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    Home » Dessert Recipes » Cookie Recipes

    Chocolate Chocolate Chip Cinnamon Sandwich Cookies

    Lindsay Moe

    798 shares
    several chocolate sandwich cookies with pink buttercream on a wood table
    Jump to Recipe

    My husband and I don’t really do Valentine’s day.

    We prefer to make an effort each day to make sure each person feels and knows they are loved. We voice our needs and make an effort to meet each other’s expectations in ways like taking out the trash, cleaning up the kitchen, or cuddling on the couch watching Girls (oh, Hannah…).

    We take the cultural pressure off this one day in February that is supposed to be over the top and extravagant and just allow each other to be loved year round. I don’t know about you, but if I get my hopes up about something (fancy dinner, a dozen roses) chances are the reality will never match up to my imagination. Such is Valentine’s day.

    a stack of chocolate sandwich cookies

    One way I never hesitate to go over the top is with food. I will take any excuse to consume something rich, decadent, and extravagant. Let’s meet my friend the chocolate chocolate chip sandwich cookie with cinnamon buttercream.

    Holy cow. It’s a chocolate chip cookie. But it’s also a chocolate chocolate chip cookie.

    With these big, dark chocolate chips (disks, if you really ask me) they come out of the oven so soft and gooey that you wonder if they’ll even make it to their destined sandwich form. Sandwiching them together automatically makes it acceptable to eat two, because you know you were going to anyways.

    Believe me, they are perfection right there.

    several chocolate chocolate chip sandwich cookies

    The hardest part is waiting. The cookies need to cool completely before you can even begin to think about sandwiching them together.

    The puddles of melted chocolate being embraced by sweet chocolate dough make this a fragile cookie to handle before it is completely cooled. I used Ghirardelli chocolate chips, and I love that they are larger than other chocolate chips, creating a greater impact of chocolate flavor.

    The chips have a flavor and texture that are high quality while still being affordable and readily available at my local grocery store.

    cinnamon buttercream in a small bowl with a small knife

    While you’re waiting for the cookies to cool you can work on your buttercream. The cinnamon brings a subtle, warming flavor to the sweetness of the butter and sugar.

    I’m not a huge fan of the color pink, but I’m completely obsessed with this dusty rose color. It looks like sweet little baby lips, ready to kiss you.

    This is a delightfully small batch of cookies, just right for loving your family or co-workers without having too many leftovers lying around threatening your thighs. If it’s just you and your sweetie you’ll have plenty of decadence with enough sandwich cookies to last you the rest of the week. All food holidays should last a week anyways.

    chocolate chocolate chip sandwich cookies on a wood table with a bowl of cinnamon buttercream filling

    If you make this recipe, be sure to rate it, leave a comment, or tag #theliveinkitchen on Instagram!

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    Recipe

    Chocolate Chocolate Chip Sandwich Cookies with Cinnamon Buttercream // The Live-In Kitchen

    Chocolate Chocolate Chip Sandwich Cookies with Cinnamon Buttercream

    This rich chocolate cookies have crisp edges, soft centers, and cinnamon buttercream slathered in the middle!
    5 from 2 votes
    Print Pin Rate SaveSaved!
    Prep Time: 1 hour hour
    Cook Time: 8 minutes minutes
    Total Time: 1 hour hour 8 minutes minutes
    Servings: 8
    Calories: 604kcal
    Author: Lindsay Moe

    Ingredients

    Cookies

    • 7 tablespoons cold unsalted butter
    • 1 cup granulated sugar
    • 1 teaspoon pure vanilla extract
    • 1 large egg
    • 1 cup unbleached all-purpose flour
    • ¼ cup unsweetened cocoa powder
    • 2 tablespoons unsweetened cocoa powder
    • ½ teaspoon baking soda
    • ¼ teaspoon salt
    • 1 ¼ cups Ghirardelli 60% cacao bittersweet chocolate baking chips

    Buttercream

    • ½ cup (1 stick) unsalted butter, softened
    • ½ teaspoon pure vanilla extract
    • 2 teaspoons cinnamon
    • 1 ¼ cups powdered sugar, , sifted
    • 1 ½ tablespoons heavy cream
    • A few drops of natural food coloring, (optional)

    Instructions

    • To make the cookies, heat the oven to 350ºF. Line a baking sheet with parchment paper or a Silpat.
    • Place cold butter in a small bowl and microwave in 4 second bursts until it is slightly melted.
    • In a stand mixer fitted with the paddle attachment, beat butter on medium speed until light. Add the sugar and beat until light and fluffy, about one minute. Add the vanilla and egg and beat just until incorporated. Add flour, cocoa, soda, and salt, and pulse to prevent the dry ingredients from coming out the sides. Once the mixture starts to come together, mix on low speed just until fully incorporated. Fold in chocolate chips with a rubber spatula.
    • Roll golf ball sized mounds of dough between your hands and place at least two inches apart on the prepared baking sheet. Bake 8 minutes. Cookies will still be very soft but should no longer appear wet on top. Allow the cookies to cool 10 minutes on the baking sheet before very carefully removing to a cooling rack to cool completely. You want the cookies to be completely cool before frosting. You can place them carefully in the refrigerator to speed up this process.
    • To make the buttercream, beat butter in the bowl of a stand mixer fitted with the paddle attachment until light. Mix in vanilla and cinnamon. Add powdered sugar and heavy cream and mix until smooth. You can adjust the consistency of the frosting by adding more powdered sugar to stiffen or more heavy cream to loosen it up. If desired, add a few drops of natural red food coloring to achieve the pink color.
    • Spread a generous amount of frosting on the bottom of one cookie and gently press another against it to create a sandwich. Store cookies in an airtight container in the refrigerator for 3-5 days. Makes 8 sandwich cookies.

    Nutrition

    Calories: 604kcal | Carbohydrates: 72g | Protein: 5g | Fat: 34g | Saturated Fat: 20g | Cholesterol: 82mg | Sodium: 157mg | Potassium: 239mg | Fiber: 4g | Sugar: 53g | Vitamin A: 745IU | Calcium: 41mg | Iron: 3.1mg
    Tried this recipe?Mention @theliveinkitchen or tag #theliveinkitchen!

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    Reader Interactions

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    1. Kendra says

      February 05, 2014 at 9:12 am

      Another mouth watering cookie! They look like the perfect match for a glass of milk.

      Reply
    2. Alice // Hip Foodie Mom says

      February 06, 2014 at 9:29 am

      I love this! Holy cow! This is taking a chocolate chocolate chip cookie to a whole different level!!! and I also love the Ghirardelli bittersweet chocolate chips!

      Reply
    3. Alice // Hip Foodie Mom says

      February 06, 2014 at 9:31 am

      hey, I just realized you are in WI too!! I just moved to Madison this past November!

      Reply
      • Lindsay Moe says

        February 06, 2014 at 1:41 pm

        Fun! Always good to know another semi-local blogger! I hope you’re staying warm.

        Reply
    4. Dina says

      February 08, 2014 at 9:00 am

      they look yummy!

      Reply
    5. Shikha | Shikha la mode says

      February 11, 2014 at 2:52 pm

      i love the look of those cookies – that’s so cool that Ghirardelli sponsored you, how did that happen?

      Reply
    6. Joy says

      February 16, 2014 at 8:38 pm

      I made these last night and they were/are a-m-a-z-i-n-g. It’s one of those recipes that I’ll actually print out just in case the webpage mysteriously disappears– it’s that good. I wouldn’t be able to handle losing this one. I’m wondering, though, how yours came out so flat and perfect for sandwiching? Mine had a lot more volume (not as conducive to sandwiching). I used Ghirardelli milk chocolate chips because I’m a milk chocolate kind of girl, but I can’t imagine that would make a difference. Any thoughts? Did you do anything to flatten them? We ended up eating them more like open-face sandwiches (still incredible, but…). Also, did you use all of the buttercream with just one batch of the cookies? Seems like a bit too much buttercream to me (I’m inclined to halve the recipe next time), but maybe if I had properly sandwiched them…? Anyway, thanks SO much for sharing this one! And by the way, I’m totally with you about Valentine’s Day.

      Reply
      • Lindsay Moe says

        February 17, 2014 at 7:45 pm

        I’m so glad you liked them Joy! I have a couple ideas of why your cookies turned out a little thicker. One could be you mixed the ingredients longer, whipping more air into the batter. It is also possible that over baking the cookies would make them thicker. The finished cookie should still be very soft when they come out of the oven and deflate a bit as it cools. When you ball up the dough you can also flatten it with the palm of your hand a bit to encourage it to spread out. I did use all of the buttercream for one batch of cookies, minus maybe a spoonful that found its’ way into my mouth (shhh…). But obviously, I love buttercream and may have been ok with a thicker middle!

        Reply

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    lindsay moe in a kitchen with glasses on shelves behind her

    Hi, I'm Lindsay! I've been creating easily customizable vegetarian recipes since 2011. I love the outdoors, brownies, and brand new books. I live and work in La Crosse, Wisconsin and founded Wild Flour Media to expand on my love for food photography and videography to my community and beyond.

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    798 shares