Rolo Chocolate Chip Cookie Cups

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Chocolate Chip Cookie Cups are a from scratch version of my favorite cookie cup recipe. These are my FAVORITE chocolate chip cookie – baked into a mini muffin pan!

These are fantastic plain, with frosting, or with Rolos or any other candy pressed on top.

Close up of chocolate chip cookie cups stacked on top of eachother on a wood cutting board

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

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

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

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

Melty caramel, anyone?

BUT! These are fantastic with peanut butter cups…or frosting…or even plain. If you want to make cookie cups from scratch then you’re in the right place.

Close up of chocolate chip cookie cups stacked on top of eachother with top cut in half to show rolo filling

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. It’s the ONLY recipe I use – so why change a thing?

What makes these the best cookies?

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.

Other than that, these have the normal cookie ingredients: egg, baking soda, flour, vanilla.

You can make them in ONE bowl with a spoon – no mixer needed!

You have two choices when you bake chocolate chip cookies as cookie cups:

  1. Mini Muffin Pan
  2. Cupcake Tin

I’ve made this recipe in both (remember those Cookie Cupcakes years ago?) but I love the bite size cookie that a mini muffin pan makes.

Make sure to spray your muffin tins with nonstick spray and only put about 1 tablespoon in each cavity.

Chocolate chip cookies cups on a wood cutting board

So many choices for flavors:

Candy Topping

When they come out of the oven and are still hot, you press a Rolo on top. Or, use a mini peanut butter cup, Hershey’s Kiss, or any small candy.

Let everything cool completely, then remove the cookies from the muffin pans. It’s best to wait until they are cool to remove them because the candy won’t be stable (it’ll melt from the heat of the cookie).

If you store these at room temperature, the Rolos stay soft. Soft and gooey Rolos are a good thing.

Frosting Topping

These are also fun topped with frosting! Here are some of my favorites:

Most definitely! I always freeze these so I have cookie cups whenever I want. They’re great for holiday giving that way too.

Have you made this recipe?

Tag @crazyforcrust on Instagram or hashtag it #crazyforcrust

The perfect chocolate chip cookie recipe is made in a mini muffin pan and then the hot cookie is topped with a Rolo or any candy or frosting.
Prep Time 15 minutes
Cook Time 10 minutes
Total Time 25 minutes
Yield 60 cookies
Serving Size 1 cookie

Ingredients

  • 1 cup unsalted butter , melted
  • 2/3 cup granulated sugar
  • 1 cup packed brown sugar
  • 2 large eggs
  • 2 teaspoons pure vanilla extract
  • 1 teaspoon baking soda
  • ½ teaspoon salt
  • 3 cups all-purpose flour
  • 1 ½ cup mini chocolate chips
  • 60 Rolo candies unwrapped (from about 2-12 ounce packages) or any other candy

Instructions

  • 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.
  • Place melted butter in the bowl of a stand mixer fitted with the paddle attachment (or a large bowl if using a hand mixer). Add granulated and brown sugars and mix on low speed until the mixture is smooth. Mix in egg and vanilla extract and mix on medium speed until combined.
  • Mix in baking soda and salt, then slowly mix in flour and mix just until the batter is smooth and comes together. Be sure to scrape the sides of the bowl during mixing. Slowly mix in chocolate chips.
  • Spray mini muffin pans with nonstick cookie spray (I like the kind with flour for these). Scoop 1-1 ½ tablespoons of dough into each cavity. Chill the pans for 20 minutes.
  • 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 candy 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.
  • Or, skip the candy, let them cool then remove them from the pans and frost with desired frosting.
  • Store in an airtight container for up to 4 days or freeze for up to 1 month.

Nutrition Information

Serving: 1cookie | Calories: 97kcal | Carbohydrates: 14g | Protein: 1g | Fat: 4g | Saturated Fat: 3g | Cholesterol: 14mg | Sodium: 44mg | Potassium: 14mg | Fiber: 1g | Sugar: 9g | Vitamin A: 113IU | Vitamin C: 1mg | Calcium: 11mg | Iron: 1mg

Nutritional information not guaranteed to be accurate

Course Dessert
Cuisine American
Keyword cookie
Close up of chocolate chip cookie cups stacked on top of eachother on a wood cutting board with recipe title on top

Chocolate Chip Cookie Cups are a great way to make cookies in a muffin tin! This recipe makes mini muffin sized cookies and you can fill them with candy like Rolos!

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62 CommentsLeave a comment or review

  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.