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

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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 sticking together? ›

You can also separate each layer of cookies with wax paper (something we do in our packaging) to keep them from sticking together and falling apart.

How do you keep thumbprint cookies from cracking? ›

If the dough cracks a bit when making the center indentation, roll the ball of dough in your palms a bit longer to warm the dough up more. Don't skip chilling the dough. Chilling the dough will make shaping it into balls easier and hold them together so they won't fall apart when indented. Measure your flour correctly!

Why did my thumbprint cookies spread? ›

Temperature. Dough that is too warm or soft will spread more than dough that is cooler, so if you're working in a very warm kitchen, putting your dough in the fridge for 15 minutes or longer before using it will help prevent spread. Butter that is too warm or soft is also a major culprit.

Why are my thumbprint cookies dry? ›

If your cookie dough is too dry and crumbly, it might not have enough fat. This is a common problem with recipes that use all-purpose flour. To fix this, you can add more fat to the dough. This can be in the form of butter, shortening, or even olive oil.

What ingredient makes cookies stick together? ›

Binding agents are the liquid in the recipe that hold the cookie together. Examples of binding agents are eggs, milk, honey, and fruit juice. Cookies with more eggs will rise more and spread less. If you want a crispier cookie, you can replace a whole egg with just an egg white.

How do you make cookies stick together better? ›

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."

What is another name for thumbprint cookies? ›

Hallongrotta (plural: hallongrottor) is the name of a common Swedish cookie. The name means raspberry cave in Swedish. In the United States they are known as thumbprint cookies, as well as by many other names. Similar cookies sold in Australia are known as jam drops.

How to keep thumbprint cookies from spreading in the oven? ›

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 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!

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.

Why are my thumbprint cookies coming out flat? ›

Oven temperatures are a crucial factor in baking. If your cookies consistently come out flat, you may have selected the wrong baking temperature. If you bake cookies using too much heat, the fats in the dough begin to melt before the other ingredients can cook together and form your cookie's rise.

Can you freeze thumbprints? ›

Yes, you can freeze thumbprint cookies — but it's best to freeze them before filling them with jam. Make and par-bake the dough, then use your thumb to press an indent into each puffed cookie.

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 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.

How do I make sure my cookies keep their shape? ›

Sandwich your dough between two sheets of parchment, roll, then freeze; it makes cut-out cookies a breeze! If you plan to store it for only a few hours or days, there's no need to overwrap the baking sheet; for longer storage, wrap the entire baking sheet tightly with plastic wrap before freezing.

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