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

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Chocolate Rolo Thumbprint Cookies Recipe (2024)

FAQs

Why do my thumbprint cookies spread so much? ›

If your butter is under mixed, it won't have the air pockets to hold it's shape. If it's over-mixed, the air pockets decrease in size and are unable to hold their shape in the oven—causing your cookies to spread. It's best to cream butter and sugar on medium speed for 2 to 3 minutes.

Why are my thumbprint cookies falling apart? ›

Do not press too hard or the cookie will fall apart. Fill each cookie with 1/2 teaspoon of jam. Bake, then let cool: Bake for 12 to 15 minutes or until slightly firm.

Why are my thumbprint cookies cracking when putting thumbprint? ›

To help avoid cracking when making the indentations in the dough balls: Make sure the dough balls are very smooth on the outside. Press into the dough very gently/slowly.

How to make cookies more moist after baking? ›

Add a Slice of Bread to the Container

You might find it surprising, but adding a slice of bread to your cookie container can help keep the cookies moist for a while!

Can you put cookies back in the oven after they have cooled? ›

When cookies turn out underbaked, they can still be salvaged. Quickly return them to the oven if they're fresh, or reheat at a lower temperature if they've cooled. For cookies too soft to crisp, repurpose them in desserts like parfaits or trifles. These strategies ensure no batch of cookies is wasted.

Does thumbprint cookie dough need to be refrigerated? ›

It is important that you don't chill this dough. The butter solidifies and it will make the dough crack and fall apart when shaped and pressed with your thumb. Shape and bake immediately after mixing, or if you accidentally chilled the dough, allow it to warm up to room temperature before continuing.

How do you package thumbprint cookies? ›

Line the bottom and sides of a square or rectangular airtight tin with corrugated paper. Fold short lengths in half for dividers. Envelop your cookies in tissue paper, buffer them with corrugated paper tubes, or protect them using accordion-folds of paper. You can also tie a stack of cookies with baker's twine.

Why do people poke fork holes in sugar cookies? ›

You can use a fork or a dough docker to prick small holes all over the surface of the dough. By venting the steam, docking keeps the dough from billowing or heaving as it bakes. It's an important step for crisp cookies or that are baked all in a single sheet and not cut up until they come out of the oven.

How do I stop my thumbprint cookies from spreading? ›

Chilling Cookie Dough

If the cookie dough you are working with is on the wetter side or sticky, I always recommend chilling for 30 minutes to 2 hours. The colder the dough is, the less the cookies are going to spread as they are baked in the oven.

Why did my thumbprint cookies come out flat? ›

If your cookies repeatedly turn out flat, no matter the recipe, chances are your oven is too hot. Here's what's happening. The butter melts super quickly in a too-hot oven before the other ingredients have firmed up into a cookie structure. Therefore, as the butter spreads so does the whole liquidy cookie.

Do thumbprint cookies mail well? ›

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

Why did my cookies spread out and flatten? ›

If your cookies repeatedly turn out flat, no matter the recipe, chances are your oven is too hot. Here's what's happening. The butter melts super quickly in a too-hot oven before the other ingredients have firmed up into a cookie structure. Therefore, as the butter spreads so does the whole liquidy cookie.

Why are my crinkle cookies spreading too much? ›

One of the most common causes of cookie spread is that the fat is too warm. Make sure to chill your dough thoroughly if the recipe calls for it. If you're forming dough balls and the dough is too sticky to work with, this is a sign that your dough may be too warm. Try chilling the dough for at least 15 minutes!

Why are my cookies so puffed up? ›

A spread with less fat, diet "margarines" or spreads in tubs contain have too much water. The water creates steam, causing the cookies to puff. Low protein flours, such as cake flour, absorb less water, leaving excess water to create steam, which causes the cookies to puff.

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