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Honest Darling

life & style blog by Tessa Port

Dessert, Recipes • November 28, 2022

Rolo Sugar Cookies

Hello loves,

Cookie season is among us and if you’ve been a reader for a while, you know that I love cookies. I host a cookie swap every year before Christmas and love baking cookies! These Rolo sugar cookies are fun to make and a little different than your average sugar cookie.

Rolo sugar cookies

In case you’re looking for a classic sugar cookie recipe, may I suggest my Best Sugar Cookies? They are thick and pillowy and taste good even without frosting.  I also have a ton of other cookie recipes like my Soft Gingerbread Men Cookies or my Chai Sugar Cookies with Brown Butter Frosting or my Oatmeal Chocolate Chip Cookies.

Anyways, let’s get back to these rolo sugar cookies! First of all they are baked in a mini muffin tin. So they become sugar cookie “cups” that are soft and chewy. Then as soon as you take them out of the oven, a Rolo gets pushed into the center to create an ooey gooey chocolatey and caramel filled center. Really yummy! Let’s get to it.

Rolo sugar cookies Rolo sugar cookies

Rolo Sugar Cookies

Rolo sugar cookies
Print Recipe

Rolo Sugar Cookies

These soft and chewy sugar cookies cups get a Rolo pushed into the center right out of the oven to create an ooey gooey chocolatey and caramel filled center. Really really good!
Prep Time10 minutes mins
Cook Time10 minutes mins
Course: Dessert, Snack
Keyword: cookie cups, Rolo, sugar cookie
Servings: 18 cookies

Ingredients

  • 1/2 cup plus 1 tbsp unsalted butter, softened
  • 3/4 cup light brown sugar
  • 1 egg
  • 1/2 tsp vanilla
  • 1 1/2 cup plus 2 tbsp flour
  • 1/2 tsp baking soda
  • 18 rolos, unwrapped

Instructions

  • Preheat oven to 325°.
  • In a stand mixer on medium speed, beat the softened butter and brown sugar until fully combined and light and fluffy looking. About 2 minutes. Add in the egg and vanilla and beat until combined. Lower speed to medium low and add flour and baking soda. Mix until combined.
  • Using a cookie scoop if you have or just a spoon, scoop out some dough and roll into a ball. Should be about an inch and half or so. Place ball of dough into muffin tin just like that, do not flatten or press down. Continue until all dough is used. Makes about 18. Bake for 10-11 minutes until puffy and top is just starting to harden. Take out and immediately press rolos into the center of each cookie. Let cool completely before removing from tin to ensure the cookies hold shape. Enjoy!

As always, if you make these, be sure to tag me @tessa_port!

Tessa Honest Darling Signature
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