Chocolate Chocolate Chip Sandwich Cookies with Cinnamon Buttercream

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

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.

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

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.

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

Holy cow. It’s a chocolate chip cookie. But it’s also a chocolate chocolate chip cookie. With these big, dark Ghirardelli 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.

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

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 love how the Ghirardelli chips 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.

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

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 with Cinnamon Buttercream // The Live-In Kitchen

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Chocolate Chocolate Chip Sandwich Cookies with Cinnamon Buttercream
  • For the 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 plus 2 tablespoons unsweetened cocoa powder
  • ½ teaspoon baking soda
  • ¼ teaspoon salt
  • 1¼ cups Ghirardelli 60% cacao bittersweet chocolate baking chips
  • For the Buttercream:
  • ½ cup (1 stick) unsalted butter, softened
  • ½ teaspoon pure vanilla extract
  • 2 teaspoons cinnamon
  • 1¼ cups powdered sugar, sifted
  • 1½ tablespoons heavy cream
  • A few drops of natural food coloring (optional)
  1. To make the cookies, heat the oven to 350ºF. Line a baking sheet with parchment paper or a Silpat.
  2. Place cold butter in a small bowl and microwave in 4 second bursts until it is slightly melted.
  3. 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.
  4. 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.
  5. 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.
  6. 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.

I was selected for this opportunity as a member of Clever Girls Collective and the content and opinions expressed here are all my own.


  1. Joy says

    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.

    • says

      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!

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