Double Dark Chocolate Chip Shortbread Cookies

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double dark chocolate chip shortbread cookies-3021-July 28, 2017-2

Double Dark Chocolate Chip Shortbread Cookies ~ they melt in your mouth with an explosion of deep rich chocolate that’ll make your eyelids flutter… to call it a cookie is to completely miss the point.

VINTAGE VIEW ~ these Double Dark Chocolate Chip Shortbread Cookies are from TVFGI archives, way back from the winter of 2011. As part of a new series on the blog I’m reviving some of my favorite recipes that you may have missed over the years. I’m refreshing the photos and commentary but the recipe remains the same, the only change I made was to double it ~ these unusual cookies are a special treat!

These are not your every day chocolate chip cookies, and I don’t want anybody here under false pretenses. There really is nothing else like these cookies ~ if you have not yet made this recipe then I can safely say you haven’t tasted anything like this before…it combines the buttery mouthfeel of shortbread with deep rich chocolate flavor…I used extra dark cocoa powder and dark chocolate chips, so this is about the richest chocolate you can bite into short of a truffle. Seriously.

The flavor is bittersweet, which is a very different, more intense, more sophisticated chocolate experience, and if you’re not expecting it you might be thrown for a loop. The mouthfeel of the shortbread is different, too, it’s crumbly but not at all dry, and sticks to the roof of your mouth. Are you up for this? –– then proceed, if not, turn back now!

Yes, the inside of that cookie is so dark it’s basically black. In fact the cookie is so dark that it makes my bittersweet chocolate chips look like milk chocolate in comparison. That’s because I used Hershey’s Special Dark cocoa powder. It’s a specially formulated Dutch processed cocoa which, among other things, has a richer color and smoother flavor compared to regular cocoa powder. It’s what gives Oreo cookies their deep color.

Because of all that Dutch process cocoa, I warn you making these cookies is messy ~ messy like making mud pies messy…

The dough stains your hands and the cocoa powder flies everywhere. But it’s a small price to pay for transcendent chocolate cookies. At least in my book. You can roll this dough into a log and slice and bake it, or roll it out and cut out your cookies, both ways work, but either way it needs to be chilled for several hours before slicing and baking since it’s a butter rich dough.

Be sure to check out my other shortbread cookies, I’ve done a killer Peanut Butter Chocolate Chip version, a classic Chocolate Chip Shortbread, and an Dark Espresso Chocolate Chip, too!

I used Hershey’s Special Dark Cocoa powder for these cookies—I love it but it can sometimes be hard to find in stores, so I usually buy it in bulk on Amazon, here.

*The View from Great Island is a participant in the Amazon Services LLC Associates Program ~ Your cost is the same, but I earn a small commission from Amazon which helps keep tvfgi operating.

Double Dark Chocolate Shortbread Cookies
Rate this recipe
25 ratings

Category: cookie, dessert

Cuisine: American

Yield: 18 cookies

Double Dark Chocolate Shortbread Cookies

Dark and decadent chocolate chip shortbread cookies!


  • 2 sticks (1 cup) unsalted butter, at room temperature (this is important)
  • 1/2 cup confectioner's sugar, sifted
  • 1/2 cup dark cocoa powder, sifted (I use Hershey's Special Dark)
  • 2 teaspoons vanilla
  • 1 1/2 cups all-purpose flour
  • 1 cup dark chocolate chips


  1. Cream the butter, cocoa powder and sugar together until completely combined and smooth. Add in the vanilla. if using a stand mixer, be sure to scrape down the sides of the bowl.
  2. Mix in the flour, making sure to get it thoroughly blended, but don't over mix.
  3. Fold in the chocolate chips and turn the dough out onto a board dusted with cocoa powder. The dough will be sticky.
  4. For roll and cut cookies, form into an 8 inch disk (like you would do for pie dough.) Wrap in plastic and refrigerate for at least 3 hours or until firm enough to roll out. You can also freeze the dough for later use.
  5. Preheat oven to 325F
  6. Roll the disk out to 1/3 inch thickness and cut cookies with a 2 1/2 inch round cookie cutter. Use cocoa powder liberally to prevent sticking to the surface and to your rolling pin. Place the cookies on a parchment lined baking sheet and bake for 12-15 minutes. The cookies will still be soft, but will firm up as they cool. Cool them on the baking sheet for 10 minutes, then carefully transfer them to a cooling rack.
  7. For slice and bake cookies, form a 10" log. Wrap in plastic wrap, smoothing the dough as you wrap it, and twist the ends to secure. Refrigerate for at least 3 hours until firm enough to slice. You can also freeze the dough for later use.
  8. Slice the log into 1/3" slices with a sharp knife. If some of the chips fall out of place, or the dough crumbles as you slice, reform it with your hands. Place the cookies on a parchment lined baking sheet and bake for 12-15 minutes. The cookies will still be soft, but will firm up as they cool. Cool them on the baking sheet for 10 minutes, then carefully transfer them to a cooling rack.
  9. Note: Because of the chocolate chips these cookies will not be perfectly uniform or smooth.

Make it your own ~

  • You might try substituting walnuts for the chocolate chips.
  • There’s no reason why you can’t use any cocoa powder or type of chocolate chip you like in these cookies, the color and flavor will vary, but they will still be delicious.



Don’t forget to pin these Double Dark Chocolate Chip Shortbread Cookies!

Double Dark Chocolate Chip Shortbread Cookies ~ they melt in your mouth with an explosion of deep rich chocolate that'll make your eyelids flutter... to call it a cookie is to completely miss the point. #COOKIES #CHOCOLATE #CHOCOLATECHIPCOOKIES #SHORTBREAD #BESTCHOCOLATECOOKIES #DARKCHOCOLATE #DARKCHOCOLATECOOKIES #HERSHEYSSPECIALDARK #DARKCHOCOLATECHIPCOOKIES #HOLIDAYS #CHRISTMASCOOKIES #SLICEANDBAKE

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  • Reply
    December 8, 2018 at 5:25 am

    These look delicious! They look like they held their shape well and was wondering if they might be good for cutout cookies? Do you think they would hold their shape if using a cookie cutter?

    • Reply
      December 8, 2018 at 7:54 am

      They would hold their shape but I would use a plain round cutter, intricate shapes won’t work. And the chocolate chips can be an issue, getting in the way of the edge of the cutter, you might consider using small chips.

  • Reply
    October 14, 2018 at 12:18 am

    I made these tonight and they came out perfectly! Exactly the richness I was looking for and much less buttery tasting in comparison to plain shortbreads (#Chocoholic!). I added chocolate chunks for added texture and next time will try adding macadamia nuts. These have become a new Fall/Winter baking season must have! Appreciate the recipe!!!!

    • Reply
      October 14, 2018 at 9:32 am

      Thanks Jessica ~ I think these cookies are too intense for some, but for us true chocoholics they’re nirvana!

  • Reply
    My Favorite Chocolate Chip Oatmeal Cookies | Wishes and Dishes
    June 25, 2018 at 9:05 pm

    […] exciting, try my Oreo Stuffed Chocolate Chip Cookies. They are so fun! You will also love these Double Dark Chocolate Chip Shortbread Cookies from my friend Susan. […]

  • Reply
    Shirley Sanderson
    March 11, 2018 at 8:38 pm

    This recipe makes a tasty cookie, but they are super crumbly. I’ve never made cookies before that turned out this crumbly. I think the recipe needs some tweaks to fix this problem.

    • Reply
      October 14, 2018 at 9:33 am

      It’s possible that the dough didn’t get completely combined, meaning the butter and flour need to be really blended together.. Also some butters have less moisture than others, so a tiny splash of milk can help the dough come together. Hope this helps Shirley.

  • Reply
    February 18, 2018 at 1:47 pm

    I made these last night. While they were in the oven I read the comments. The issue with them being crumbly is that these need to go from ove to cool down to refrigerator and then freezer as quickly as possible with the least amount of handling. They are a butter cookie, and as such, need to be served cold. Especially this recipe. They handle really well after cold, where as they just desintigrate if handled warm.

    Overall, this is a grand cookie. I can’t eat just one. I was looking for a cookie that would pair well with several varieties of wine. Your cookie is a winner! Thank you!

    • Reply
      February 18, 2018 at 1:48 pm

      Thanks for the detailed feedback Jynja, it’s helpful :)

      • Reply
        February 18, 2018 at 1:49 pm

        And I’d never thought about pairing them with wine, interesting!

  • Reply
    January 17, 2018 at 4:57 pm

    Hi there! I made these last night and they are DELICIOUS- not too sweet, deep dark chocolate flavor, just incredible. The only thing I felt was off was the texture- I love a harder shortbread cookie and these turned out pretty soft, even though I baked them for a little longer than directed. They were perfect otherwise, nice and crumbly. Are these normally just a softer cookie? My oven is not super consistent so it could have just been that too.

    • Reply
      January 17, 2018 at 5:05 pm

      I prefer my shortbread soft, so this recipe is probably skewed a little on the soft side, and the presence of chocolate chips makes them seem softer, too. I suggest cutting the dough a little thinner and baking a little longer for more of a crunch! But if your oven is not consistent, I would tackle that problem first.

      • Reply
        January 17, 2018 at 5:12 pm

        Thanks for the reply! I’ll try that next time. Even soft, though, these aren’t making it out of my house- delicious with a cup of coffee!

  • Reply
    December 18, 2017 at 7:58 am

    Making these for a cookie exchange and I’m using Ghirardelli Peppermint Chunks instead of chocolate chips. So excited!

    • Reply
      December 18, 2017 at 7:59 am

      Mmmmmm, let me know how it tastes!

  • Reply
    November 28, 2017 at 10:50 pm

    I made these today, swapping out all vanilla for a mixture of orange and vanilla extracts. Yummo! Set them out, turned around, and they were gone! Thanks for the delicious addition to my holiday recipes/cookie exchange.

    • Reply
      November 29, 2017 at 7:14 am

      I love chocolate and orange together, thanks for the tip!

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