Let Me Tell You About These Oatmeal Cream Pies

Okay, so you know those packaged oatmeal cream pies you used to sneak into your lunchbox (or maybe that was just me)? Well, I finally figured out how to make ‘em at home, and honestly, it’s a game-changer. The first time I tried these, I had flour on my shirt, cinnamon on my nose, and my dog staring at me like I’d invented a new form of magic. If you like a little cinnamon hug in your dessert, you’re in for a treat. And if your cookies aren’t quite round—welcome to the club.

Why I Keep Making These (and Probably Will Forever)

I make these when my little cousin comes round, because for some reason, he thinks they taste like “Christmas and cartoons.” My family goes crazy for this because the cookies are soft and chewy, and the cream filling’s just sweet enough (though my brother says he wishes it was ALL filling—kids, right?). Also, sometimes I make the cookies smaller so I can eat two and pretend it’s healthier. Oh, and I used to get frustrated when the cookies spread too much, but now I just sandwich more filling in there. Works out.

Here’s What You’ll Need (and Honestly, Some Swaps Are Fine)

1 cup (225g) unsalted butter, softened (I’ve used salted in a pinch—just skip the extra salt)
1 cup light brown sugar, packed (my grandmother always insisted on Domino, but the store brand is fine)
½ cup white sugar
2 large eggs (room temp, but I’ve used cold—no disasters yet)
2 teaspoons vanilla extract (sometimes I splash a little extra)
1 ½ cups all-purpose flour
1 teaspoon baking soda
1 teaspoon ground cinnamon (if you’re feeling bold, try 1 ½ tsp!)
½ teaspoon salt
3 cups old-fashioned rolled oats (quick oats work, but the texture gets a bit weird. Still edible though!)
For the filling:
- ½ cup (115g) unsalted butter, softened
- 1 ¾ cups powdered sugar (confectioners’ sugar)
- 1 tablespoon milk (or cream for extra decadence)
- 1 teaspoon vanilla extract
- Pinch of salt (optional, but I like it)

This Is How I Make Oatmeal Cream Pies (With a Couple Detours)

Preheat your oven to 350°F (180°C). Line two baking trays with parchment, or silicone baking mats if you’re fancy (I usually run out and just butter the sheet—works fine, just more washing).
In a big bowl (I use my largest because I’m messy), cream together the butter, brown sugar, and white sugar until it’s light and fluffy. This is where I usually sneak a little taste. If you’re using a stand mixer, low speed is fine. Hand mixer? Good luck to your wrist.
Crack in the eggs and pour in the vanilla—mix again. Don’t freak out if it looks a bit split at this stage. It always comes together when you add dry stuff.
In another bowl (or honestly, just a big measuring jug), whisk together the flour, baking soda, cinnamon, and salt. Dump this into the wet stuff. Mix gently, or you’ll get flour in your hair. Ask me how I know.
Fold in the oats. The dough will be thick. If your spoon stands up on its own, you’re golden. Let the dough chill in the fridge for 20 minutes if you’ve got time—it keeps the cookies from spreading too much. But sometimes I can’t be bothered and just bake straight away.
Scoop out balls of dough, about a heaping tablespoon each. Place on your trays, leaving space for spread. Press down a little with your fingers or a fork if you like thinner cookies.
Bake for 10–12 minutes, until the edges look golden and the centers are still a little soft. They’ll firm up as they cool, promise. Let them sit on the tray a few minutes before moving to a rack. (Or just eat one hot, like I do. No regrets.)
For the filling, beat softened butter with powdered sugar till fluffy—add milk, vanilla, and a pinch of salt if you like. It should be smooth, a bit fluffy. If it’s too thick, add another splash of milk. Too thin? More sugar. Very scientific, I know.
Pair off your cookies by size (or don’t, but they’ll look a bit wonky). Smear or pipe the filling onto the flat side of one; sandwich with another. Squish gently—don’t go wild, or the filling oozes everywhere.

Stuff I’ve Learned (the Hard Way)

If you overbake these, they go from chewy to, well, oat-bricks. Watch your oven like a hawk.
Using quick oats makes a softer cookie, but the texture’s kinda odd. Rolled oats are best, but hey, beggars can’t be choosers.
I thought I could freeze assembled pies, but the filling gets a bit weird. Freeze just the cookies, then fill them fresh. Lesson learned.

Variations (and One Flop)

Once, I swapped half the butter for coconut oil—tasted good, but the cookies were super fragile. Not ideal for sandwiching, but if you like coconut, it’s worth a shot.
Added mini chocolate chips to the dough once. That was a hit, actually!
On a whim, I tried adding chopped dried apricots. Did not love it. Maybe cranberries would be better? If you try, let me know!

Do You Really Need Special Equipment?

I use a stand mixer when I feel like being fancy, but really, a big bowl and strong arm do the trick. Don’t have a cookie scoop? Use two spoons, or even your hands (just wash ‘em first, obviously). If you don’t have parchment paper, just butter your baking sheet—clean up’s a bit more of a pain, but it works.

Oatmeal Cream Pies with Cinnamon Oatmeal Cookies

How Long Do They Keep? (Not Very, If You Ask My Family)

Store in an airtight container at room temperature for up to 3 days—but honestly, they usually vanish within 24 hours around here. If it’s warm, pop them in the fridge so the filling doesn’t go melty. Oh, and if you want to freeze just the cookies, they’ll keep for a month or two. I rarely have leftovers that long.

Serving These (Or, How We Eat Them)

If I’m feeling fancy, I dust the tops with a little extra powdered sugar before serving. My dad likes his with a glass of cold milk; my aunt dips hers in coffee, which sounds weird, but maybe she’s onto something. Sometimes, I even pack one in my bag for a mid-morning snack (shh, don’t tell my boss).

Pro Tips (AKA, My Whoopsie Moments)

I once tried stacking the cookies while they were warm. Big mistake. The filling melted and turned my tower into a leaning pile of goo.
Don’t rush creaming the butter and sugars—if you do, the cookies end up denser than a brick. Trust me, it’s worth taking your time.
Actually, I find it works better if you let the cookies cool completely before filling. Tried to hurry once—messy results.

FAQ (Because People Actually Ask Me These Things)

Can I make these gluten free?
Yeah, I think so! Use your favorite 1:1 gluten free flour blend and make sure your oats are certified GF. Haven’t tried it myself, but my friend swears by this recipe as a starting point.
Can I double the recipe?
Oh, for sure. Just make sure your mixer (or arms) can handle it, and bake in batches so you don’t overcrowd the tray.
Why did my cookies spread too much?
Could be warm butter, or maybe too little flour. I sometimes chill the dough for 30 min if my kitchen’s hot. Or maybe your oven runs hotter than mine (can’t trust these appliances sometimes!).
Any dairy-free filling suggestions?
Try using vegan butter and a splash of almond milk. I found Nora Cooks’ vegan frosting helpful when baking for my lactose-intolerant cousin.
Do I have to use cinnamon?
Not technically. But you’d probably miss a little of that magic. If you hate cinnamon, just skip it (or, use nutmeg—though it’s not the same, but hey, your cookies, your rules!)

By the way, if you find yourself craving more oatmeal recipes, check out Sally’s Iced Oatmeal Cookies—you might just start your own oatmeal cookie collection.

Oatmeal Cream Pies with Cinnamon Oatmeal Cookies