Orange Chocolate Milano Cookies

Last week I wrote about my parmesan pepper bread, which is one of those recipes that you want to make all the time but know you shouldn’t.  These milano cookies DEFINITELY fall in that category.  The soft and chewy (but also dense and filling) butter cookies mixed with the melted orange chocolate filling…mmmm.


The process of piping out the cookies and filling with chocolate can be a bit tedious depending on how many you make, which is just as well since it is probably a deterrent to making these too often.  But seriously, these are amazing.  Good luck having just one once they are ready!

I haven’t had the Pepperidge Farm milanos in years but my memory of them is that they were a bit dry.  I don’t mind a crisp cookie, but who wants a dry one?  The inside of these cookies stay wonderfully moist and chewy while the outside crisps up and browns slightly.


I had a bit of difficulty piping out these cookies and was worried since the sizes varied by quite a bit.  But as I put them together I found that each cookie had a relatively same sized partner, and there weren’t any issues.  When you are spreading on the chocolate filling make sure to leave room at the edges since it will move out when you push the cookies together.


The orange zest that was added to the chocolate filling was a fantastic touch, but I did find it be a bit too strong.  The recipe below calls for the zest of 1 orange, but I might use just half.  Or maybe I just zested a gargantuan orange.  If orange isn’t your thing feel free to leave it out, or maybe add something else in!

Orange Chocolate Milano Cookies (Makes about 2 dozen finished milanos, 4 dozen total individual shortbread cookies)


  • 2 1/2 C AP flour
  • 1 1/3 C sugar
  • 2 eggs
  • 1 egg white
  • 1 C (2 sticks) butter, softened
  • 2 t vanilla extract
  • 1 t salt
  • 8 oz dark chocolate, chopped
  • Zest of 1 small orange (optional)


Preheat the oven to 325 F and line two baking sheets with parchment paper or baking mats.

In the bowl of a stand mixer cream together the butter and sugar.  Add in both eggs, the egg white, and vanilla extract.  Beat on high speed until the mixture is fluffy.  In a separate bowl combine the flour and salt.  Gradually add the flour and salt mixture to the egg mixture while beating on low speed.  Beat just until everything is incorporated.

Transfer the batter to a gallon plastic zipper bag (or a piping bag if you have one).  Force the batter towards one corner of the bag and try to eliminate any air pockets.  Cut a small (about 1/2 inch) hole in the corner of the bag and pipe the batter into 2 inch long strips on your baking sheets.

Bake the cookies for 13 to 15 minutes, just until the edges begin to brown.  Let them cool on the baking sheets for 5 minutes before transferring to a cooling rack.

Melt the chocolate in a double boiler until smooth and add in orange zest if desired.  Let the chocolate cool for 10 minutes.  Spoon chocolate onto the flat part of one cookie and gently press another one on top until the chocolate reaches the edges.  Repeat until all cookies have been used.

Recipe courtesy of Food52.

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