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!
Keto Mint Milano Cookies
Ingredients
Cookies
- 1/2 cup butter, softened
- 1/2 cup powdered Swerve Sweetener
- 1 large egg, room temperature
- 1 large egg white, room temperature
- 1 tsp vanilla extract
- 1 1/4 cup almond flour
- 1/4 tsp salt
Chocolate Mint Filling
- 1/4 cup heavy cream
- 2 ounces sugar-free dark chocoate, chopped
- 1 tsp mint extract
Instructions
Cookies
- Preheat the oven to 325F and line two baking sheets with silicone mats. You can use parchment instead but keep a close eye on your cookies as the bottoms may brown quickly.
- In a large bowl, beat the butter with the sweetener until light and fluffy, about 2 to 3 minutes. Beat in the egg, egg white, and vanilla until well combined.
- Add the almond flour and salt and beat until the mixture is uniform, scraping down the sides of the bowl and the beaters as necessary.
- Cut a 1 inch diameter hole in a piping bag and fill with the dough. Pipe 2 inch long logs onto the prepared baking sheets, leaving at least 2 inches between each cookie.
- Bake 18 to 25 minutes, until the edges are golden brown, and turn the oven off. Remove and let cool 15 minutes, then return to the still warm oven for another 15 to 20 minutes, keeping your eye on them, to help them crisp up.
- Let cool completely before filling.
Chocolate Mint Filling
- In a small saucepan over medium low heat, bring the cream to just a simmer. Remove from heat and add the chopped chocolate. Let sit 5 minutes to melt.
- Add the mint extract and whisk until smooth and thick. Spread the bottom of one cookie with about 1 teaspoon of the chocolate filling. Top with another cookie. Place on a cooling rack until firm.
Nutrition
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Hi! Bought the new baking book, and I was so impressed that I bought 3 more of your books! Lost 30 lbs on low carb but have gained back 20 ???? and sweets were a part of the downfall. I am refocused but know that I can’t do it without sweets somehow. Enjoying chocolate mayonnaise cake this week.
Hubs loves regular Milanos, but my favorite is orange Milano. If I remember right, there’s chocolate in the middle, but then also a slick of orange frosting on either side of the chocolate. right?? Anyway, how would you recommend getting the orang part in there for an Orange Milano? Also wondering if you’ve got a recipe for toffee bars? The bar cookie, I mean.
Love your name, btw—there aren’t many of us out there! —Carolyn
Thanks, so glad you like the book. I think you could maybe do just a bit of orange buttercream, maybe with a touch of cream cheese to give it structure. I am not sure what you mean by toffee bars but I do have a pecan toffee bar, and I also have keto cracker toffee. Just use the search term “toffee” in my search box and you will find them!
Can I use a plastic bag cut for the filling instead of a bag?
These look amazing
Sure, any Ziploc bag will do.
Would it be cheesy to nominate you for sainthood? Because these cookies are freaking AMAZING!
I’m all for it! 😉
Yassssss! I love healthier versions of my favorite treats! Looking forward to trying these!
Milano cookies are my FAV, and these were absolutely delicious! Making them again and again!
Mine completely flattened and spread out, like paper thin. I followed your recipe exactly, what went wrong?
Sounds like you needed a bit more almond flour. They can vary so much brand to brand. I’d try adding another 1 to 2 tbsp. Do the paper thin crisps taste good at least? Drizzle them with some chocolate and enjoy…
Yes they taste great! I will try to add more almond flour, what should the consistency by like?
Hard to explain but it should be thick enough to be scoopable, and it shouldn’t glop out of the pastry bag, you should have to squeeze it to get it to come out (not hard, but some pressure).
Next time I will take pictures, they looked just like the original milano’s. We love this cookies. Our favorite keto cookies so far. Thank you for all the recipes.
Glad they worked out!
Would these work with powdered xylitol? Any erythritol sweeteners make my tongue numb!
Amelia x
Nope. They won’t crisp up at all with xylitol. Please read this: https://alldayidreamaboutfood.com/best-keto-sweeteners/
Yummmmmm! I made these tonight for Super Bowl Sunday snacks tomorrow. Super delicious! I’m confused though, a couple of comments ask how many cookie sandwiches it makes, and the recipe says it should make 24 sandwiches. Mine made 24 cookies , and 12 sandwiches. Maybe I made each cookie too big, and they needed to be smaller so I can get 48 cookies, and 24 sandwiches? Either way, I have 24 ovals of deliciousness! Thank you for another great recipe!
Yes your cookies definitely turned out too big but… you clearly have something delicious so just go with it. Just watch the portion size. 😉
Made these and they are wonderful. My question do they need to be stored in the refrigerator? That is, if there are any left.
No fridge, they will get too soft. I stored mine in a covered container on the counter for up to 5 days.
Hi, I made these but they did not crisp up. I followed all directions and even though they do taste very much like the originals, they were not crispy. Thanks for all the recipes you share online. I have 2 of your books and love all your recipes.
What sweetener did you use?
Swerve
Do these cookies freeze well?
They should freeze just fine.
Got these in the oven now! Quick question- when returning them to the “warm” oven to crisp up, does that imply you turned the 350 degree oven off and put the cookies back in 15 minutes later at whatever temp the oven coasted down to OR do you leave the oven at 350 for Round 2?
Thanks!
Yes, it means the oven off with residual heat.
OMG the non low carb version is sooo good… one of my most favorite cookies when I was eating sugar! I can’t wait to try this keto version! I will be making them as part of my Keto snack meal for Super Bowl Sunday!
I WILL be making these!!! But, I’m wondering if I can leave out the mint? Not everyone in my family likes mint as much as I do.
Of course and if you read the blog post, I do say that.
looks deliious! how do you calculate the nutrition facts for your recipes?
Hi there… please read the nutritional disclaimer at the bottom of the post. That explain it all. thanks!
Have you tried letting them dry out before baking like macarons?
No and that’s an interesting thought. May try that next time!
This looks amazing! I do have a questions that I would like clarification on. You have 1 large egg and 1 large egg white. Is the one large egg just the yoke or does that include the egg white also along with the egg white of another egg. Thanks
1 large egg = one WHOLE egg. White and yolk together.
Does the recipe make 12 or 24 sandwich cookies? Is the serving size 1 or 2 sandwich cookies! I appreciate your help in understanding. I know my family will love them and I want to be sure to make enough. Thanks for all of the fabulous recipes. 🙂
It makes 24 sandwich cookies. Please always check the nutritional info card for # of cookies per serving (in this case 2).
Just to piggy back on original question . Serving size is 2 cookies. 2 sandwich cookies or 2 cookies = 1 sandwich cookie per serving . Just trying to get my macros as accurate as possible. Thank you!
Two sandwich cookies = 1 serving.
I just made this and I only got 12 whole sandwich cookies. Also mine flattened a lot more than the picture indicates.
Sounds like you made them much bigger than I did. Also sounds like there wasn’t quite enough flour in yours to help them hold their shape. What brand of almond flour were you using?
When returning to the warm oven for the final crisping, do you turn the oven off and use the residual heat or leave it at 325? I can not wait to try theses!!
The oven should be off but retaining any residual heat.
Thank you!
It says to turn off the heat.
I am allergic to almonds so any recipe with almond flour is out for me. Is there a guide I can use for substitutions? I love your recipes!
This recipe looks amazing! While heavy cream is such a delicious ingredient, is there a way to make the filling without using cream? (I’m off dairy). Could you use coconut oil and the chocolate? Any help would be greatly appreciated.
Are you eating butter? Because the cookies really are best with butter, I think. You could easily use coconut cream in the filling, though. It tends to be a little thinner that way so you may need a bit more chocolate.
My old non-keto recipe for Milano cookies from years ago has a filling made from 3 oz semisweet chocolate and 1 T vegetable shortening (i.e. hydrogenated soybean oil). It would probably work to use palm oil or maybe a mixture of palm oil and avocado oil. Maybe adding just a bit of avocado oil work work. Experiment to get a texture you like and post the results. 🙂 The reason for adding the fat is to thin the chocolate so the filling isn’t just solid chocolate, which has the wrong texture—too hard. I think coconut oil is too hard to do that unless your house is hot enough that coconut oil is liquid. If you do this, instead of making a ganache, you don’t have to worry about the chocolate seizing.