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Rolo Cookies are a from scratch version of my favorite cookie cup recipe. These are my FAVORITE chocolate chip cookie – baked into a mini muffin pan!

stacked cookie cups with a Rolo baked in.


Table of Contents

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?

If you want to make Rolo cookie cups from scratch then you’re in the right place.

stacked cookie cups with a Rolo baked in.

What makes these the best cookies?

  • 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?
  • 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!

How to bake Rolo Cookies

  1. Make sure to spray your muffin tins with nonstick spray and only put about 1 tablespoon in each cavity.
  2. Mix up your cookie dough as directed – just stir together melted unsalted butter with brown sugar and granulated sugar. Stir in egg, vanilla, salt, and baking soda. Stir in flour and chocolate chips.
  3. Press one tablespoon dough into each muffin pan cavity. Chill 20 minutes.
  4. Bake in an oven preheated to 350°F.
  5. Press a Rolo into the warm cookie cups when they come out of the oven. Cool, then remove from pans.
stacked cookie cups with a Rolo baked in.

Tip From Dorothy

Expert Tips

  • Don’t skip greasing your pans. Nonstick cooking or baking spray works just fine, or use butter or shortening.
  • Let them cool completely before removing. To remove, use a butter knife to help pop them out.
  • You know Rolo Cookies are done baking when they’ve just lost their glossy sheen.
  • You can top these with any candy – not just Rolos! Use peanut butter cups, Hershey’s Kisses, or anything!
  • You can even top these with frosting: Vanilla Buttercream Frosting, Cream Cheese Frosting, or Peanut Butter Frosting would be fantastic!

FAQs

Can you freeze Rolo Cookies?

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

stacked cookie cups with a Rolo baked in.

Rolo Cookies Recipe

4.06 from 99 votes
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
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Ingredients
 

  • 1 cup (226g) unsalted butter , melted
  • ⅔ cup (134g) granulated sugar
  • 1 cup (200g) packed brown sugar
  • 2 large eggs
  • 2 teaspoons pure vanilla extract
  • 1 teaspoon baking soda
  • ½ teaspoon salt
  • 3 cups (372g) all-purpose flour
  • 1 ½ cups mini chocolate chips
  • 60 Rolo candies unwrapped (from about 2-12 ounce packages) or any other candy
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Instructions

  • 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 1/2 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.

Recipe Notes

  • Don’t skip greasing your pans. Nonstick cooking or baking spray works just fine, or use butter or shortening.
  • Let them cool completely before removing. To remove, use a butter knife to help pop them out.
  • You know Rolo Cookies are done baking when they’ve just lost their glossy sheen.
  • You can top these with any candy – not just Rolos! Use peanut butter cups, Hershey’s Kisses, or anything!

Recipe Nutrition

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
Author Dorothy Kern

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Dorothy Kern

Welcome to Crazy for Crust, where I share recipes that are sometimes crazy, often with a crust, and always served with a slice of life.

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4.06 from 99 votes (96 ratings without comment)

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77 Comments

  2. bahahaa that’s so cute that Jordan thought her name was “You”!!

    and I lovelovelove these cookie cups-the texture is major and omg melty caramel!

    Reply

  4. I love your cookie-in-a-cup idea! And how funny, about Jordan! My daughter had no sweets until she was almost 3 years old, and when she was 2 I used to get compliments from women at the grocery store check stand (“she’s not asking for candy!” – little did they know that she didn’t know what it was. I miss those days!)

    Reply

  5. Ooo! Rolos! I love Rolos! Especially in cookies! These cookie cups look so good, Dorothy! Pinned!

    Reply