These Homemade Oatmeal Cream Pies are so much better than their store-bought counterparts and are made completely from scratch! Plus, they can be made ahead and are freezer-friendly! An absolutely delicious dessert to feed a crowd!
Preheat oven to 350 degrees F. Line three baking sheets with parchment paper, set aside.
In a small bowl, combine flour, salt, baking soda, and cinnamon, set aside
In the bowl of your standing mixer, cream together butter & sugars.
Add molasses, vanilla, and eggs and beat until well combined.
Add flour mixture and beat until completely combined.
Add in the oats and cinnamon chips and mix on low speed until just combined.
Drop 1 TBS portions of dough onto your prepared baking sheets. It’s important to make sure they’re all the same size and shape to make it easier to form sandwiches!
Bake at 350°F for 10-12 minutes, or until the center is just set.
Remove from the oven. You will notice that the cookies flatten out a LOT and usually run into each other. Immediately use a spatula to gently separate & create space between the cookies if they baked together.
Let your cookies cool on the pan for 5-10 minutes.
When your cookies are mostly cooled, move onto a wire rack to cool completely.
While cookies are baking, make filling:
Beat together ½ cup butter and powdered sugar slowly until combined
Add vanilla and whipping cream, beat until combined.
After cookies have cooled spread 1 TBS filling between two cookies, putting the bottom sides together.
The cookies flatten a LOT while baking. That is normal! Bake only until they just look set. Please do not overbake or they will lose their chewy soft texture! If you want perfectly round cookies I recommend only baking 6 per sheet. These freeze exceptionally well! Store in an airtight container separated by wax paper in the freezer!