In December of 1997 I spent all of my babysitting money on a pair of boots from JCrew. True story. Because I was broke I started making cookies to give as holiday gifts to teachers and friends, and in order to help my mother bought me a $3.00 “Pillsbury Holiday Cookie” booklet.
Sadly, that cookie booklet is lost, but 25 years later one recipe is still part of my cookie rotation: Chocolate Chip Orange Shortbread. I know in January we’ve all had enough cookies, but I promise you’ll find room for these. With a subtle orange flavor that accentuates the chocolate instead of dominating it, they are buttery, the right kind of crumbly, and absolutely perfect.
Notes
A note about shortbread
I usually hate working with short bread. I hate the way it falls apart in clumps! I hate having to roll the dough and freeze it in plastic wrap! I hate how it always looks messy! These “pizza slice” cookies solve all of these problems: They look gorgeous without being a nightmare to make. And while you can expect there to be some flakey/clumpy bits when you roll the dough into discs, you can just smoosh those bits back in because the chocolate “pizza crust” will cover any mess.
A note about orange peel
The original recipe called for freshly grated orange peel. Rosalie from 1997 used dried orange peel… I’m not really sure why, but my 16 year old self had the right instincts. Fresh orange makes these cookies tastes medicinal. The dried stuff found in the spice aisle works way better here.
Key Ingredients
1 cup powdered sugar
1 cup and 1 tablespoon butter
1 1/2 teaspoon vanilla
1 tablespoon dried orange peel
1 3/4 cup all purpose flour
1/4 cup corn starch
1.5 cups mini chocolate chips
2-3 tablespoons milk
Recipe – Chocolate Chip Orange Shortbread
Adapted from Pillsbury “Holiday Cookie Cookbook.” Makes 32 cookies. Prep time: 15 minutes for cookies plus 10 minutes to dip cookies in chocolate. Cook time 22-30 minutes.
Ingredients
Cookies:
- 1 cup powdered sugar (115 grams)
- 1 cup butter, softened
- 1 teaspoon vanilla
- 1 tablespoon dried orange peel
- 1 3/4 cup all purpose flour (240 grams)
- 1/4 cup corn starch (32 grams)
- 3/4 cup mini chocolate chips
Glaze:
- 3/4 cup mini chocolate chips (this recipe uses most of the mini chips in a 10 oz bag)
- 1 tablespoon butter
- 2-3 tablespoons milk (see note about microwaving chocolate)
- 1/2 teaspoon vanilla
Step One
Preheat oven to 325 degrees.
Using the whisk attachment on a mixer (or a hand mixer), beat the powdered sugar and butter on medium high until fluffy. Add dried orange peel and vanilla, and mix on medium-low until incorporated. Next, stir in flour and corn starch until incorporated, then stir in 3/4 cup mini chocolate chips.
Step Two
Divide dough into 4 equal parts. Shape each part into a ball (see photos above) and then press the cookie ball flat onto an ungreased cookie sheet. Two balls of cookie dough per sheet pan works best. I used parchment paper because my cookie sheets look gross. I PROMISE you should just use an ungreased sheet.
Step Three
Using a rolling pin or just your palms (my preferred method) flatten and shape each ball into a 1/4 inch thick disc (see photos above). Reincorporate any edges that break using your fingers to mold crumbs back in place. It’s short bread so it’s going to happen.
Step Four
Use a knife to cutting about halfway through the cookie dough in 4 intersecting lines, scoring 8 wedges into each disk. Like you’re cutting a pizza. Bake for 22-30 minutes. Until the outside edges start to look toasty. Cool for 5 minutes then use a knife to slice the rest of the way through the cookies and separate them. Allow cookies to cool completely.
Step Five
Melt the remaining butter, chocolate chips, vanilla, and milk until smooth. You can use either a double boiler or microwave. (If you’re using a microwave to melt your chocolate mixture make sure you stir it frequently. You may also need an additional 1 tablespoon of milk to keep the chocolate from drying out). Once chocolate mixture is smooth remove it from heat and dip the rounded edge of each cookie into it to make a “crust” edge on your cookie. Wipe any excess chocolate from the bottom of the cookie and place on parchment or wax paper until chocolate cools and hardens.
Store cookies in a covered container. They’ll keep on the counter for about 10 days.