Rolo Chocolate Chip Cookie Cups


Some days you just need a cookie. Some days you need 5 dozen.

Some days you also want chocolate and caramel. Those are the days you want these cookies: Rolo Chocolate Chip Cookie Cups.

Melty caramel, anyone?

stack of cookie cups with rolos inside on wood surface with one cut in half

When Jordan was about 1, she started talking. At some point that year, we realized she thought her name was You.

Me (to Jordan): Do you want a cracker?

Jordan: No, you.

Me: You want me to have a cracker?

Jordan: No, YOU.

Me: Okay, I’ll have a cracker.

Jordan: NO YOU!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

About the time the decibel level of the last “you” broke the windows, we realized she thought her name was You.

Moral of the story? Use your child’s name during their first year. Don’t just say “Do you want a cracker?” or “You are so cute” or “I love you!”

Believe me, they’re listening.


Want to know one of my only #momwin moments of Jordan’s food-related childhood? She was 13 months old the first time she had a cookie. We were at a restaurant at a mom’s group play group and they gave all the kids free cookies. I remarked this would be her first and everyone gasped.

I’m kind of glad I have that moment. Because yesterday she ate almost an entire bag of Jolly Rancher’s before I realized I’d said “yes” about 37 too many times.

If I let her, she’d eat this whole batch of Rolo Chocolate Chip Cookie Cups. I know I would!

Rolo Chocoloate Chip Cookie Cups - perfect homemade cookies and melty Rolos!

Like I said, sometimes you feel like a cookie. Last week I sure did. #longstory

And what’s better than a cookie? A cookie cup.

What’s better than a cookie cup? A cookie cup with a Rolo on top.

These are like blossom cookies but they’re made in mini muffin pans and you can press your favorite candy on top. They’re pretty much my favorite way to eat chocolate chip cookies.

This chocolate chip cookie base is my favorite recipe. I used it to make bakery style XL chocolate chip cookies, chocolate chip cookie cupcakes, toffee chocolate chip cookies, and orange chocolate chip cookies. It’s a recipe that I’ve always gotten rave reviews about, so why change a thing?

Except this time I did change something: I didn’t brown the butter. Forgive me? I was doing approximately 1,342 other things that same day (including a visit to the Apple Store, my first of two) and didn’t take the step. But you know what? It didn’t matter. The cookie cups are amazing with just melted butter.

Melted butter is my key to the perfect chocolate chip cookie. Melted butter and both granulated and brown sugar, that is. When you add the sugars to the warm butter, the cookie gets a caramelized taste. I’ve never been able to replicate it with softened butter.

Beware though, because this recipe uses melted butter you must chill it. Since the cookies are baked in mini muffin pans, however, the chilling time is cut drastically. That’s why I love baking cookies in mini muffin pans. No need to worry about spreading!

When they come out of the oven and are still hot, you press a Rolo on top. Let everything cool completely, then remove the cookies from the muffin pans. If you store these at room temperature, the Rolos stay soft. Soft and gooey Rolos are a good thing.

Rolo Chocoloate Chip Cookie Cups - perfect homemade cookies and melty Rolos!

Especially in chocolate chip cookie cups!

Rolo Chocolate Chip Cookie Cups

The perfect chocolate chip cookie recipe is made in a mini muffin pan and then the hot cookie is topped with a Rolo for a melty caramel cookie cup!
Yield 5 dozen
Serving Size


  • 2 sticks butter melted
  • 3/4 cup granulated sugar
  • 1 cup light brown sugar
  • 2 large eggs
  • 1 tablespoon pure vanilla extract
  • 1 teaspoon baking soda
  • 3 1/4 cups all-purpose flour
  • 1/4 teaspoon salt
  • 1 1/2 cup mini chocolate chips
  • 60 Rolo candies unwrapped (from about 2-12 ounce packages)
  • TIP: use a packaged cookie dough refrigerated or a mix to make these even easier and use ANY kind of candy you want!


  • Pour butter into an electric mixer fitted with paddle attachment. While still hot, add both sugars and mix on low until combined. Let sit to cool for a few minutes.
  • While butter mixture is cooling, combine flour, baking soda, and salt in a medium bowl. Stir and set aside.
  • Turn mixer (with butter mixture bowl attached) on low. Add eggs, one at a time, mixing completely. Mix in vanilla extract. Add flour mixture to the wet ingredients and mix until combined. Stir in chocolate chips.
  • Spray mini muffin pans with nonstick cookie spray (I like the kind with flour for these). Scoop 1-1 1/2 tablespoons of dough into each cavity. Chill the pans for at least 1 hour.
  • Preheat oven to 350°F. Bake cookie cups for about 9-11 minutes (the outside will start to turn a golden color when done).
  • When the cookie cups come out of the oven, press one Rolo into the center of each. Let cool completely in pans before removing (let the Rolo re-harden or it will collapse). Cookies should pop out easily with the aid of a knife.
  • Store in an airtight container for up to 4 days or freeze for up to 1 month.

Nutritional information not guaranteed to be accurate

Chocolate Chip Cookie Cake – top with your favorite candy!

Bakery Style Chocolate Chip Cookies

Easy Turtle Chocolate Chip Cookies

Easy 2 ingredient Junior Mint Chocolate Chip Cookies

Sweets from friends:
Strawberry Sugar Cookie Cups by Julie’s Eats and Treats
Salted Caramel Chocolate Chip Cookie Cups by Diethood
Cheesecake Caramel Pumpkin Cookie Cups by Something Swanky

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  1. Great variety, neighbor girls (10 &14)help make, they had a ball deciding which candy to put in cookies. We used 2 roll grenade cookie dough.

    1. The caramel won’t be creamy regardless of whether you freeze them – they’ll be the same consistency as the Rolo (semi-soft, hard, not drippy gooey). You can freeze them though, just be sure to serve them only once they’ve thawed.