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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Snowy Lemon Balls

Best Ever Sugar Cookies

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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? ›

There are many reasons why your cookie dough may be crumbly. The most obvious culprit: not enough liquid to keep the dough together. Double check all liquid ingredients.

How do you keep Thumbprint Cookies from spreading? ›

Use a silicone baking mat or parchment paper. Coating your baking sheet with nonstick spray or butter creates an overly greasy foundation, causing the cookies to spread. I always recommend a silicone baking mat because they grip onto the bottom of your cookie dough, preventing the cookies from spreading too much.

How do you keep Thumbprint Cookies from cracking? ›

Make sure you roll the cookie dough balls into a smooth round ball. If there are cracks on the balls, then they're more likely to crack as you indent them. Also, avoid waiting too long after rolling them to indent them.

What does too much flour do to cookie dough? ›

Tough – For rolled cookies, your dough can become “tough” by adding too much flour to your pin or counter before rolling it out.

Why do my thumbprint cookies crumble? ›

Wet ingredients:

If you think your cookie dough is off, you may not have enough liquid in the recipe. Consider adding a touch more liquid such as melted butter, egg yolks, or a teaspoon of water. Add a teeny bit and see if that helps. Add more as needed until the dough holds together and is scoop-able.

What makes cookies fluffy and not flat? ›

Flour adds fluff and texture to the cookies. Adding too little flour can cause cookies to be flat, greasy, and crispy. Most recipes assume you'll use all-purpose, but if you want a lighter, crumblier cookie texture, choose one with a lower protein content such as cake-and-pastry flour.

Where do you store thumbprint cookies? ›

Store your baked thumbprint cookies in an airtight container at room temperature. There's no need to refrigerate. These cookies will keep for at least a week before starting to dry out and get crumbly.

Why are my thumbprint cookies melting? ›

Make sure your cookie sheet has cooled completely before placing your next batch of cookies, otherwise they'll start melting before they can start baking, and they're much more likely to spread.

How do you transport thumbprint cookies? ›

Stuff the tin or container with tissue paper (here's a festive option!), crumbled newspaper, or packing peanuts to keep the cookies snug. Place the tin or container into a shipping box and use more crumbled newspaper or other shipping materials if needed. Then send off!

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.

What does too much egg in cookie dough do? ›

If there isn't enough egg, your batter or dough may not be able to hold its structure or could end up overly dry or dense. On the other hand, if there is too much egg, your baked goods could lose their shape due to excess liquid, or have a rubbery (or even overly cakey) texture depending on the recipe.

What do overmixed cookies taste like? ›

Overmixing your batter can lead to runny cookies.

I mixed the batter more than I should have both during the creaming stage of the recipe and after adding the flour. As a result, the cookies came out light and airy, and I was able to taste the butter more prominently in this batch than in others.

What is the best flour for cookies? ›

All-Purpose Flour: The Versatile Choice

This balanced protein level makes it versatile enough to produce both soft and chewy cookies as well as slightly crisp ones. If you're looking for a safe bet or are new to cookie baking, all-purpose flour is your go-to option.

Why won't my cookies stay together? ›

Excess Sugar and Fat

Measuring is key in baking. If your cookie contains excess sugar or fat, it will spread while baking. If your first batch of cookies spreads, try adding a few tablespoons of flour to help thicken the remaining dough.

Why are my Thumbprint Cookies melting? ›

Make sure your cookie sheet has cooled completely before placing your next batch of cookies, otherwise they'll start melting before they can start baking, and they're much more likely to spread.

Why my cookies are breaking? ›

You Used the Wrong Kind of Flour

If you use cake or pastry flour, which are softer, your cookies will be fragile and crumbly. And if you use self-rising flour (which is a type of flour with the baking powder already mixed in), any number of things could go wrong.

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