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

Gingerbread Cookies

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? ›

Also, don't make your cookies too big, thumbprints are smaller cookies. And most importantly, make sure you you chill the dough! After you form the cookies, place the unbaked cookies in the freezer for at least 30 minutes before baking. This will prevent them from spreading.

How do you keep thumbprint cookies from cracking? ›

The best way to keep thumbprint cookies from cracking and to keep them soft is to use cornstarch. In this recipe, I use just the right amount of cornstarch so you have a buttery shortbread cookie that doesn't crack.

What happens if you add too much flour to cookies? ›

If your cookies come out looking more like biscuits, you've likely added 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.

Why are my thumbprint cookies dry? ›

Overmixing the dough

If you overmix the dough, the cookies will be dry and crumbly. The best way to fix this is to add more liquid to the dough. This can be done by adding milk, water, or even melted butter. You may also need to add more flour to the dough if it is too wet.

How long should you chill cookie dough? ›

As a general rule of thumb, you should refrigerate cookie dough for at least 30 minutes and up to 24 hours. More than that, and you won't see a noticeable difference in the final product. Once the dough has chilled, let it warm up at room temperature until it's just pliable (about 5 to 10 minutes).

What makes cookies fluffy and not flat? ›

Room temperature butter is just the right consistency to incorporate air when it's creamed with sugar. These trapped air pockets result in risen, fluffy cookies. If the butter is any warmer, it won't incorporate enough air and your cookies will have less rise.

What is the shelf life of thumbprint cookies? ›

What is the Shelf Life of Thumbprint Cookies? You can either store your cookies at room temperature or in the refrigerator. They will stay fresh for up to 3 days on the counter and for up to 5 in the fridge. Whether you chill them or choose not to, you should keep them in an airtight container.

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.

Does adding more butter make cookies softer? ›

Also, underbaking them by a minute or 2 will help them retain a dense, chewy bite, explains Jenny McCoy, pastry baking arts chef-instructor at the Institute for Culinary Education in New York. Adding more moisture to your dough in the form of extra butter, egg yolks, or brown sugar will make your cookies even softer.

What is the best flour for cookies? ›

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.

What does egg do in cookies? ›

Eggs promote puffiness and spreading in cookies, while also holding the cookie together during baking. The height and texture of the final product is determined by how much egg is incorporated into the batter. Substituting ingredients can make or break a recipe.

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 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.

Why are my cookies splitting? ›

The cracks in crinkle cookies or molasses cookies occur when the top of the cookie dries out before the interior has set. The means that as the cookie expands, it starts to crack the dry surface.

How do you stick broken cookies together? ›

i just put some royal icing where the cookie broke off. i press it together and then set the cookie down and outline it like i normally would. after it's outlined i'll go over that seam and put a layer of icing over it. just for a little more stability once that has a chance to dry for a few minutes.

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