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Homemade Oatmeal Cream Pie Cookies

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The BEST Homemade Oatmeal Cream Pie Cookies! I tested this recipe to get it just right! Soft & chewy oatmeal cookies and a light cream filling.

For years I have tried to find a perfect Oatmeal Cream Pie Cookie. There are some amazing recipes out there that have perfectly chewy oatmeal cookies, but then they use a buttercream or other rich frosting that is just too heavy! And there are some that get the light creamy filling down but the cookie it too tough or thick. My kids requested I work on this recipe so I made it my goal to figure it out and get it right!

First off, the chewy oatmeal cookie. The cookie needs to be thin and chewy, with lots of oats, and a deeper flavor than a basic oatmeal cookie. This requires 2 things: a little molasses & cinnamon in the cookie for that depth of flavor and rich color, and a very high ratio of butter to flour. This cookie dough is very wet and that’s how it should be! You will make the cookie dough up and then scoop it into small cookie dough balls. The dough will spread a lot when baking so the balls must be small! (1 tablespoon). Then you will freeze the dough for a short time to help set the dough and let the flavors come together, then bake. After you bake the cookies, you will set them aside to cool while you make the filling.

Second, the light and creamy filling. Many recipes I found used buttercream or some variation of it – no! This classic oatmeal cream pie needs a light, white, creamy, and slightly airy filling. To achieve this consistency I used a combination of shortening and marshmallow cream (mixed with powdered sugar and vanilla). This creates an extremely light and shelf-stable cream that is the perfect replica for an oatmeal cream pie.

Lastly, assembling the cookie. To get that perfect oatmeal cream pie look, be sure to pipe the cream filling onto the cookies. You will pipe only into the center of a cookie, then use the top cookie to press the filling out evenly to the sides. You could technically use a knife to spread it on, but it won’t have the same look as a traditional oatmeal cream pie. Even if you only have a ziploc bag with the edge cut off, try to pipe this filling on. It looks great!

The best part about these cookies is the shelf-stable cream filling, so you can eat them right away or save to transfer to a party or gathering. The rich and flavorful soft oat cookie is the perfect balance to the light cream filling.

Homemade Oatmeal Cream Pie Cookies

The BEST Homemade Oatmeal Cream Pie Cookies! I tested this recipe to get it just right! Soft & chewy oatmeal cookies and a light cream filling.
This recipe makes about 16-18 completed cream pies (32 total cookies before assembly).
Plum Street Collective
Prep Time 10 minutes
Cook Time 10 minutes
Freezer Time 15 minutes
Total Time 35 minutes
Serving Size 16


Oatmeal Cookies

  • 1/4 cup unsalted butter, softened
  • 3/4 cup shortening
  • 3/4 cup brown sugar
  • 1/2 cup white sugar
  • 2 eggs
  • 1 tablespoon molasses
  • 2 teaspoons vanilla extract
  • 2 cups old-fashioned oats
  • 1 ¾ cup flour
  • 1/2 teaspoon cinnamon
  • 1/2 teaspoon salt
  • 1 teaspoon baking soda

Cream Filling

  • 1⅓ cup powdered sugar
  • cup shortening
  • 2 jars marshmallow cream (7 oz. jars)
  • 2 teaspoons vanilla
  • 1/4 teaspoon salt
  • 1 tablespoon very hot water


Oatmeal Cookies

  • In a stand mixer, fitted with the paddle attachment, add the softened butter and the shortening. (Can also use a hand mixer.)
    Mix on medium speed until creamed together well, about 1 minute.
  • Add in the white sugar and brown sugar and cream again until well mixed.
  • Next, add in the eggs, molasses and vanilla. Mix well, scraping down the bowl as needed.
  • In a separate bowl combine the dry ingredients (oats, flour, cinnamon, salt, and baking soda). Mix well.
  • Slowly add the combined dry ingredients to the wet mixture. Mix on medium speed until well incorporated.
  • Line a large baking sheet with parchment paper.
    Using a 1 tablespoon cookie scoop, scoop the dough onto the parchment-lined baking sheet.
    Chill the dough in the freezer for 15-20 minutes.
  • Meanwhile, preheat the oven to 330°F.
  • Once you remove the dough from the freezer, place dough balls on a new parchment-lined baking sheet about 3-4 inches apart from each other (they will spread).
  • Bake in preheated oven for 9-12 minutes, until the edges are slightly golden and the middle is still soft.
    Let the cookies rest and cool on the pan they baked in. This will help the bottoms set.

Cream Filling

  • In a large mixer fitted with the paddle attachment (or in a large bowl with a handheld mixer), Add the shortening and marshmallow cream.
    Mix at medium speed until well incorporated.
  • Next add the powdered sugar and vanilla and mix until combined.
  • Lastly, in a separate cup or bowl, add the salt plus the 1 tablespoon of very very hot water (I used our tap water on the hottest setting for this).
    Mix the hot water and salt until the salt is dissolved, and then pour the mixture into the cream mixture. Mix well on medium speed until combined.
  • Add the cream filling to a piping bag or ziploc bag.
  • Once the cookies have cooled, pipe a small amount of frosting into the center of each cookie. Then use another cookie to press down on the filling and help it spread to the edges of the cookie, making a cookie sandwich.
  • Continue piping and filling all the cookies, and enjoy!
    (These cookies can be stored in an air-tight container at room temperature for a week).

I hope you get a chance to try out these Homemade Oatmeal Cream Pie Cookies – and check out my other cookie recipes here. Tag me with photos if you make these @plumstreetcollective on Instagram. Thanks for reading!

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