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? ›

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? ›

One way is to add in some extra fat, such as more butter or even an extra egg yolk (which contains fat) — this will make the dough easy to work with again. Another way to fix the problem is to add in a bit of extra liquid, such as milk or water, which will help get the dough back to the consistency it needs to be.

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 makes cookies too 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. The cookie should be baked only until the edges are slightly golden and the top looks a little wrinkled.

Should you fill Thumbprint Cookies before or after baking? ›

Thumbprint cookies should be filled before baking. This gives the jam time in the oven to firm up and set a little.

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.

How do you make cookies thick and not flat? ›

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 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.

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.

What happens if you use more brown sugar than granulated sugar in a cookie recipe? ›

So, if your recipe calls for one cup of white sugar, swap one cup of brown sugar. The sweetness level will be the same, but the brown sugar may change the texture of your baked goods. You'll likely notice a more robust flavor, and the finished baked goods' color may also be darker.

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.

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).

Why won't my cookies stay together? ›

If you reduce the amount of butter or oil in a recipe, your cookies won't spread as much. If you add too much flour, your cookies won't spread as much. If your cookies have more brown sugar than white sugar, they won't spread as much. It's a careful balance.

How do you stick broken cookies together? ›

Use that royal icing as. glue and let it dry.

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

To help cookies keep their shape, freeze them! I freeze each batch of cut-out cookies for 5 to 10 minutes before baking. They rise just slightly higher and keep their shape better. This really helps when using an intricate cookie cutter, but I do this even when baking circles.

How do you keep cookies from sticking together? ›

Store cookies in layers

The last thing you want is for your cookies to stick together! To prevent sticking when you store your cookies, arrange them in a single layer and add a piece of parchment paper or waxed paper between layers. (Here's why you should bake cookies on parchment paper, too!)

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