Strawberry Milano Cupcakes

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As a busy mom, I rarely take time just for myself these days. But one little ritual I cling to is what I call my daily “Milano Moment.”

Each afternoon, I allow myself exactly three mini Milano cookies with my cup of tea. I savor every crumb of that crisp, buttery cookie sandwiching luscious strawberry cream.

It’s just a small treat, but that brief time spent nibbling these pillow-soft cookies makes me feel pampered.

Of course, my biggest dilemma is stopping at just three cookies! Milanos are my ultimate weakness and those addictive strawberry ones especially seem to disappear at my house.

I blame pregnancy cravings…this baby has expensive taste apparently! But I know plowing through a whole bag defeats the purpose of a “moment.”

So to satisfy my strawberry Milano obsession in a more portion-controlled way, I decided to transform the flavors I love into these gorgeous cupcakes swirled with a creamy strawberry frosting.

Each tender vanilla cupcake hides a strawberry Milano center for the perfect bite. Now when Strawberry Milano cravings hit, I can indulge in one special little cake and feel like I’m getting my fix!

Why You’ll Love Strawberry Milano Cupcakes

  • They satisfy your Milano craving! All the iconic flavors of strawberry and chocolate sandwiched between crisp, buttery cookies now in cupcake form.
  • Fancy looking but easy to make. With a simple vanilla cupcake base, these look gourmet but come together quickly.
  • Portion control for indulging. Unlike cookies that you nibble mindlessly through a whole sleeve, one little cupcake feels special.
  • Kid-friendly but sophisticated. Simple flavors made elegant with lush buttercream frosting swirls.
  • Easily customized. Swap out strawberry buttercream for any flavor or frosting you love!


  • Finely chop the Milano cookies so they distribute nicely throughout the cupcake batter rather than sink.
  • Make sure cupcakes are completely cool before assembling or frosting will melt. Refrigerating briefly helps too.
  • Use seedless strawberry jam rather than pieces if you want smooth frosting. Or puree fresh strawberries instead!
  • Pipe frosting with a star tip for fancy swirls, but a simple knife spread works great too, especially for beginners.
  • Garnish with fresh berries, sliced strawberries or even extra crumbled Milano cookies on top.

The Ingredients

Milano Cookies

Chopped into pieces and swirled into the batter, these iconic chocolate and strawberry sandwich cookies are the star ingredient! That familiar crisp, buttery cookie texture within tender vanilla cupcakes is heaven.

Strawberry Puree

Since strawberry jam would make the frosting seedy, using blended fresh strawberries ensures a smooth, fruity swirled frosting that perfectly matches the interior Milano flavor.

Butter & Sugar

Lots of creamy butter in both the cupcakes and especially the frosting gives that rich mouthfeel you expect from a Milano. And a generous amount of sugar balances the tart berry flavors.

How to Make Strawberry Milano Cupcakes

Prepare the Cupcake Batter

Whisk together  flour, baking powder and salt.

In another bowl, cream butter and sugar until fluffy.

Beat in eggs, vanilla and milk.

Add in dry ingredients, mix until incorporated.


Finally, gently fold in chopped Strawberry Milano pieces.

Fill Cupcake Liners & Bake

Scoop batter into liners, filling only 2⁄3 full.

Bake for 18-20 minutes until cupcakes spring back when touched.

Allow to cool completely before frosting.

Make Strawberry Buttercream

Beat butter until smooth and creamy.

Gradually mix in powdered sugar, then strawberry puree and vanilla.

Mix on high speed until light and fluffy.

Assemble Your Cupcakes

Core a small hole in each cooled cupcake and insert a whole mini Milano cookie.

Top cupcakes with strawberry buttercream.

Garnish with sliced berries and Milano crumbs.

What to Serve with Strawberry Milano Cupcakes

While these cupcakes are a treat all on their own, here are some fun beverage pairings:

  • Strawberry milk – Sweet, pink strawberry milk complements all the flavors perfectly.
  • Sparkling rosé – Fizzy with subtle berry notes that won’t overpower.
  • French press coffee – Rich coffee provides an elegant contrast and caffeine boost!
  • Lemonade – Tart, sweet lemonade brightens the palate between cupcakes.
  • Hot chocolate – Because chocolate makes all things better, including these already chocolatey cupcakes!

Possible Substitutions

  • Lemon Milanos – For a sweet citrus twist
  • Vanilla Milanos – For extra vanilla flavor
  • Chocolate Chip Milanos – For loads of melty chocolate
  • Almond Cocoa Milanos – Nutty richness
  • Mint Milanos – Fresh contrast to sweet frosting


How long do the baked cupcakes last?

Store cupcakes in an airtight container for up to 5 days. Freeze unfrosted cupcakes for up to 2-3 months.

Can I use a cake mix instead?

Absolutely! Use your favorite white or yellow cake mix for an even easier shortcut version.

What tips prevent sinking Milano pieces?

Finely chopping the Milano cookies helps them incorporate rather than sinking. Also don’t overmix once they are added so they stay suspended in the batter.

How do I make a smooth frosting?

Use seedless strawberry jam or blend fresh strawberries into a puree rather than using strawberry chunks which make frosting lumpy.

Strawberry Milano Cupcakes

Prep Time20 minutes
Cook Time20 minutes
Total Time40 minutes
Course: Dessert
Cuisine: American
Keyword: cupcakes
Servings: 12 cupcakes


  • Stand mixer
  • Hand mixer
  • Mixing bowls
  • Measuring cups
  • Measuring spoons
  • Spatulas
  • Cupcake liners
  • Piping bags (optional)


For the Cupcakes:

  • 1 and 1/2 cups all-purpose flour
  • 3/4 cup granulated sugar
  • 1 and 1/2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1/2 cup unsalted butter room temperature
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1/2 cup milk
  • 1 cup fresh strawberries finely chopped

For the Strawberry Buttercream Frosting:

  • 1 cup unsalted butter softened
  • 3-4 cups powdered sugar adjust based on desired sweetness
  • 1/4 cup strawberry puree made from fresh strawberries
  • 1 teaspoon vanilla extract

For Garnish:

  • 12 slices fresh strawberries


Preheat Oven and Prepare Pan:

  • Preheat your oven to 350°F (175°C). Line a cupcake pan with paper liners.

Make the Cupcake Batter:

  • In a medium bowl, whisk together flour, baking powder, and salt.
  • In a larger bowl, cream the butter and sugar until light and fluffy.
  • Add eggs one at a time, then vanilla, mixing well after each addition.
  • Then add the dry ingredients and milk to the butter mixture, starting and ending with the dry ingredients.
  • Gently fold in the chopped strawberries.

Bake the Cupcakes:

  • Fill the cupcake liners about two-thirds full with the batter.
  • Bake for 18-20 minutes or until a toothpick inserted into the center comes out clean.
  • Allow the cupcakes to cool completely before frosting.

Prepare the Strawberry Buttercream Frosting:

  • Beat the butter until creamy.
  • Gradually add powdered sugar, then the strawberry puree and vanilla extract.
  • Beat until smooth and fluffy.

Decorate the Cupcakes:

  • Once the cupcakes are cool, frost them with the strawberry buttercream.
  • Garnish each cupcake with a slice of fresh strawberry and, if desired, a mini Milano cookie.
  • Serve and Enjoy!