This recipe for homemade giant Milano cookies is a great example of what I like to call ‘happy accidents.’ A women named Sarah who worked for me brought this recipe to Sweet along with the story of how it came to be. She was originally making a different type of cookie for a party, but the texture came out wrong for her intended plan. She realized that the texture was exactly like Milanos, so she stuffed them and a new recipe was born. Being a huge fan of Milano cookies since I was a child, I for one am thrilled that this ‘mistake’ happened — and I think you will be too.
Want to Learn More About Making Holiday Cookies?
If you would like to become more confident making cookies, you’ll love my Holiday Cookie class. Instead of just following one recipe, you’ll learn the techniques, ingredient choices, troubleshooting tips, and step-by-step methods that help you get consistent results every time. Plus, every class includes multiple recipes, printable guides, flavor variations, and plenty of chef tips that go far beyond what I can fit into a single recipe post.
👉 Learn more about the Holiday Cookie class here.
Looking for Ongoing Help?
If you’re ready to really master gluten-free baking, I’d love to welcome you into my Gluten-Free Baking Bootcamp. Bootcamp is my guided membership where you’ll get access to my complete library of classes (150+), bake/ cook live on zoom with me every month, weekly live Q&A sessions, recipe conversion help, and an incredibly supportive community of gluten-free bakers. Whether you’re just getting started or you’ve been baking for years, you’ll always have expert guidance whenever you need it.
👉 Learn more about Gluten-Free Baking Bootcamp here.
Homemade Giant Milano Cookies
Ingredients
Cookies
- 6 ounces unsalted butter, room temperature
- 4 ounces cream cheese, room temperature
- 1¼ cups granulated sugar
- 2 teaspoons vanilla
- 3 large eggs
- 1⅔ cups all-purpose flour
- ¼ teaspoon kosher salt
Filling
- 8 ounces semisweet chocolate (can use milk or dark )
- ¼ cup heavy cream
- Zest of one orange (optional)
Instructions
Cookies
- Preheat the oven to 325 degrees.. Line four baking sheets with parchment or silicone baking mats.
- In a medium bowl using an electric mixture, beat the butter, cream cheese and granulated sugar on medium-high speed until light and fluffy.
- Add the vanilla and eggs (one at a time), and beat to combine. With mixer on low, gradually add the flour and salt, and beat until just combined.
- Transfer the batter to a piping bag or zip-top bag. Fit the piping bag with a large plain tip (½-¾ inch), or snip a ¾-inch hole in one corner of the zip-top bag. I strongly recommend using a proper piping bag and tip.Holding the bag at about a 90 degree angle, pipe cookies that are four-inches long and at least 1½ inches apart onto baking sheets.
- Bake 18-20 minutes, until the cookies are light golden at edges, rotating sheets halfway through baking. Transfer to wire racks, and let cool.
Frosting
- Melt the chocolate in a glass bowl in the microwave for about 1½ minutes, stirring every 30 seconds, until smooth.
- With a small spoon or offset spatula, spread the melted chocolate on flat side of half the cookies. Top the chocolate-covered cookies with the remaining half of the cookies. Cookies can be stored in an airtight container up to a week.
