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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)!

Printable recipe: Chocolate crinkle cookies with a Rolo surprise

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Reader Comments (11)

What a great idea to stick a Rolo in the middle! I just made plain crinkle cookies and now I wish I had seen this first!

wow how tempted!

12.7.2012 | Unregistered CommenterQQ

what a wonderful idea....I am going to try this one soon.

12.8.2012 | Unregistered Commenterila

I've made these before, and maybe you can shed some light on this problem: the cookies were fantastic warm, but as soon as they cooled, the Rolo in the middle got all hard. Like harder than it was before baking it. Did this happen to you?

12.10.2012 | Unregistered CommenterSarah O.

Hi Sarah,
If you bake it for too long, you can harden the caramel in the Rolo. I didn't have that problem with these cookies. Good luck!

12.10.2012 | Registered CommenterMegan Porta

I'm finally chiming in to tell you that these were my favorite cookies we made this year! I paid close attention to baking them for only 10 minutes as well and they came out amazing, they maintained the caramel gooeyness thru out the week. Loved-Loved these! In fact, I grabbed another bag of rolo's that were marked for clearance to make more for valentines.

01.1.2013 | Unregistered CommenterPat

I was just wondering if you could tell me what I did wrong. My cookie dough doesn't look like the consistency of yours. My dough is sticky and I followed the recipe to the T. Thanks..!!

02.10.2013 | Unregistered CommenterDarla Lynne

I made these cookies on Tuesday, and they went amazingly. I normally have to convert dreaded/infuriating cups recipes to grams (English fan here), but my scales broke and my new cheap replacements are so inaccurate, so I used online conversion to use tablespoons. My dough was very very sticky, so I added more and more flour till the consistency seemed more like what your picture showed of the dough.

My fan oven is also very inaccurate, the top tray cookies were in 3 minutes longer than the bottom tray, the bottom tray cookies were perfect after 10 minutes, the top tray came out a little undone so had to stay in a little longer.

Tastiest cookies ever! I brought some into work (I work in a kitchen and am starting my NVQ in professional cookery soon) and they were too rich for the chefs, but two barstaff adored them and asked for the recipe (they're both on strict diets according to their wives, but at work the diets slack a little bit :P).

Thank you so much. I also indulged in making cookie dough and sandwiching this between two of these cookies - pure unadulterated bliss, that alongside vanilla chai tea, sat with a facemask on and my feet in a footspa on my day off made a wonderful day. Thank you!

05.17.2013 | Unregistered CommenterLiadháin

Hi. These look amazing and I would love to try them this weekend. I can't seem to find a "print" icon on the webpage to print out the recipe. Is there one and I just can't see it? Thanks. Kim

12.4.2013 | Unregistered CommenterKim

Hi Kim! There is a link for a printable recipe just below the last photo. Let me know if you can't see it and I can email one to you!

12.5.2013 | Registered CommenterMegan Porta

Wow! Chocolate overload! Delicious, but have a glass of milk handy!

12.15.2013 | Unregistered CommenterPhyllis

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