. Serve warm for gooey caramel or cool for neater bites.
Chocolate cookies with caramel filling. Save
Chocolate cookies with caramel filling. | lilicooks.com

You Must Know

  • Great for freezing store dough balls or baked cookies
  • Perfect for cookie exchanges or edible gifts
  • Easy to double for parties

The Rolos are my absolute favorite part. As a kid my mom surprised us with these just after school and to this day I still cannot resist breaking one open while the caramel is melting hot.

Storage Tips

Keep cooled cookies in an airtight container at room temperature for up to four days. For longer storage freeze baked cookies in layers separated by parchment paper. You can freeze unbaked dough rounds as well and bake them straight from frozen just add an extra minute or two in the oven.

Ingredient Substitutions

If you cannot find Rolos any caramel-filled chocolate works but the size might change bake time. You can use unsalted butter plus an extra pinch of salt if you prefer. If you want richer chocolate try mixing dark and Dutch-process cocoa powders. Gluten-free sugar cookie mix also works for allergy needs.

Rollo cookies with chocolate and caramel toppings. Save
Rollo cookies with chocolate and caramel toppings. | lilicooks.com

Serving Suggestions

Serve these Rolo cookies warm straight from the oven for melty centers or with a scoop of vanilla ice cream for an extra treat. They make great additions to holiday cookie platters or lunchbox desserts. I sometimes sprinkle a pinch of flaky salt on top for a gourmet finish.

History of This Cookie

Rolo cookies saw their big rise in American kitchens after Rolos hit the shelves in the thirties. People loved using candy as baking shortcuts and today these treats are beloved at bake sales and potlucks. Rolo cookies feel a bit retro but always deliver a wow factor.

Recipe FAQs

→ Can I use unsalted butter instead of salted butter?

Yes, you can use unsalted butter. Simply add a small pinch of salt to the dough to enhance the flavor.

→ What's the best way to keep the caramel from leaking out?

Ensure the dough fully covers the Rolos, sealing the edges well to keep the caramel inside during baking.

→ Can I substitute the sugar cookie mix with homemade dough?

Absolutely! A homemade sugar cookie dough with added cocoa powder works well for these cookies.

→ How do I know when the cookies are done?

Bake until the edges are set and the tops begin to crack. The centers should look slightly soft when removed from the oven.

→ How should I store these cookies?

Keep the cookies in an airtight container at room temperature for up to four days for maximum freshness.

→ Is chilling the dough necessary?

Yes, chilling helps prevent excessive spreading, ensuring the cookies stay thick and the centers remain gooey.

Chewy Chocolate Caramel Cookies

Buttery chocolate cookies with a melted caramel center. Irresistibly soft with a sweet finish.

Preparation Time
5 min
Cooking Time
10 min
Overall Time
15 min
Created By: Lili Clark

Category: Desserts

Skill Level: Beginner-Friendly

Cuisine Type: American

Output: 22 Serves (22 cookies)

Dietary Options: Vegetarian

Ingredients

01 17.5 ounce bag of sugar cookie mix
02 ¼ cup cocoa powder
03 ½ cup salted butter, softened
04 1 large egg
05 48 unwrapped Rolos
06 Sanding sugar or powdered sugar (optional garnish)

Steps

Step 01

Line two cookie sheets with parchment paper and set aside without preheating the oven.

Step 02

In a large mixing bowl, whisk together the sugar cookie mix and cocoa powder until combined.

Step 03

Using a hand or stand mixer, beat in the butter and egg until a thick dough forms.

Step 04

Scoop out a large ball of dough using a 1 ½ tablespoon cookie scoop, flatten into a disc, and place two unwrapped Rolos at its center. Gently form the dough into a smooth ball.

Step 05

Roll each formed ball in sanding sugar or powdered sugar if desired, then place it on the prepared cookie sheet.

Step 06

Cover the cookie sheets with plastic wrap and refrigerate for at least 30 minutes.

Step 07

Preheat the oven to 350°F (180°C) several minutes before baking.

Step 08

Remove the cookie sheets from the refrigerator and discard the plastic wrap. Bake the cookies for 10-15 minutes, or until the edges are set, and the tops begin to crack.

Step 09

Remove cookies from the oven and let cool for at least 5 minutes before transferring to a cooling rack or serving warm.

Required Tools

  • Parchment paper
  • Mixing bowl
  • Hand or stand mixer
  • 1 ½ tablespoon cookie scoop
  • Plastic wrap
  • Cooling rack

Allergy Information

Always check each ingredient for allergens, and consult a medical professional if unsure.
  • Contains gluten
  • Contains dairy
  • Contains eggs

Nutritional Information (per serving)

These details are shared for general guidance and don’t replace professional advice.
  • Calories: 177
  • Fats: ~
  • Carbohydrates: ~
  • Proteins: ~