Rolo Cookies

Stuffing candy into cookies is one of those ideas that sounds too simple to be good, but then you bite into a warm cookie and hit that pocket of melted caramel and suddenly it all makes sense. These Rolo cookies use boxed sugar cookie mix doctored up with cocoa powder to save time, then you hide two Rolos in the center of each cookie before baking. When they come out of the oven, the caramel inside is all gooey and melted while the chocolate gets soft, creating this ridiculous combination that makes people eat way more cookies than they probably should. I started making these when my son's teacher asked parents to send treats for the class party and I needed something that looked homemade without actually requiring me to bake from scratch at 10pm the night before. Every kid in that class apparently went home talking about the cookies with chocolate inside, and now I get requests from other parents wanting the recipe. My son acts like I'm some kind of celebrity chef because his friends keep asking about "those caramel cookies your mom makes."

My neighbor Linda is one of those people who bakes everything from scratch and judges anyone who uses shortcuts. She came to a PTA meeting where I'd brought these cookies, ate one, and then came over to ask for my "from scratch" recipe because they were so good. When I told her they started with boxed mix, she got quiet for a second and then admitted she'd been making cookies the hard way for years when she could have been doing this. Now she makes them constantly for her grandkids and has stopped being so judgmental about convenience baking. Her husband told me later that she makes double batches and hides half of them from him in the back of the freezer because he'll eat an entire batch in two days if she doesn't ration them out.

What Goes Into Them

• Sugar cookie mix: One 17.5-ounce bag.
• Cocoa powder: A quarter cup for chocolate flavor.
• Salted butter: One stick (8 tablespoons) softened to room temperature.
• Egg: One large egg for binding and texture.
• Rolos: 48 unwrapped candies (approximately two standard bags).
• Sanding sugar or powdered sugar: Optional, for coating the outside.

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Making These Cookies

Getting everything ready:

Line two large cookie sheets with parchment paper. Unwrap all 48 Rolos (2 per cookie).

Mixing the dough:

In a large bowl, whisk together the sugar cookie mix and 1/4 cup cocoa powder. Add the softened stick of butter and egg. Beat with a hand mixer until a thick, uniform, chocolate dough forms. The dough should be dense.

Stuffing with Rolos:

Use a 1.5-tablespoon scoop to portion the dough. Flatten the dough into a 1/4-inch thick disc. Place **two unwrapped Rolos** in the center. Gently bring the edges of the dough up and around the candies, pinching and smoothing the seam to form a complete ball with no exposed candy.

Optional sugar coating:

Roll the stuffed dough ball through sanding sugar or powdered sugar for coating, if desired. Place the balls 2 inches apart on the prepared cookie sheets. Yields 22–24 cookies.

Chilling the dough:

Cover the cookie sheets loosely with plastic wrap and chill in the refrigerator for at least **30 minutes** (1 hour is better). This is crucial for preventing spreading.

Baking to perfection:

Preheat oven to 350 degrees F. Bake one sheet at a time for **10–15 minutes**. The edges should be set, and the tops may have cracks, but the centers should still look slightly soft. Do not overbake.

Cooling:

Let the cookies sit on the hot cookie sheet for a full **5 minutes** to firm up. Then, carefully transfer them to a wire cooling rack.

I skipped the chilling step once when I was in a hurry and wanted cookies immediately. Those cookies spread so much in the oven that they turned into flat, lacy discs with the Rolos completely exposed on top, leaking caramel everywhere. They tasted fine but looked terrible and weren't really what I was going for. Now I force myself to wait through that 30-minute chill time even when I'm impatient, because the results are so much better with cookies that hold their shape and keep the candy tucked inside.

Serving These Cookies

Serve these cookies while they are still slightly warm to maximize the melted, gooey caramel center. They are perfect for school parties, bake sales, and holiday exchanges. Pair with cold milk or hot coffee. They are rich enough that one or two cookies usually satisfies a sweet tooth.

Different Ways to Try Them

• Use **peanut butter cookie mix** instead of sugar cookie mix for a chocolate peanut butter version.
• Stuff them with **Milky Way Midnight pieces** instead of Rolos for dark chocolate and caramel.
• Add a **pinch of sea salt** on top right after baking for a salted caramel effect.
• Mix some **instant espresso powder** into the dough for mocha cookies.
• Use **white chocolate chips** mixed into the dough along with the Rolos.
• Roll the cookies in **crushed graham crackers** instead of sugar.

Keeping Them Fresh

• Keep at **room temperature** in an airtight container for up to 5 days; they remain soft and chewy.
• Store in the refrigerator if your kitchen is hot, but let them return to room temperature before eating.
• **Baked cookies freeze well** for up to 3 months.
• **Unbaked stuffed dough balls freeze beautifully:** Freeze until solid, then transfer to a freezer bag. Bake frozen, adding 2–3 minutes to the baking time.

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I've made these Rolo cookies probably a hundred times at this point for every occasion imaginable. They never fail to get enthusiastic reactions, especially from kids who lose their minds over the candy hidden inside. The boxed mix shortcut means I can throw these together on a weeknight without it feeling like a huge project. The Rolos elevate everything and make people think you did something way more complicated than you actually did. These have earned their permanent spot in my baking rotation, joining that small group of recipes I make constantly because they're reliable, easy, and consistently make people happy every single time!

Frequently Asked Questions

→ Why do I need to chill the dough?

Chilling keeps the cookies from spreading too flat while baking. It also helps the Rolos stay inside instead of melting out through the dough.

→ Can I use homemade cookie dough instead of a mix?

Sure! Any basic sugar cookie dough recipe will work. Just add the cocoa powder to make it chocolate flavored.

→ How do I keep the Rolos from leaking out?

Make sure the dough is sealed completely around the candies with no cracks. Chilling the dough also helps keep everything contained while baking.

→ Can I use a different candy instead of Rolos?

Yes! Caramel-filled Hershey Kisses, peanut butter cups, or even chocolate truffles would all work great in these cookies.

→ Should I serve these warm or cool?

They're amazing warm when the caramel is gooey and melty, but they're also good at room temperature. If they cool completely, you can warm them in the microwave for a few seconds.

→ Can I freeze these cookies?

You can freeze the baked cookies for up to 3 months. You can also freeze the dough balls before baking and bake them straight from frozen - just add a couple extra minutes to the baking time.