Ingredients
- 10 tablespoons (1 stick plus 2 tablespoons) unsalted butter, softened at room temperature
- Freshly grated zest of 2 medium oranges
- 2/3 cup sifted confectioners’ sugar
- 3/4 teaspoon pure vanilla extract
- 1/8 teaspoon salt
- 1 1/2 cups sifted flour
- Confectioners’ sugar for dusting
- Cookie filling, recipe follows
- 1/2 cup sifted unsweetened cocoa powder
- 2/3 cup granulated sugar
- 3 tablespoons unsalted butter
- 1/3 cup heavy cream
Instructions
- Preheat the oven to 325 degrees.
- In a mixer fitted with a paddle attachment (or using a hand mixer), mix the butter, orange zest and confectioners’ sugar until light and fluffy. Add the vanilla and salt and mix. Add the sifted flour and mix until smooth. Refrigerate 30 minutes. On ungreased cookie sheets, working in batches if necessary, drop level teaspoons of the chilled dough 2 1/2 inches apart. One by one, pick up the dough balls, roll into a smooth ball, and replace on the cookie sheet. Spread about 3 tablespoons of confectioners’ sugar on a plate. Dip the bottom of a drinking glass into the sugar and use it to press the dough balls flat, into 1 1/4-inch circles. Repeatedly dip the glass into the sugar as needed to keep the bottom dry and coated. Bake until golden brown around the edges, 12 to 15 minutes. Let cool on the cookie sheets for 2 minutes. Transfer to wire racks and let cool completely.
- To assemble the cookies, liberally spread half of the orange cookies with cocoa filling, keeping the filling a little bit away from the edges. Cover with a plain cookie and press together gently to create a sandwich. Store in an airtight container.
- Filling: In a small bowl, mix the cocoa and sugar. In a saucepan, melt the butter over low heat. Add the cocoa mixture and the cream and cook, stirring, until thickened, about 3 minutes. Set aside to cool; the mixture will thicken as it cools.
Reviews
Awesome! In order to get a more orange flavor I put the orange zest in the butter while creaming then added the remainder of the ingredients. I also put orange zest in with the chocolate filling. This gave the perfect orange and chocolate flavor . It is time consuming but well worth it!
I agree with wanting to have a stronger orange flavor. Next time I might try adding a touch of orange extract to the cookie dough. But they are still delicious and festive. I got 12 sandwich cookies from this recipe, would definately have to double if taking to a party or cookie exchange!!
I want to make these cookies for a cookie exchange but how many sandwich cookies does this recipe make??? can’t find that anywhere on the recipe.
Delicious..wish the orange flavor was a little stronger..i love the chocolate filling!
These cookies are, hands down, my family’s favorite. They’re not very difficult but a little time-consuming…but they’re worth it! The only change I make is to dip the glass in granulated sugar instead of confectioner’s sugar for pressing the cookies flat. The filling amount is right, and the cookies are spot on.
I made 8 different kinds of cookies for Christmas and these were the favorites of the family. I made it exactly as directed. Didn’t change anything. I used Droste cocoa powder. The filling just needs to have a thin layer and it does stay in the cookie once it cools. Just set the top on the “sandwich” lightly and let it cool.
These taste like a Milano cookie only with a hint of orange. My family just loved these cookies.
These taste like a Milano cookie only with a hint of orange. My family just loved these cookies.
grandma cookie better with no orange and vanilla cream
I first made these three years ago for Christmas cookies. They were a big hit at my school. The chocolate/orange combo is so tasty! These could become an addiction! They do take a little bit of time to make, but it’s worth it to me.
I really enjoyed the orange cookies but it was a lot more time consuming than I’d thought. Since I was crunched for time I used Nutella for the filling but think a darker chocolate would have worked better. Delicious but not worth another go.
I made mine a little different…i didn’t use confectionary sugar..just plain granulated sugar..it came out a little different..quite different actually..but i added more flour and butter and it worked. Couldn’t use the cup method, so i used my fingers to press it down instead. For the chocolate, i added too much cream and it didn’t quite thickened the way its supposed to be..placed it in the fridge and it’s kinda like fudge now..so instead of sandwiches, i just scooped some onto a slice of cookie and ate it..Very nice..and very rich..the orange zest, i added only as i didn’t want it too heavy. Really subtle flavour..NICE! and easy too