The second I bit into one of these Rolo Cookies while I was testing them, I knew they were going straight onto my all-time favorite cookie list. The chocolate cookie base has a flavor that instantly took me back, reminding me of the cookies I used to have at a friend’s house growing up. I love when food does that, when one bite brings back a memory you had not thought about in years. These cookies are soft, chewy, rich, and then you get that little surprise of caramel in the center from the Rolo. I already know you are going to see this cookie dough base show up in a few more recipes around here because I am definitely not done with it yet.
If you are already in baking mode, you might as well keep going. Try my White Chocolate Raspberry Cookies, Ranger Cookies, or Cornflake Cookies next. These are the kinds of desserts I make when a plain chocolate chip cookie just is not going to cut it.
Stephanie’s Tips
• Completely cover the Rolo with cookie dough. Any cracks or openings give the melted caramel an escape route.
• Do not skip chilling the dough. It helps keep the cookies thick and prevents them from spreading too much.
• Cream the butter and sugars for the full 3 to 4 minutes. This helps give the cookies a lighter texture.
• Mix the flour mixture in just until combined. Once the flour goes in, you do not want to keep beating the dough.
• The caramel will be the gooiest while the cookies are still slightly warm.
• If you want that melty center again the next day, warm a cookie in the microwave for just a few seconds.
Equipment
- Measuring cups and spoons
- Whisk
- Two sheet pans
- Parchment paper
- Stand mixer or Hand mixer
- Cooling rack
- Mixing bowl
- Scoop or large spoon
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Ingredients
- Cocoa powder: Use natural unsweetened cocoa powder for these cookies. It gives them plenty of chocolate flavor and works with the baking soda in the recipe.
- Butter: Let the butter soften before creaming it with the sugars. You want it soft enough to mix easily, but not melted.
- Brown sugar: Brown sugar helps keep the cookies soft and chewy.
- Granulated sugar: Using both granulated and brown sugar gives you a good balance of texture and sweetness.
- Eggs: Room-temperature eggs blend into the creamed butter mixture more easily.
- Vanilla extract: Two teaspoons add plenty of vanilla without taking over the chocolate flavor.
- Rolos: The important part. One whole Rolo gets tucked inside every cookie, giving you that chocolate caramel center.
Directions
Start by mixing the flour, cocoa powder, baking soda, and salt together.
Cream the softened butter with both sugars until light and fluffy, then mix in the eggs and vanilla.
Slowly add the dry ingredients just until the dough comes together, then chill it for one hour.
Scoop the dough into balls and press one Rolo into the center of each. Completely cover the candy with dough before placing the cookies on the prepared pans.
Bake until the edges are set, then let the cookies cool before transferring them to a cooling rack.
How do I serve Rolo Cookies?
- Honestly, these do not need much. Eat them slightly warm when the chocolate and caramel center is still gooey, grab one with your coffee, or add them to a cookie tray during the holidays. A cold glass of milk does not hurt either.
FAQs (Because Life’s Too Busy for Guesswork)
Yes. Chopped pecans or walnuts work well with the chocolate and caramel flavors. I would mix them into the dough rather than pressing them deeply into the top of the formed cookie so you do not create a hole around the Rolo.
Make sure the Rolo is completely enclosed in cookie dough with no cracks or thin spots. Smooth the dough around the candy before placing the cookie on the baking sheet.
Chilling the dough also helps the cookies hold their shape while baking.
The caramel will stay chewy, but it will not stay as gooey as it is when the cookies are warm. For that melty caramel center again, microwave a cookie for just a few seconds before eating it.
Chilling firms up the butter in the dough so the cookies do not spread too quickly in the oven. It also makes the dough easier to wrap around the Rolos and helps keep the candy enclosed while the cookies bake.
Yes. Make the cookie dough, cover it tightly, and refrigerate it until you are ready to bake. Let it sit at room temperature for a few minutes if it becomes too firm to scoop and shape.
Yes. Form the dough around the Rolos and freeze the cookie dough balls on a sheet pan until firm. Transfer them to a freezer-safe container or bag.
Bake from frozen, adding a couple of extra minutes if needed.
What are substitutions that I can make?
- Unsalted butter: Salted butter can be used. Reduce the added salt to about 1/4 teaspoon.
- Light brown sugar: Dark brown sugar will work, but it will give the cookies a slightly deeper molasses flavor.
- Vanilla extract: Vanilla bean paste can be substituted at a 1:1 ratio.
- All-purpose flour: A 1-to-1 gluten-free baking flour may work, but I would not automatically add another egg. Different gluten-free flour blends behave differently, so I would only include this substitution once it has been tested with this particular recipe.
- Nuts: Chopped pecans or walnuts can be added to the cookie dough if you want some crunch.
How should I store Rolo Cookies?
- Store completely cooled Rolo Cookies in an airtight container at room temperature for up to one week.
- For longer storage, place them in a freezer-safe airtight container and freeze for up to 3 months. Let them thaw at room temperature before serving.
- The caramel center will become firmer as the cookies cool. Warm an individual cookie in the microwave for a few seconds if you want the center soft and gooey again.
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Rolo Cookies
Equipment
- Measuring cups and spoons
- 2 Sheet pans
- Parchment paper
- Medium mixing bowl
- Mixer and bowl
- Cookie scoop or large spoon
- Cooling rack
Ingredients
- 2 cups all-purpose flour
- 1 cup cocoa powder
- 1 teaspoon baking soda
- 1/2 teaspoon salt
- 1 cup unsalted butter softened
- 1 cup light brown sugar packed
- 1/2 cup granulated sugar
- 2 large eggs at room temperature
- 2 teaspoons vanilla extract
- 32 Rolos candies
Instructions
- Preheat the oven to 350°F and line two sheet pans with parchment paper.
- In a medium mixing bowl, combine the flour, cocoa powder, baking soda, and salt.
- In the mixer bowl, cream the butter, brown sugar, and granulated sugar until light and fluffy, 3 to 4 minutes. Add the eggs, one at a time, then mix in the vanilla extract. Slowly mix in the flour mixture just until incorporated. Place the dough in the refrigerator for 1 hour.
- Scoop the dough into 1-inch balls and press a Rolo into the center of each ball, covering the Rolo with the cookie dough.
- Place the cookies on the sheet pans about 2 inches apart.
- Bake for 10-12 minutes until the edges are set. Transfer the cookies to a cooling rack and allow them to cool.
Notes
- Use natural unsweetened cocoa powder.
- Chill the cookie dough for 1 hour before shaping the cookies.
- Completely cover each Rolo with cookie dough so the caramel does not leak out.
- Leave about 2 inches between cookies on the baking sheet.
- Bake just until the edges are set so the centers stay soft.
- The caramel center is gooiest while the cookies are still slightly warm.
- Store cooled cookies in an airtight container at room temperature for up to 1 week.
- Freeze baked cookies for up to 3 months.
