Homemade Milano Cookies

About these homemade milano cookies:

You were probably introduced to Milano cookies via Pepperidge Farm, but they can’t compete with the homemade version of this nostalgic treat.
These oval shaped butter cookies are filled with homemade hot fudge, the perfect balance of rich and sweet.

This recipe comes from Cookie Love, by Mindy Segal (Ten Speed Press, 2015), where she reinvents everything from snickerdoodles to chocolate chippers to brownie crinkles!

Piping milano cookies:

I didn’t have an Ateco tip #895 to pipe the cookies, so I snipped a smallish hole in the top of a plastic piping bag (a ziplock bag would work as well) and just used that.
I also found these photos/directions on Food 52 super helpful!

I thought the cookies tasted best on the first day – they get soggier as the days progress, and I preferred them crisp. It’s also helpful to make the hot fudge at least a day in advance.

Musings:

‘I saw my life branching out before me like the green fig tree in the story. From the tip of every branch, like a fat purple fig, a wonderful future beckoned and winked.
One fig was a husband and a happy home and children, and another fig was a famous poet and another fig was a brilliant professor, and another fig was Ee Gee, the amazing editor, and another fig was Europe and Africa and South America, and another fig was Constantin and Socrates and Attila and a pack of other lovers with queer names and offbeat professions, and another fig was an Olympic lady crew champion, and beyond and above these figs were many more figs I couldn’t quite make out.

I saw myself sitting in the crotch of this fig tree, starving to death, just because I couldn’t make up my mind which of the figs I would choose.
I wanted each and every one of them, but choosing one meant losing all the rest, and, as I sat there, unable to decide, the figs began to wrinkle and go black, and, one by one, they plopped to the ground at my feet.’ – Sylvia Plath, The Bell Jar

(We can’t have it all. We just can’t be everything.)

More Cookie Recipes!

• Pan-banging Chocolate Chip Cookies
• Olive Oil Sugar Cookies with Pistachios and Lemon Glaze
• Cheesecake Cookies

Homemade Milano Cookies

Servings: 3 dozen cookies

Prep Time: 15 minutes minutes

Cook Time: 20 minutes minutes

Additional Time: 45 minutes minutes

Total Time: 1 hour hour 20 minutes minutes

Rich, buttery cookies are filled with a hot fudge filling to make these homemade Milanos, a nostalgic treat!

Sarah Kieffer

5 from 1 vote

Print Pin Rate

Ingredients

• 2 sticks 8 ounces unsalted butter, at room temperature
• 1 cup powdered 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

Hot Fudge Filling

• 3 cups heavy cream
• 1 3/4 cups granulated sugar
• 2 tablespoons golden syrup or light corn syrup
• 4 ounces unsweetened chocolate broken into pieces
• 1 1/2 teaspoon kosher salt
• 1/4 cup 2 ounces unsalted butter, at room temperature
• 2 tablespoons pure vanilla extract

Instructions

• To make the hot fudge: In a 6-quart or larger heavy pot over medium-high heat, combine the cream, sugar, and syrup until dissolved, approximately 3 minutes. Add the chocolate and salt and bring to a boil. Lower to a gentle simmer so that the bubbles percolate in the center of the pot. Cook, stirring periodically to avoid scorching the bottom, until the mixture breaks and the oils separate from the solids, 40-45 minutes.
• Whisk in the butter and vanilla thoroughly (you can also use an immersion blender to do this if you want it extra smooth) and let cool. Hot fudge keeps in the refrigerator for up to 6 months.
• In the bowl of a stand mixer fitted with the paddle attachment, mix the butter on medium speed for 5 to 10 seconds. Add the sugars and mix on low speed to incorporate. Increase the speed to medium and cream the butter mixture until it is aerated and looks like frosting, 2-3 minutes. Scrape the sides and bottom of the bowl with a rubber spatula to bring the batter together.
• Put the milk and vanilla in a liquid measuring cup.
• In a bowl, whisk together the flour and the salt. Add the milk and vanilla to the butter mixture and mix on medium speed for 45 seconds to 1 minute, until nearly incorporated.
• Add the flour mixture all at once and mix on low speed until the dough 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 dough completely together by hand.
• Fit a pastry bag with the Ateco tip #895 and fill with the cookie dough.*
• 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. 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 non stick cooking spray.
• Holding the pastry bag at a 90-degree angle, pipe 3 rows of 2 1/2 inch-long strips of dough onto the parchment, up to 20 cookies per pan, using the folds in the parchment as a guide. As you pipe, keep the pastry tip close to the parchment paper. To release the cookie dough 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. After 10 minutes, rotate the pan and bake until the edges are golden brown and the tops are firm, 4-6 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.)

Notes

Recipe reprinted from Cookie Love, by Kate Leahy.

* I didn’t have an Ateco tip #895 to pipe the cookies, so I snipped a smallish hole in the top of a plastic piping bag (a ziplock bag would work as well) and just used that.