Homemade Oatmeal Cream Pies

These homemade oatmeal cream pie cookies are incredibly chewy with rich notes of molasses, brown sugar and cinnamon. The creamy filling has a touch of cream cheese, making it lightly sweet and irresistible when sandwiched between the oatmeal cookies.

For the Oatmeal Cookies:
1 cup 226g unsalted butter, softened
1 cup 200g brown sugar, packed
1/2 cup 100g granulated sugar
1 tablespoon molasses
2 teaspoons vanilla extract
2 large eggs
2 cups 250g all-purpose flour
1/2 teaspoon ground cinnamon
1 teaspoon baking soda
1/4 teaspoon salt
3 cups quick oats
For the Cream Filling:
3/4 cup 168g unsalted butter, softened
2 oz 57g full-fat cream cheese, brick style
3-4 cups 330-440g powdered sugar
1 teaspoon vanilla extract
1/4 teaspoon salt
1 tablespoon cream if needed
For the Oatmeal Cookies:
Preheat oven to 350°F (180°C). Line baking sheets with silicone mats or parchment paper.
In a large bowl, beat the butter, brown sugar and granulated sugar until fluffy.
Mix in the molasses, vanilla and eggs until creamy.
Turn off mixer and add in the flour, cinnamon, baking soda and salt. Stir by hand initially to avoid flour flying out, then beat on low until incorporated.
Stir in the quick oats.
Scoop dough by 1 to 1.5 tablespoon amounts and place 2 inches apart on prepared baking sheets.
Bake one sheet at a time for 9-11 minutes, until tops look set.
Cool on baking sheet for 10 minutes, then transfer to a wire rack to cool completely.
For the Cream Filling:
Beat the butter until fluffy in a large bowl.
Beat in the chopped cream cheese until combined.
Add in 1 1/2 cups powdered sugar, vanilla and salt. Start mixing on low, then increase to medium until incorporated.
Beat in remaining powdered sugar 1/2 cup at a time until desired sweetness. If too thick, beat in 1 tbsp cream.
To Assemble:
Spread 1-1.5 tbsp of cream filling on the bottom of one cooled cookie.
Sandwich together with a second cookie, bottom facing down.
For smaller batch, recipe can be halved.
Honey can substitute for molasses if needed.
Be sure to measure flour correctly to avoid dry cookies.
Old-fashioned oats can be used instead of quick oats, but texture will be less chewy.
Cream cheese can be replaced with more butter in the filling if desired.
Make-ahead: Bake cookies 1-2 days in advance and store at room temp until assembling. Or freeze cookies for up to 2 months.
Storage: Keep assembled pies in an airtight container at room temp for 3 days or refrigerated for up to 5 days.