This recipe for gluten-free Milano cookies is a great example of what I like to call ‘happy accidents.’ A women named Sarah, who worked for me as a pastry chef, brought this recipe to Sweet along with the story of how it came to be. Sarah was originally making a different type of cookie for a party, but the texture came out wrong. She realized that the texture was exactly like Milano cookies, so she filled 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.
At Sweet, we used to make giant, oversized 4-inch cookies, and they always sold out. I am happy to say that when I converted the recipe to gluten free, it came out just as good, if not better, than the original. One of the great things about making your own Milano cookies is that you can make them any size you like. Sometimes I make giant 4-inch cookies. and sometimes I make tiny ones.
As with all of my gluten-free recipes, I have formulated this recipe to work with Bob’s Red Mill 1:1, Better Batter, King Arthur Measure for Measure, Cup4Cup, Doves Farm, and my copycat version of Bob’s 1:1.

Gluten-Free Milano Cookies
As with all of my gluten-free recipes, I have formulated this recipe to work with Bob's Red Mill 1:1, King Arthur Measure for Measure, Cup4Cup, Better Batter and my copycat version of Bob's 1:1.
The classic Milano flavors are plain, mint and orange, but you can have fun with these and use any flavorings you like.
Ingredients
Cookies
- 170 grams unsalted butter, room temperature
- 113 grams cream cheese, room temperature
- 250 grams granulated sugar
- 2 teaspoons vanilla
- 3 large eggs
- 232 grams 1:1 gluten-free flour blend
- ¼ teaspoon kosher salt
Chocolate Ganache Filling
- 226 grams semisweet chocolate (can use milk or dark )
- 56 grams heavy cream
- 1 each zest of orange or mint extract to taste (optional*)
Instructions
Cookies
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Preheat the oven to 325 degrees. Line four baking sheets with parchment or silicone baking mats.
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In a medium bowl, using an electric mixture, beat the butter, cream cheese and granulated sugar on medium-high speed until light and fluffy.
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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.
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Set the batter aside to rest for 30 minutes.
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Transfer the batter to a piping bag or zip-top bag. Fit the piping bag with a large plain tip (½- to 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 2-inches long and at least 1.5 inches apart, onto parchment-lined baking sheets.
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Bake about 18-20 minutes, until cookies are light golden at edges, rotating sheets halfway through. Transfer to wire racks, and let cool.
Chocolate Ganache Filling
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Melt the chocolate and heavy cream in a glass bowl in the microwave for about 1½ minutes, stirring every 30 seconds, until smooth. Add your flavoring, if using.
Assembly
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With a small spoon or offset spatula, spread the melted chocolate on flat side of half the cookies. Sandwich cookie halves together. Cookies can be stored in an airtight container for up to a week.
Recipe Notes
You can also use straight melted chocolate to fill your cookies; however, it is a bit trickier to flavor than the ganache.
If you are flavoring straight chocolate, be sure to use oil-based flavorings or flavorings meant for chocolate -- regular extracts may cause your chocolate to seize.