Gluten Free Milano Cookies

Gluten Free Milano Cookies

Do you have a favorite pre-gluten-free cookie? For many of us, store-bought cookies with names like Pecan Sandies, Nilla Wafers and Milano Cookies bring back truly yummy memories. Don’t let the fact that you can’t grab a Pepperidge Farm Milano Cookie bag and eat them by the fistful anymore; make new yummy memories by baking your own gluten free Milano cookies! (oh and by the way, I have gluten free recipes for those other classics, too – just click on the cookie name to hop to the recipes!)

gluten free milano cookies on tray

This recipe is super easy, but you’d never know it if you saw my recipe notes! I can’t even remember how many versions of this gluten free Milano cookie recipe I made. With and without eggs; with confectioner’s sugar, with granulated sugar, with a blend; with and without leavening; with and without flavored extracts; with softened butter and with cold butter … I kid you not, they were all yummy in their own way since they were made with my soft and smooth gfJules Flour, but accomplishing that classic Milano cookie texture was at first elusive.

I netted out that egg helps them be snappier, but applesauce is a perfectly acceptable vegan substitute, it just makes a cakier, chewier cookie. Oh, and definitely use granulated sugar, NOT confectioner’s sugar, as you’ll never get any crunch out of them with powdered sugar instead.

I like the cold butter (I actually use Earth Balance) version, but there wasn’t much of a difference if I let the butter sit out longer. The subtle flavor imparted with the lemon extract really was a nice addition, but you can skip it if you don’t have any on hand. Your choice whether to add flavors to your chocolate middles – that’s a very personal preference.

gluten free milano cookies with tinkertoys

In the process of trying all these different variables, I learned some interesting facts about the history of the classic, now my gluten free Milano cookie. Did you know that Milano cookies were originally just one vanilla wafer-type cookie topped with dark chocolate, but in shipping they would stick together and make a mess of themselves. The solution? Sandwich the chocolate between two cookies so they were stuck together intentionally. Pretty brilliant, actually.

making gluten free milano cookies

This trick makes the cookies easy to make similarly sized.

 

So I give you this recipe not only so you can make them anytime you have the craving for Milano cookies, but also so you can make fun desserts like this gluten free graveyard full of homemade gluten free and vegan chocolate pudding (so decadent!) for Halloween. Seriously, how fun is that? And it’s all made possible because of this gluten free Milano Cookie recipe!

gluten free graveyard for Halloween

To make this spooky graveyard, melt about 1/4 cup chocolate chips, then spoon into a snack bag with one corner cut out in a tiny slit. Squeeze warm chocolate through the hole to write RIP on the cookies. Arrange in a bowl full of my gluten free and vegan chocolate pudding. Crush gluten free Oreo-ish cookies (like Glutino brand), if you like, and sprinkle around the graves.

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Gluten Free Milano Cookies

gluten free milano cookies in bag

5 from 3 reviews

  • Author:
  • Prep Time: 20 minutes
  • Cook Time: 15 minutes
  • Total Time: 1 hour
  • Yield: ~16-20 cookie sandwiches

Ingredients

Instructions

Preheat oven to 350° F or 325° F convection.

Prepare a baking sheet by lining with parchment paper. Have a large zip-top bag ready for piping dough.

Whisk together the gfJules Flour and salt in a small bowl and set aside.

In a mixing bowl, cut the cold butter into smaller pieces and cream together with sugar until light and fluffy – at least 2-3 minutes. Add the extracts and beat again to integrate.

Add applesauce or egg, alternating with the blended gfJules Flour/salt mixture; beat just until a stiff dough forms.

Scoop dough into the zip-top bag and squeeze it into the bottom of the bag. Cut off a  1-inch diagonal from one corner of the bag. Squeeze dough out of the corner to form even 2 inch long cookies. They will not spread very much, so you can line up cookies to fill the cookie sheet, leaving only and inch or so in between them, if need be.

Once all the cookies are piped out, wet your fingers or a rubber spatula and go over the cookies lightly to press them flatter and smooth out the ends. The flatter they are before they go into the oven, the crunchier they’ll be once baked, so decide if you want crunchier or chewier cookies.

Bake in preheated oven for 15 minutes, then check to see if the bottoms are lightly browning. If not brown yet, return to the oven and continue to bake for another 2-4 minutes, watching to make sure the cookies do not get too brown.

Remove to cool on a wire rack.

Select pairs of cookies which are approximately equal in width and length and arrange together so they are ready for the chocolate.

Once fully cooled, melt chocolate in a double boiler, chocolate pot, or glass bowl in a microwave (approximately 1 ½ minutes, depending on microwave strength), stirring frequently to ensure the chocolate does not burn. If adding flavored extract to the chocolate, whisk it into the melted chocolate once smooth.

Using an offset spatula or butter knife, apply melted chocolate to the underneath side of one of each pair of matched cookies. At first, the chocolate will be shiny; as it cools, it will no longer be shiny.

Press a matching cookie on top of each chocolate-topped cookie just before the chocolate is no longer shiny. By waiting until then, the chocolate will have mostly set and won’t run out the sides of the cookies when pressed together, but it will still be warm enough to melt into the top cookie.

Store cookies in an airtight container for up to 5 days.

Notes

Recipe works well doubled!

Gluten Free Mock Milano Cookies | gfJules

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21 thoughts on “Gluten Free Milano Cookies

  1. These are perfect for the holidays and look so much better than store bought cookies and I bet taste better! Plus they’re gluten free so everyone can safely enjoy them.

  2. OMG, those Pepperidge Farm cookies were SO popular when I was growing up. Your version looks better though – a little thicker and you can use as much filling as you want. I like to use extra 🙂

    • Hi Ed – fixed! For some reason when I transferred the recipe from my word document into the website, an entire paragraph went missing! Hope you can make the recipe with all the directions now!
      ~jules

  3. I used to eat these sweets all the time as a child! I would love to try making them homemade for the holidays 🙂 What great memories these treats bring back. I appreciate you providing easy egg-free & dairy-free substitutions.