If you love Milano Cookies, you’ll love these Homemade Milano Cookies. Light and crisp cookies are sandwiched with real semi-sweet chocolate and perfumed with orange zest.

As soon as I posted the recipe for my Crisp Lemon Thin Cookies it immediately became one of my top 10 posts. That was really surprising because it usually takes a while for a new post to move up in the traffic ranking. Clearly you, dear readers, like that recipe as much as I do. Again, sometimes it’s the simplest recipes that are the best.

As soon as I made those lemon cookies, well, really, even before I was done recipe testing, I wanted to make a chocolate-orange version of those cookies.

Who doesn’t love Pepperidge Farm Milano cookies, right? My Crisp Lemon Thin Cookies had a texture similar to Milano cookies, light yet crisp.

It was just a short leap to turn those cookies into my own version of Homemade Milano Cookies. Since chocolate and orange is always a great combination, that’s the flavor combination I went for.

It’s easy to make Homemade Milano Cookies with this recipe

Generally, this is the point in the post where I start to explain all the fails and near misses before I finally got the recipe just right. Well, not this time. These came out exactly as I wanted on the first try. Thanks to my extensive recipe testing for the Lemon Thin Cookies, it only took one shot to get my Homemade Milano Cookies just right.

There were no significant changes to the original lemon recipe, just a simple swap of orange flavorings instead of lemon flavorings.

For the Crisp Lemon Thins I used a scoop to portion the cookies for perfectly round and thin cookies.

To mimic the shape and size of Milano cookies for my Homemade version I piped the batter into strips, about 3″ long and about 1/2″ wide. As they bake, the strips spread to form the iconic oval shape of the original cookies. If you don’t have a piping bag you can scoop the cookies and make round Milanos. They’ll still taste just as good, believe me.

Enjoy!

If you love these cookies as much as I do, please consider leaving a 5-star rating.

Homemade "Milano" Cookies - Chocolate Orange Thins

Name: Homemade "Milano" Cookies - Chocolate Orange Thins
Prep time: 30 min
Cook time: 9 min
Total time: 39 min
Yield: 24
Cuisine: baked goods
Ingredients: 1 stick plus 2 tablespoons (5 oz, 140 g) unsalted butter, room temperature; 1 1/2 cups (6 oz, 170 g) confectioner's sugar; grated zest of 1 orange, divided in half; 1 tablespoon orange juice; 1/2 teaspoon real orange extract; 1 teaspoon vanilla extract; 1 large egg, room temperature; 1/4 tsp table salt; 1/4 teaspoon baking soda; 1 cup (5 oz, 140g) all purpose flour; 8 oz semi-sweet chocolate, chopped

Yield: 24 cookies

Prep Time: 30 minutes

Bake Time: 9 minutes

Total Time: 39 minutes

Homemade Milano Cookies made with light and crisp cookies sandwiched with real semi-sweet chocolate and perfumed with orange zest.

Ingredients

1 stick plus 2 tablespoons (5 oz, 140 g) unsalted butter, room temperature
1 1/2 cups (6 oz, 170 g) confectioner's sugar
grated zest of 1 orange, divided in half
1 tablespoon orange juice
1/2 teaspoon real orange extract
1 teaspoon vanilla extract
1 large egg, room temperature
1/4 tsp table salt
1/4 teaspoon baking soda
1 cup (5 oz, 140g) all purpose flour
8 oz semi-sweet chocolate, chopped

Instructions

Line two baking sheets with parchment paper or a silicone baking mat (see note). Preheat the oven to 350F.
Cream the butter, sugar and half the orange zest until light and fluffy.
Scrape the bowl. Add the orange juice, orange extract and vanilla, mix until well combined. Add the egg and mix until well combined. Scrape the bowl.
Add the salt, baking soda and flour and mix until incorporated.
Use a pastry bag fitted with a 1/2" plain tip to pipe 3" long cookies. Alternately, use a .75 oz scoop or a tablespoon to scoop the cookies onto the prepared baking sheets, leaving 2" between the cookies. They will spread as they bake.
Bake until the edges are golden brown and the middle of the cookies are set, about 8-10 minutes.
Transfer the cookies to a cooling rack and allow to cool completely.
While the cookies are cooling, melt the chocolate in a microwave or over a double boiler. Stir the remaining orange zest into the melted chocolate.
Pair the cookies up by size and shape. Use a small spatula to spread a thin layer of melted chocolate onto the flat side of one cookie in each pair.
Sandwich the cookies and allow the chocolate to set.