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).

Prep Time 10

Cook Time 10

Freezer Time 15

Total Time 35

Servings 16

Author Plum Street Collective

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.
Note: the cookie dough will be much thinner than typical cookie dough; this is what allows it to bake into thin chewy oatmeal cookies.
Line a large baking sheet with parchment paper.
Using a 1-2 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).
Using the back of a spatula or your hand, slightly press each cookie dough ball down, so it flattens a little bit before baking. This will help the cookie to spread wider while baking.
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.

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).