Chocolate Chip Cinnamon Roll Cookies

Chocolate Chip Cinnamon Roll Cookies from BakingdomI have a confession to make.

I made these cookies while the Hubster was away. That means no sharing, and no leftovers going into his fellow Coasties with him.

That means just me and these cookies. Alone. For a whole week.

They had some strange power over me. I was constantly thinking of them at all hours. I kept walking to the kitchen, ‘just for one bite’. By the end of the week, I found myself lurking in corners, furtively nibbling cookies where the healthy food couldn’t see me. I didn’t need the apples judging me, thankyouverymuch.

If there’s such a thing as a cookie vampire, I’m pretty sure these are the cause.

So basically, what I’m saying is, make these cookies. They’re amazing.

Cinnamon Roll Cookies FillingThe cookies are inspired by my Cinnarookies recipe, and they are super easy to make, and they don’t take much time, but there is some chilling required after mixing. Once the dough is chilled, you’ll shape it. On a large piece of plastic wrap, pat half of the dough into a rectangle about nine inches by twelve inches, and about half an inch thick. Next, you’ll spread some butter all the way to the edges and sprinkle a chocolate brown sugar mixture evenly over the buttered dough, pressing it into the dough. I also decided to sprinkle some extra chocolate chips on mine, but you don’t have to. You should. But you don’t have to. I guess.

Roll Cinnamon Roll Cookie DoughOnce the filling ingredients are all added, use the plastic wrap to tightly roll the dough into a log. Seal the plastic wrap around the cookie dough and place the log in the freezer for 30 minutes or the refrigerator for at least an hour. Repeat with the remaining half of the dough and filling ingredients. I have found that using the plastic wrap to help roll the dough, really makes it cleaner and faster.

Slice Cinnamon Roll CookiesAfter the rolled dough is chilled, you’ll slice it into half inch slices (about 24). Now, it’s just time to bake. 🙂

Easy Chocolate Chip Cinnamon Roll Cookies from BakingdomThese will spread a bit during baking, but not much, so you can fit these about two-inches apart on the baking sheet.

these cookies are so good, they have plenty of flavor straight out of the oven…sweet and spicy with a deep chocolate addition…but if you want even more goodness…

Chocolate Iced Cinnamon Roll Cookies from Bakingdom…you can drizzle them with a milk chocolate icing.

Delicious icing is delicious.

It’s also ridiculously easy, so there’s really no reason not to dress your cookies up in a pretty drizzle.

Chocolate-glazed Chocolate Chip Cinnamon Roll CookiesI made the mistake of making these cookies while the Hubster was away, so not only was he not here to share these with me, but that also meant that he didn’t take any to work. So wish I could say the cookies had a fighting chance, but the truth is, I ate them all. All of them. The end.

I wouldn’t recommend making these if you don’t have anyone to share them with. Unless you want to become a real like Cookie Monster.


Chocolate Chip Cinnarookies
Makes about 4 dozen cookies


1 cup (2 sticks) unsalted butter, softened
1/2 cup brown sugar
1/2 cup sugar
2 eggs
1 teaspoon vanilla
2 teaspoons cinnamon
3 cups flour
2 teaspoons baking powder
1 teaspoon salt
1/2 cup semi-sweet mini chocolate chips

1/4 cup (1/2 stick) unsalted butter, very soft
1/4, plus 2 tablespoons packed brown sugar
1 tablespoon cocoa powder
2 teaspoons cinnamon
1 to 2 tablespoons more mini chocolate chips, optional

2 cups confectioners’ sugar
2 tablespoons melted butter
2 tablespoons cocoa powder
2 teaspoons vanilla
2-4 tablespoons milk

To make the cookies: In a medium bowl, combine the flour, cinnamon, baking powder, and salt; set aside.

In a large bowl, or the bowl of a standing mixer, cream the butter and sugars together until light and fluffy. Add the eggs one at a time, and beat until just combined. Scrape the sides of the bowl, then add half of the flour mixture and mix until just combined. Add the remaining flour mixture and beat until thoroughly combined, scraping the bowl as needed. Stir in the chocolate chips until evenly distributed. Scrape the dough into a ball in the center of the bowl, cover with plastic wrap, and chill in the freezer for 30 minutes, or the refrigerator for at least an hour.

To make the filling: In a medium bowl, combine the brown sugar, cocoa powder, and cinnamon; set aside. Once the dough is chilled, divide it into two equal halves. Place one half back in the bowl and put it back in the refrigerator for now. On a large piece of plastic wrap, pat the first half of the dough into a rectangle about 9-inches by 12-inches, and about 1/2-inch thick. Place half of the filling butter on the dough and spread it all the way to the edges. Sprinkle half of the brown sugar mixture evenly over the buttered dough and press the sugar into the dough. If using, sprinkle a tablespoon or so of mini chocolate chips evenly over the dough. Use the plastic wrap to tightly roll the dough into a log, wrap the dough in the plastic wrap. Place in the freezer for 30 minutes, or the refrigerator for at least an hour. Repeat with the remaining half of the dough and filling ingredients.

Preheat the oven to 350 degrees. Line a baking sheet with Silpat mats or parchment paper.

After the dough has chilled again, slice into half inch slices (about 24 per batch of dough). Place on the prepared baking sheets and bake for 10 to 12 minutes. Transfer to a wire cooling rack and allow to cool completely before icing.

To make the icing: In a medium bowl, combine the butter and cocoa powder. Add the confectioners’ sugar and vanilla and whisk until it just comes together. Next, add the milk, one tablespoon at a time until the desired consistency is reached. It should be thin enough to drizzle, but thicker than a glaze.

With the cookies on a wire cooling rack set over parchment paper, drizzle the icing over the them with your whisk. Allow the cookies to set up before stacking or storing.

Recipe by Darla

Delicious Cinnamon Roll Cookies from Bakingdom

Leave a comment


  1. M says

    These look even more delicious than the cinnamon roll cookies by themselves!

    I was looking for recipes for a baking contest at work which was the first time I made the ones for the original recipe. I hate sugar cookies so I was skeptical but they turned out so delicious that I won the contest and my managers requested I make them again because not everyone got to try them.

    And now one manager is hounding me to give up the link to the recipe, I’m just not sure I am willing to give up that card up my sleeve just yet!

  2. Laura says

    Totally not judging you for eating every. last. bite. Can’t wait to try these! Oh and chocolate brown sugar mixture? Why have I never thought about that?!

  3. Julie says

    I made these tonight, and they were a HUGE hit!!!! On to cookie portion, however, the recipe doesn’t state when to add the vanilla in the cookie dough. I added after the second egg.
    Cooking time for me, in Dallas, TX, was about 14 minutes, and they could have probably used another 2 minutes.
    They were fantastic. Darla, your recipes never disappoint. Many thanks.

  4. says

    You make that rolling look so easy, but I’m pretty sure mine would be a mess! I love the originality of this recipe. I bake for a group I go to at school once a week, and I think these might just be the next thing I make!

  5. Crystal Tejada says

    These were delicious and a hit with my recipe testers at my internship lol I used Dutch Cocoa because I ran out of cocoa powder but I will make them with regular cocoa powder this weekend! I also baked them for 12 min and wondered if they should bake longer, I left them on the cookie sheet for a few minutes before transferring to the cooling rack, I also forgot the vanilla cuz it wasn’t listed in the instructions so maybe you should consider adding it! Thanks for the recipe!!!!

  6. Erin Maree says

    The dough is chilling as I type this! I was tossing up whether to make these or not but when I asked my sister if she wanted cookies and she said ok (she needs cookies to survive haha!) my mind was made!
    I only have dark normal choc chips (can’t seem to find minis any where over here! And dark chocolate always makes things a bit richer so we always have that 🙂 ) but the dough looks good and came together really easier despite me not using a mix master (just used a wooden spoon and elbow grease) as my mum was/is having a sleep and didn’t want to make so much noise. Looking at trying them of course my sister will probably eat them all haha

  7. Miriam says

    I’m making these for a Halloween party this weekend as they look a little spooky (almost a little nightmare before christmas’y). I have yet to find a recipe of yours that doesn’t’ turn out to be an amazing hit. 🙂