Chocolate Rolo Thumbprint Cookies Recipe

Chocolate Rolo Thumbprint Cookies Recipe

While 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.

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Chocolate Crinkle Cookies with a Rolo Surprise

I love hiding edible treasures inside baked goods. The obvious perk is consuming said treats, but I also love seeing others' reactions upon biting into something unexpected. "Oohh, what a good coo....OHHHh! Is that CANDY?! CARAMEL?! WHAT IS THAT?!!" The only thing better than pleasing a friend with a holiday cookie is double pleasing a friend with a holiday cookie. 

This was my first attempt at a crinkle cookie and also my first time baking with black cocoa, which added a delicious touch of richness. If you are unable to find black cocoa, replace it with unsweetened cocoa. The cookies will still make you squeal, I promise.

Here is Day #7 of Twelve Days of Christmas Treats!

In a medium bowl, combine:

2 cups all-purpose flour

3/4 cup unsweetened cocoa powder

1/4 cup black cocoa (substitution: unsweetened cocoa)

2 teaspoons baking powder

1 teaspoon salt

Mix well.

In a large bowl, combine:

10 tablespoons unsalted butter, softened

1 1/2 cups granulated sugar

2 eggs

2 teaspoons vanilla extract

Using a hand-held mixer, mix on medium speed until smooth.

Gradually add the flour mixture and mix until just combined. 

Using your hands, pat the batter into a giant ball and wrap it up in plastic wrap.

Refrigerate for a minimum of 2 hours, or until completely chilled.

While your dough is chilling, unwrap 24 Rolos candies and set them aside.

Preheat your oven to 350 degrees F and line 2 baking sheets with parchment paper.

I turned around to find a gigantic chocolate tower that had been constructed by my youngest helper. Nice, Sammy!

Pour 1 cup of confectioners' sugar into a small bowl and set aside.

Remove the dough from the refrigerator. Scoop out a large spoonful of the dough and flatten it into a disc, using your fingers. Place a Rolo into the center of the disc.

Wrap the dough around it, forming a ball. Smooth out the creases in the dough as much as possible.

Roll the ball in the confectioners' sugar and coat completely. Do this twice! 

Repeat this process with the remainder of the dough and place on the prepared baking sheets.

Bake in the preheated oven for 10 minutes.

Enjoy your weekend (and, um, these cookies)!

Chocolate Crinkle Cookies with a Rolo Surprise

Make people "OOooo!" and "Mmmmm!" as they discover the treasure hiding inside these chocolatey cookies!

Contributed by Megan Porta from pipandebby.com.

Published Dec 7, 2012

Serves: 24

Total time: 1 hr

Chocolate

Ingredients:

  • 2 cups all-purpose flour
  • 3/4 cup unsweetened cocoa powder
  • 1/4 cup black cocoa (substitution: unsweetened cocoa powder)
  • 2 teaspoons baking powder
  • 1 teaspoon salt
  • 10 tablespoons REAL unsalted butter, softened
  • 1 1/2 cups granulated sugar
  • 2 eggs
  • 2 teaspoons vanilla extract
  • 1 cup confectioners’ sugar
  • 24 chocolate-covered caramel candies (such as Rolos), unwrapped
Instructions:
  1. In a medium bowl, combine the flour, cocoa powders, baking powder and salt. Set aside.
  2. Using a hand-held mixer on medium speed, combine the butter, sugar, eggs and vanilla until smooth. Gradually add the flour mixture and mix until just combined. Pat the batter into a giant ball and wrap up in plastic wrap. Refrigerate for a minimum of 2 hours, or until completely chilled.
  3. Preheat oven to 350 degrees F. Line two large baking sheets with parchment paper and set aside. Pour the confectioners’ sugar into a small bowl and set aside.
  4. Remove the chilled dough from the refrigerator. Scoop out a large spoonful of dough and flatten it into a disc using your fingers. Place a chocolate-covered caramel into the center and wrap the dough around it, forming a ball. Smooth out the creases in the dough as much as possible. Roll the ball in the confectioners’ sugar twice, completely covering it both times, and set on the prepared baking sheets. Repeat this process with the remaining dough. Bake in the preheated oven for 10 minutes.

Rolo Stuffed Marshmallow Brownies Recipes

A caramel surprise in every bite! This upgrade to brownies with melted marshmallows is such a tasty treat.

I have started and stopped writing this post about two dozen times, for a thousand different reasons. I won't get into that, but I will tell you that I came up with this brownie recipe during a recent bout of insomnia. I woke up at 3:00 a.m. and started doing my usual stressing/worrying/thinking. I decided to turn my thoughts into something productive, so I started thinking about food! And what better food to ponder than brownies?

I have been loving the "stuffed" treats lately, Chocolate Crinkle Cookies with a Rolo Surprise and Double Chocolate Cookies with a Peppermint Surprise! SOOO (after some pondering) I came up with the idea of brownies stuffed with one of my all-time favorite candies, Rolos. I needed just a little something extra, and roasted marshmallows seemed like the perfect thing to throw on the top.

Most treats that I make end up being shared with my coworkers. These brownies did not get shared with my coworkers. My husband and I ate the ENTIRE batch by ourselves. Every last crumb. I can't even tell you how sinfully delicious they were. 

These are well worth being awake in the middle of the night!