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Homemade Milano Cookies

Eight homemade Milano cookies in a metal loaf tin.
Milano cookies. You know what we're talking about, yes? The buttery cookies made by Pepperidge Farm that are darn near impossible to not inhale by the fistful? This is the homemade version. And they're better than you can even imagine.
Mindy Segal and Kate Leahy

Prep 1 hr 30 mins
Cook 2 hrs 30 mins
Total 4 hrs
36 servings
144 kcal


  • Ateco tip #895 for piping the cookies and filling them with hot fudge


  • 2 sticks unsalted butter at room temperature
  • 1 cup confectioners’ sugar sifted
  • 1/3 cup granulated sugar
  • 1/2 cup whole milk at room temperature
  • 1 tablespoon vanilla extract
  • 2 1/2 cups unbleached all-purpose flour sifted
  • 1 teaspoon kosher salt
  • 1 1/2 cups Hot Fudge (we suggest making this the day before and refrigerating it overnight)


  • In the bowl of a stand mixer fitted with the paddle attachment, beat the butter on medium speed for 5 to 10 seconds. Add the sugars and mix on low speed just until incorporated. Increase the speed to medium and beat the butter mixture until it's aerated (that means fluffy) and looks like frosting, 2 to 3 minutes. Scrape the sides and bottom of the bowl with a rubber spatula to everything together.
  • Pour the milk and vanilla in a liquid measuring cup. In a bowl, whisk together the flour and salt.
  • Add the milk and vanilla to the butter mixture in the bowl and mix on medium speed for 45 seconds to 1 minute, or until nearly completely incorporated.
  • Add the flour mixture to the bowl all at once and mix on low speed until everything just comes together, approximately 30 seconds. Scrape down the sides and mix for another 30 seconds to a minute to ensure the batter is homogeneous. Remove the bowl from the stand mixer. With a plastic bench scraper, bring the batter completely together by hand.
  • Fit a pastry bag with the Ateco tip #895 and fill it with the cookie batter.
  • The most challenging part of making these cookies is piping the batter so that the cookies are the same size. To make it easier, fold sheets of parchment paper into thirds like a business letter, using the folds as a template for piping. (For this recipe, make 4 sheets of parchment paper the same dimensions as a half sheet pan (13 by 18 inches). Fold each sheet of parchment into thirds lengthwise like a business letter. Line 4 half sheet pans with the folded parchment paper and spray with nonstick cooking spray. (Alternatively, if you don't have enough pans, you can put the parchment paper directly on the counter and transfer the paper and piped cookies to a sheet pan when a pan frees up.)
  • Holding the pastry bag at a 90-degree angle, pipe 3 rows of 2 1/2-inch-long strips of batter onto the parchment, up to 20 cookies per pan, using the folds in the parchment paper as a guide. As you pipe, keep the pastry tip close to the parchment paper. To release the cookie batter from the tip, run the tip back over the top of the cookie. Refrigerate the sheet pans until firm, at least 20 minutes, working in batches if refrigerator space is limited.
  • Heat the oven to 350°F (177°C).
  • Bake 1 pan of cookies at a time for 10 minutes. Rotate the pan and bake until the edges are golden brown and the tops are firm, 4 to 6 minutes more. Let the cookies cool completely on the pans. They ought to crisp as they cool. Meanwhile, bake the remaining cookies, 1 pan at a time.
  • When you're ready to assemble the Milano cookies, in a stand mixer fitted with the paddle attachment, whip the hot fudge until it lightens to the color of milk chocolate and looks like frosting, 3 minutes.
  • Fit a pastry bag with the Ateco tip #895 and fill the bag with the hot fudge.
  • Line 2 half sheet pans with parchment paper. Sort through the cookies and pair them in sets of 2 cookies of almost identical or similar size. Turn half the cookies over. Pipe even strips of hot fudge down the length of the upturned cookies, leaving a small amount of room at the ends. Top each frosted cookie with the flat side of a second cookie and press lightly to adhere.
  • Place the Milano cookies on a parchment-lined sheet pan and refrigerate until set before serving. (The cookies can be refrigerated in an airtight container for up to 5 days—as if they'll last that long.)