Keto Milano Cookies

Better than Pepperidge Farms and healthier too! These homemade Keto Milano Cookies are buttery and delicious, with a sugar-free dark chocolate filling.

Successfully making over an old favorite cookie into a keto treat makes me very, very happy. And these homemade mint milanos made me so happy, I may have danced around my kitchen a little bit. Or a lot bit. And my middle child loved them so much, she danced around with me. It was quite a sight!

Remember those delicious packaged Milano Cookies from the old, high carb days? I certainly do and I can practically taste them. They were a really special treat, and we didn’t get them often.

And when I was a child, they weren’t available in Canada. So we only got the Milano Cookies when we were on vacation in Florida. My father’s wife loved them so much, she would stash them on the highest shelf in the condo kitchen, and only doll them out a little at a time. We weren’t allowed to get them ourselves, as they were “adult cookies”. Meaning the adults ate most of them and they only shared once in a while!

With that kind of special, limited access, it’s no wonder I have fond memories. And no wonder I wanted to come up with a healthy keto milano cookie recipe of my own.

What are Milano Cookies

If you aren’t familiar with these lovely treats, let me enlighten you. Made famous by Pepperidge Farms, they are oval shaped sandwich cookies. The cookies are crisp and light, like a butter cookie, and the filling is rich chocolate ganache.

Back in my day, they only had the regular chocolate version and the mint chocolate version. Now they have all sorts of crazy Milano Cookie, such as banana, key lime, and toasted marshmallow.

I always loved that hint of mint in the Mint Milanos. And so I decided to make these with a little mint extract. But you can leave that out if you prefer.

Creating Keto Milano Cookies

Perfecting this keto cookie recipe took a little experimentation, I must admit. Getting that light, airy cookie just right was of the utmost importance. I consulted a number of conventional Milano cookie recipes, such as this one from Handle The Heat.

Piping the cookies properly took a little practice. I found that when I tried to keep the whole in my piping bag on the small side, I didn’t get enough dough coming through. But cutting it to 1 inch seemed just about right.

I did end up with a few blobs of cookie dough that weren’t nice logs, but it was easy to scoop that off of the pan and put it back into the piping bag.

I also found that the cookies were quite soft at first and needed more crisping up. So I resorted to my old trick of putting them back into the warm oven to keep drying out. Worked like a charm, as always.

Tips for making Keto Mint Milanos

Room temperature ingredients: How often do you hear me say how important this is? But in these light, crisp cookies, it’s vitally important, so your butter doesn’t clump up and leave holes in your cookies.

Powdered Swerve Sweetener is the ideal sweetener for these keto Milano cookies. It’s fine enough to blend into the dough perfectly, but also helps make the cookies crisp. Nothing but a finely powdered erythritol based sweetener will work if you want that crispness.

Silicone baking mats will protect the bottoms of your cookies better than parchment, and allow you let them crisp up longer in the oven. I have three in various sizes and I use them constantly.

Let them cool completely. Another keto baking tip I find myself repeating over and over. These are delicate little cookies so you want them to cool fully before attempting to remove them from the pan.

The chocolate filling is best done in a saucepan, even though it’s such a small amount. I find it’s much less prone to seizing than if you do it in a microwave.

Peppermint extract comes in both oil based and alcohol based varieties. If you can, get the oil based ones, as they are less likely to make the chocolate seize when you add it. I prefer this one from Frontier.

Love to bake? Then you need The Ultimate Guide to Keto Baking!