Orange Chocolate Shortbread Cookies

These orange chocolate shortbread cookies are a takeoff from the classic thumprint 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 that the animal shelter I volunteer for has 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 off 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)!

How to Make Orange Chocolate Shortbread Cookies

Ingredients
Cookies:
10 T butter, unsalted @ room temperature
3/4 c. brown sugar
zest of one orange
juice of one orange
1 egg
3/4 t. baking soda
1/4 t. salt
3 c. flour

Filling:
1/2 c. cream
8 oz. bittersweet chocolate
2 T Grand Marnier
1/2 c. powdered sugar

Directions
Make the filling first and let come to room temperature before starting the cookies.

Filling:
1. Scald cream in a heavy saucepan.
2. Remove from heat and add chocolate, stirring until fully melted.
3. Add Grand Marnier and stir.
4. Slowly add powdered sugar and stir until combined.

Set aside until cookies are cooled.

Cookies:
0. Preheat oven to 325 degrees.
1. Cream the room temperature butter and brown sugar.
2. Add the orange zest and orange juice, then the egg. Mix until well combined.
3. Add the baking soda and salt, then mix again.
4. Slowly add the flour and stir until fully combined. The dough should be fairly stiff.
5. Roll small amounts of the dough into balls and place onto greased cookie sheet.

Baking:
Using a clean finger or back of an ice tea spoon, make a large, deep divot into each ball (the bigger the divot, the more filling fits!).

Bake each set of cookies 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 ~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 2+ hours for filling to set.

Makes approximately 4 dozen cookies.

Make sure to pin this orange chocolate shortbread cookie recipe to make again!

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