These orange chocolate shortbread cookies are a takeoff from the classic thumbprint cookies I used to make with my gram.
These cookies are some of my favorites to make at Christmastime. I wish I had a better name for them, but I went with the very straight “Orange Chocolate Shortbread Cookies.”
I first made these for the cookie sale at the animal shelter where I volunteer every winter. I wanted something unique that would draw people to it and still include comforting flavors.
As I thought about it, I realized that orange is always one of my favorite holiday flavors, and chocolate just seems to go naturally with it. (Of course, my husband thinks chocolate goes naturally with everything – and who am I to contradict him?)
One of my favorite treats is the chocolate oranges that Kraft makes. I’ve always looked for a recipe that incorporates those flavors, but I never managed to find a recipe for a cookie with orange flavoring, so I decided this challenge would fit the bill.
I based it very loosely on a shortbread recipe since that was the cookie that seemed to hold its shape the best. And if you love shortbread, definitely try my chocolate dipped peppermint shortbread. So. Good.
This orange chocolate shortbread isn’t dry or crumbly like so many I’ve seen. It’s perfect for the filling and doesn’t overwhelm the citrus flavor with sweetness either.
Of all the variations I’ve tried, this seems to have won the most fans. That and they’re surprisingly easy to make (and very forgiving, too)!

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How to Make Orange Chocolate Shortbread Cookies
Make the filling first and let come to room temperature before starting the cookies.
For the Filling:
Scald cream in a heavy saucepan. Remove from heat and add chocolate, stirring until fully melted.
Add Grand Marnier and stir. Slowly add powdered sugar and stir until combined.
Set aside until cookies are cooled.
For the Cookies:
Preheat oven to 325 degrees. Cream the room-temperature butter and brown sugar. Add the orange zest and orange juice, then the egg. Mix until well combined.
Add the baking soda and salt, then mix again. Slowly add the flour and stir until fully combined. The dough should be fairly stiff. Roll small amounts of the dough into balls and place them onto a greased cookie sheet.
Using a clean finger or the back of an iced tea spoon, make a large, deep divot into each ball (the bigger the divot, the more filling fits!). Bake each set of cookies for 11-13 minutes until firm. These cookies do not crack when done. As soon as each batch comes out of the oven, carefully use the spoon to reaffirm the divot.
Let cookies cool for 10 minutes. Once cookies are cool to the touch, use the iced tea spoon to carefully fill each divot with thickened chocolate filling. Let cookies sit for 2+ hours for filling to set.
This makes approximately 4 dozen cookies.

Orange Chocolate Shortbread Cookies
Ingredients
For the Cookies:
- 10 tablespoons unsalted butter room temperature
- 3/4 cup brown sugar
- 1 orange zest
- 1 orange juice
- 1 egg
- 3/4 teaspoon baking soda
- 1/4 teaspoon salt
- 3 cups flour
For the Filling:
- 1/2 cup cream
- 8 ounces bittersweet chocolate
- 2 tablespoons Grand Marnier
- 1/2 cup powdered sugar
Instructions
For the Filling:
- Make the filling first and let come to room temperature before starting the cookies.
- Scald cream in a heavy saucepan. Remove from heat and add chocolate, stirring until fully melted.1/2 cup cream, 8 ounces bittersweet chocolate
- Add Grand Marnier and stir. Slowly add powdered sugar and stir until combined.2 tablespoons Grand Marnier, 1/2 cup powdered sugar
- Set aside until cookies are cooled.
For the Cookies:
- Preheat oven to 325 degrees. Cream the room temperature butter and brown sugar. Add the orange zest and orange juice, then the egg. Mix until well combined.10 tablespoons unsalted butter, 3/4 cup brown sugar, 1 orange zest, 1 orange juice, 1 egg
- Add the baking soda and salt, then mix again. Slowly add the flour and stir until fully combined. The dough should be fairly stiff. Roll small amounts of the dough into balls and place onto greased cookie sheet.3/4 teaspoon baking soda, 1/4 teaspoon salt, 3 cups flour
- Using a clean finger or back of an ice tea spoon, make a large, deep divot into each ball. Bake each set of cookies 11-13 minutes until firm. As soon as each batch comes out of the oven, carefully use the spoon to reaffirm the divot.
- Let cookies cool for 10 minutes. Once cookies are cool to the touch, use the ice tea spoon to carefully fill each divot with thickened chocolate filling. Let cookies sit for 2+ hour for filling to set.
- This makes approximately 4 dozen cookies. Serve and enjoy!
Notes
- Feel free to adjust the size of the divot based on your preference. A larger divot will hold more chocolate filling.
- Since these cookies won’t crack during baking, you can use the iced tea spoon to gently deepen the divot in the center of each cookie after they come out of the oven. This will create a nice pocket for the chocolate filling.
- For more tips and tricks, be sure to read the full article above.
Nutrition
This site uses an online source to provide nutrition estimates as a courtesy. If you need exact values, please calculate yourself.
Make sure to pin this orange chocolate shortbread cookie recipe to make again!

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Angela – Can’t wait to hear your verdict once you make them. Still waiting on the rest of your insight… promises, promises! 😉
Trashalout – Welcome! And you’re welcome! If you do try them out, definitely let me know what you think.
Mabunny – They are… and super easy to make!
Swishy – They are… do you like all the chocolate dripping off the sides. Not that I let THAT go to waste, of course!
Jules – Mission accomplished! Hope the snack satisfied.
Oh Yum! And I had to come upon these when I’m hungry. ‘Scuse me while I do a refrigerator run……
Ooooh, those look YUM!
Oh wow Michelle, those look YUMMY!
Yummo! Will have to try that recipe out b/c we do like cookies (biscuits here) at my house.
Thanks for stopping by at Trash Towers the other day.
Okay, I have to dash to get ready for dinner with friends, so I will comment more later. But can I just say I have GOT to make these? You’ve put two of my favorite things – chocolate and shortbread – together with another of my favorite things – citrus. Hmmmmm… Angie and I may have to make these when she comes down to visit soon!