Chocolate Rolo Thumbprint Cookies Recipe (2024)

Published: · Modified: by Megan Porta · This post may contain affiliate links.

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As if Chocolate Thumbprint Cookies weren’t delicious enough! Adding Rolos, that are caramel filled, to the centers of each chocolate cookie, sends them into another world. These soft and chewy cookies are great for holiday baking or any celebration throughout the year!

Chocolate Rolo Thumbprint Cookies Recipe (1)

Whilst rinsing conditioner out of my hair in the shower yesterday, I realized that….CHRISTMAS IS NEXT WEEK! How the heck!There has been an unusual time warp this year due to the unseasonably warm weather we continue to experience here in Minnesota (and likely everywhere). In my tired little brain, it is approximately October 12th. Not December 15th. Thankfully I have these two cute little humans living in my home who remind me DAILY how many days left until the BIG day. If it weren’t for them, I probably would have begun Christmas shopping on or around Valentine’s Day.

Chocolate Rolo Thumbprint Cookies Recipe (2)

Also thanks to those cuties, I continue to bake! MORE CHRISTMAS COOKIES, MOMMY! As you please.

PRIZE WINNING COOKIES!

This particular recipe was created QUICKLY in order to make the deadline for Dan’s work cookie contest. It won 2nd place! I literally came up with the recipe, made them and did the dishes all in less than one hour. If you’re on the lookout for a quick and easy cookie, look no further!

Do you have a prize winning cookie recipe? We’d love for you to post it on our Pip and Ebby Facebook page to tell us about it OR message us!

MAKE A BATCH OF CHOCOLATE ROLO THUMBPRINT COOKIES

Having a favorite cookie loaded with chocolate flavor and all kinds of melted caramel is a necessity!

  • Preheat oven to 350 degrees F. Line two large baking sheets with parchment and set aside.

  • In a large bowl, combine salted butter, sugar and cocoa powder. Mix until creamy. In a separate bowl, combine the flour, baking soda and salt and stir until combined. Gradually add the flour mixture to the mixing bowl and mix until incorporated.

  • Roll dough into 1 1/2-inch balls and place onto baking sheets. Gently press your thumb into the center of each ball until indentation has formed.

  • Place a Rolo candy onto the top of each indentation and bake in the preheated oven for 10-15 minutes, or until the Rolos start leaking caramel. Remove the cookies from the pan and let them cool completely on a cooling rack for 5 minutes, then enjoy!

ROLO CANDIES UNWRAPPED – A TIME SAVER

When I created these cookies, I had the pleasure of unwrapping each gold foiled chocolate individually. It wasn’t a hard call – these cookies were worth the effort! But now, you can actually BUY a bag of Unwrapped Rolo treats and save yourself the time. Isn’t the candy world good to us?!

Is anyone else’s mental calendar waaaaaay off this year? I’m feeling a touch of insanity because of it. Before I know it, it will all be over and my head will be spinning violently. I am officially, as of this very moment, hitting my RESET button in order to fully enjoy and appreciate the next few weeks.

Enjoy these cookies AND the rest of your week! Thanks for being here!

WHETHER YOU ARE LOOKING FOR JUST A DELICIOUS COOKIE OR A GREAT HOLIDAY COOKIE, YOU’VE COME TO THE RIGHT PLACE!

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Chocolate Rolo Thumbprint Cookies Recipe (3)

Chocolate Rolo Thumbprint Cookies Recipe (4)

Chocolate Rolo Thumbprint Cookies

As if Chocolate Thumbprint Cookies weren’t delicious enough! Adding Rolos, that are caramel filled, to the centers of each chocolate cookie, sends them into another world. These soft and chewy cookies are great for holiday baking or any celebration throughout the year!

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Course: Dessert

Cuisine: American

Prep Time: 15 minutes minutes

Cook Time: 20 minutes minutes

Servings: 15 cookies

Calories: 247.59kcal

Author: Megan Porta

Ingredients

  • 1 cup butter softened (2 sticks)
  • 2/3 cup sugar
  • 1/3 cup cocoa powder
  • 2 cups flour
  • 1/2 tsp. baking soda
  • 1/2 tsp. salt
  • 18 Rolo chocolate candies unwrapped

Instructions

  • Preheat oven to 350 degrees F. Line two large baking sheets with parchment and set aside.

  • In a mixing bowl, combine butter, sugar and cocoa powder. Mix until creamy. In a separate bowl, combine the flour, baking soda and salt and stir until combined. Gradually add the flour mixture to the mixing bowl and mix until incorporated.

  • Roll dough into 1 1/2-inch balls and place onto baking sheets. Carefully press your thumb into the center of each ball until indentation has formed.

  • Place a Rolo into each indentation and bake in the preheated oven for 10-15 minutes, or until the Rolos start leaking caramel. Let cool for 5 minutes and enjoy!

Nutrition

Calories: 247.59kcal | Carbohydrates: 27.89g | Protein: 2.6g | Fat: 14.26g | Saturated Fat: 8.93g | Cholesterol: 33.51mg | Sodium: 224.08mg | Fiber: 0.88g | Sugar: 13.81g

Did you make this recipe?If you loved this recipe, please rate the recipe and leave a comment below!

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Reader Interactions

Comments

  1. Chocolate Rolo Thumbprint Cookies Recipe (6)Diane

    I already love Rolo candies by themselves, so the idea of melting them on top of cookies is just… yes please.

    Reply

  2. Chocolate Rolo Thumbprint Cookies Recipe (7)Deb

    Yum! I purchased several bags of rolos after Halloween on mega clearance. These will be a great addition to the cookie plate at our house!

    Reply

  3. Chocolate Rolo Thumbprint Cookies Recipe (8)Warm Vanilla Sugar

    These little cookies look so tasty!! I love the Rolo used in the centre. Yum!

    Reply

Leave a Reply

Chocolate Rolo Thumbprint Cookies Recipe (2024)

FAQs

Why are my thumbprint cookies falling apart? ›

The dough should be chilled for at least 30 minutes, so that you can shape it into balls and indent without falling apart. Check that your oven temperature isn't too high.

How do you keep thumbprint cookies from spreading? ›

Storing your dough in the fridge helps to harden the fat and prevent your cookies from spreading. Allow it to chill in the refrigerator for 30 minutes.

Why are my thumbprint cookies cracking when putting thumbprint? ›

Thumbprints crack if the dough is too cold or pressed to aggressively. I recommend using your index finger and pressing firmly but make the indent slowly. I know they are called “thumbprints” but most people's thumbs are actually too big for this task and will crack the dough!

What happens if you add too much flour to cookie dough? ›

Too Much Flour

Our cookies didn't expand much from the rolled-up balls we put on the baking sheet. They also didn't brown as well as the other cookies. It doesn't take much—in this case, my mom and I added just 3/4 cup extra flour to the dough. The cookies tasted good, but were dry and definitely crumbly.

Do I need to refrigerate thumbprint cookies? ›

No. After baking, thumbprint cookies do not need to be refrigerated. To store them, simply save in an airtight container at room temperature. You can store them in the refrigerator if you prefer, but it's not necessary.

What is the secret to thick cookies? ›

A low proportion of sugar relative to flour reduces spread, keeping the cookies thick. A high proportion of mix-ins helps thicken the dough. Blending chocolate chip styles creates a more dynamic flavor. Overnight refrigeration hydrates the flour, again helping the cookies stay thick.

What makes cookies fluffy and not flat? ›

Try using baking powder instead of baking soda. Baking soda encourages spreading while baking powder puffs the cookies up. If your recipe calls for 1 teaspoon of baking soda, you would use 3 to 4 teaspoons of baking powder.

What happens if I put too much butter in my cookies? ›

Too much butter makes cookies turn out just as you'd expect: very buttery. This batch of cookies was cakey in the middle, but also airy throughout, with crispy edges. They were yellow and slightly puffy in the middle, and brown and super thin around the perimeter.

What is the shelf life of Thumbprint Cookies? ›

When does Thumbprint Cookies expire? When does Thumbprint Cookies expire? Thumbprint cookies, whether homemade or store-bought, generally maintain their best quality for up to 1 to 2 weeks at normal room temperature.

Do Thumbprint Cookies mail well? ›

Do Thumbprint Cookies ship well? Yes. Firm and sturdy cookies are the best type of cookies to ship, so our Thumbprint Cookies handle the trip well.

Can I freeze dough for Thumbprint Cookies? ›

Absolutely! Thumbprint cookies will either have their indentions made before or after baking. If that occurs before baking, you can do that before they're frozen so that they're ready to go when you're ready to bake them.

Should I use baking powder or baking soda for cookies? ›

Baking soda is typically used for chewy cookies, while baking powder is generally used for light and airy cookies. Since baking powder is comprised of a number of ingredients (baking soda, cream of tartar, cornstarch, etc.), using it instead of pure baking soda will affect the taste of your cookies.

What happens if I dont put enough flour in my cookies? ›

If your cookies are coming out looking flatter than you'd like, a little extra flour goes a long way. As Baking Kneads explains, flour not only prevents cookies from spreading too much, but it also gives them height.

What ingredient makes a cookie crumbly? ›

There are several reasons why the cookies may have become dry and crumbly but the two most likely are that either the cookies were baked for too long or too much flour was added to the dough.

Why did my cookies rise and then fall? ›

Dough that's too airy.

The goal, usually, is to only incorporate the two ingredients without reaching the "light and fluffy" stage. When you mix the butter and sugar together at high speed or for too long, you'll aerate the dough excessively, causing the cookies to rise—and then fall—in the oven.

How do you make cookies stick together? ›

Put the cookie pieces together on the baking sheet. Gently mush the edges together to "glue" the cookies into each other as they bake. Sometimes gluing the cookies together is enough, if they are interlocked and share enough edges. Sometimes though... you need to add some "tape."

Why are my cookies broken? ›

Wrong butter temperature

Butter that is too soft or melted will make it hard for your cookies to hold their shape. On the other hand, incorporating cold butter into a mixture of dry ingredients is troublesome and difficult. Here's a hack: Cut your butter into cubes before letting them soften at room temperature.

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