Homemade Milano Cookies

Milano Cookie | The Vanilla Bean Blog | Sarah Kieffer

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.

Milano Cookie | The Vanilla Bean Blog | Sarah Kieffer

homemade hot fudge in a glass jar, with spoon sticking out of it

Cookie Love


‘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!

homemade milano cookies in an aluminum tin

Homemade Milano Cookies

Servings: 3 dozen cookies
Prep Time: 15 minutes
Cook Time: 20 minutes
Additional Time: 45 minutes
Total Time: 1 hour 20 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
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  • 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


  • 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.)


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.


  • Reply
    Tuesday, March 5, 2019 at 6:55 am

    Greetings from Greece. I just love Mlano cookies and since we can’t get them here, I decided to make some. My only question is what type of oven are you using? Conventional(traditional) or convection (air)? Pls specify – for some reason this is never mentioned in almost all recipes. Thank you.

  • Reply
    Alison's Wonderland Recipes
    Thursday, November 19, 2015 at 9:18 pm

    These look so amazing! I LOVE dipping my milanos in tea. I’ll have to make these some time! 🙂

  • Reply
    Tuesday, November 10, 2015 at 11:14 am

    these look like perfection in a cookie biscuit heaven – I will have to give them a go! beautiful photos btw

  • Reply
    Mahée Ferlini
    Wednesday, October 21, 2015 at 4:54 pm

    Great recipe, can’t wait to try it. It’s hard to find a fresh batch in the store. Thank you so much for sharing!

  • Reply
    Monday, September 28, 2015 at 7:36 am

    Those are homemade? No way! That is so cool. This is a very helpful and interseting blog.I love all the foods, quotes and storys you posted. I will visting it a lot.

  • Reply
    Amber Harding
    Friday, September 25, 2015 at 7:06 am

    I made this for work the other day and they were the absolute hit! Lovely looking!

    • Reply
      Friday, September 25, 2015 at 4:21 pm

      I’m so glad to hear you tried them and like them! 🙂

  • Reply
    Monday, September 21, 2015 at 4:38 pm

    Oh God, you have no idea for how long I’ve been thinking about these cookies. Making them used to obsess me a few weeks back when my life was quite busy for baking. Now you remembered me of them – it’s like a tune you barely forgot then someone sings it and you find yourself humming it again 😛
    They look divine and can’t wait to give them a try!

  • Reply
    Monday, September 21, 2015 at 11:03 am

    These look delicious. My 7 yr old son has just started blogging and is into baking. Check out his cookies here –

  • Reply
    Sunday, September 20, 2015 at 2:02 pm

    Very nice cookies! I would enjoy them with tea..

  • Reply
    Friday, September 18, 2015 at 2:38 pm

    you could make dreams come true if you also did mint milano cookies…

  • Reply
    Renee Kemps
    Friday, September 18, 2015 at 1:23 pm

    They look so adorable!!

  • Reply
    Thursday, September 17, 2015 at 6:51 pm

    Milano cookies are my favorite! I have never thought about trying them before.

    Any beginner’s tips?

  • Reply
    Wednesday, September 16, 2015 at 2:50 am

    I really love your photography. Any tips for an aspiring food blogger. BTW love milano cookies can’t wait to try.

  • Reply
    Monday, September 14, 2015 at 1:42 pm

    Just one little niggling question I have: is the overall bake time 10 min or 15 min? I assume you rotate the pans *half way through* and continue baking – so 5 min bake, rotate, 5 min bake – yes? Sorry I’m such a stickler for instructions! Cannot wait to make, thanks for sharing the recipe!!

    • Reply
      Monday, September 14, 2015 at 8:28 pm

      That is a bit confusing; thanks for pointing it out. It should be 15-16 minutes total, so bake 10 minutes, then rotate the pan, and bake 5-6 minutes more. Let me know how they turn out for you!

  • Reply
    June @ How to Philosophize with Cake
    Sunday, September 13, 2015 at 7:11 am

    Oh I just love that quote, I remember reading it and thinking “holy crap could it get any more accurate”. Thanks for sharing 🙂

  • Reply
    Sunday, September 13, 2015 at 12:17 am

    These look amazing!

  • Reply
    Kara | Sorghum and Starch
    Saturday, September 12, 2015 at 12:40 pm

    OMG, homemade milanos?! This is awesome! I know what I’m doing this weekend!

  • Reply
    Cecily @ Burnt Butter Bakery
    Saturday, September 12, 2015 at 2:52 am

    I totally remember underlining the exact same passage in my copy of the Bell Jar when I first read it at fifteen. It’s a scary feeling but liberating too, to know that you have choice. For example, I choose right now to make these cookies, and stuff my face with them!

  • Reply
    Allison from Baking: a Love Story
    Thursday, September 10, 2015 at 12:48 pm

    Seriously? You’re a pretty amazing blogger. We all know you’re slaving away on your book and probably have no time to write and here you quote Sylvia Plath in the most beautiful way, exemplifying everything we (probably) all feel.

    Oh, and the cookies are impressive, too. Hehe.

    Thanks for the inspiration.


  • Reply
    Thursday, September 10, 2015 at 10:39 am

    These look delicious, the homemade version to one of my favorite childhood treats. But I really wanted to drop in and say thank you for the Bell Jar quote. It’s such a stark reminder of the folly of “what-ifs”. I don’t know if you’ve ever seen it, but there’s an artist who did an illustration of this quote a few years ago that I love.

    • Reply
      Thursday, September 10, 2015 at 11:21 am

      Thank you for sharing! I love the illustration.

  • Reply
    madeline | madeline marie blog
    Thursday, September 10, 2015 at 10:25 am

    I just got this cookbook, and now I can’t wait to bake something from it! These look beautiful and just like the real thing–but I’m sure they taste so much better! : )

  • Reply
    Katrina @ Warm Vanilla Sugar
    Thursday, September 10, 2015 at 9:14 am

    Milano cookies are so delicious – I can’t wait to try these at home!

  • Reply
    Thursday, September 10, 2015 at 8:20 am

    I know this is a blog and this is dorky, but I’m low on sleep and I just turned in a manuscript that I finished after seven years at midnight, so I’m a little off my royal rocker this morning: Thank you. For beginning my day with Sylvia Plath and Milano cookies. After last night, it just feels right.

    • Reply
      Thursday, September 10, 2015 at 9:19 am

      Not dorky. Sometimes the words we need to hear find us in odd places. Congrats on turning in your manuscript!

  • Reply
    Thursday, September 10, 2015 at 4:23 am

    Ummmm, these look AMAZING!

  • Reply
    Thursday, September 10, 2015 at 4:02 am

    Hmmm… just love Cookies sandwiched with chocolate – never new they were called Milano cookies though.. Well, never mind thanks for sharing! Now I know what to bake for today’s afternoon tea 🙂

  • Reply
    Mary @ The Kitchen Paper
    Thursday, September 10, 2015 at 12:08 am

    Wow. I love everything about this post. Thanks for sharing The Bell Jar with us! xo

  • Reply
    Heather (Delicious Not Gorgeous)
    Wednesday, September 9, 2015 at 11:51 pm

    i love trying to re-make storebought cookies, but they’re not always successful (yes to samoas, no to thin mints). these ones sound & look like they’d be easy and better than the original. sounds good to me!

  • Reply
    Leticia | Thee Limited Edition
    Wednesday, September 9, 2015 at 11:50 pm

    These cookies are heaven!! I seriously need to make my own batch!!

5 from 1 vote (1 rating without comment)

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