Oreo Cinnamon Rolls

My highest culinary hill to die on — besides that I will fight anyone who ruins butter — is that Oreo Cinnamon Rolls are a mood and deserve an apology tour.

Look, if you once tried to make cinnamon rolls from a shaky Pinterest post and ended up with doughy sad pancakes, I see you and I raise you an Oreo. Also, if you want more glaze-committed chaos, check out my beloved sourdough cinnamon rolls guide for jealousy fuel.

The Thanksgiving that escalated (and why I still cook with band-aids)

One year I decided Thanksgiving needed spectacle. Not just turkey spectacle (we outsourced that to Uncle Pete — bless his smoke ring) but dessert spectacle: cinnamon rolls with an Oreo tantrum inside. I was young, hubristic, and armed with exactly three spatulas and zero humility. Long story short: flour avalanche, dog stole a roll, I cried. Also, my cousin filmed the aftermath for posterity. (It’s now a family rite. Send help.)

There was also the lemon bars disaster of 2019 (never forget) but the Oreo rolls? They survived, they thrived, they became the thing people ask me to bring when they want chaos disguised as comfort.

Before you roll your eyes: here’s why you should actually make these

ANYWAY, before I emotionally relive the entire event and my dignity evaporates like sugar on a hot pan — these are not your grandmother’s dainty rolls (unless your grandma is secretly a cookie hoarder from Trader Joe’s). They are pillowy, a little gritty with cookie crumbs, and will make people fight for the last one in a way that is unsettling and deeply satisfying.

All the goods you’ll need (plus my grocery gripes)

• 2 cups all-purpose flour
• 1/2 cup granulated sugar
• 1 packet active dry yeast
• 1/2 cup milk, warm
• 1/4 cup unsalted butter, melted
• 1 large egg
• 1 teaspoon vanilla extract
• 1/2 teaspoon salt
• 1/2 cup Oreo cookies, crushed
• 1/4 cup unsweetened cocoa powder
• 1 teaspoon ground cinnamon
• 1/2 cup cream cheese, softened
• 1/4 cup powdered sugar
• 1/4 cup crushed Oreo cookies for topping

Mini-rant: You do NOT need artisanal black salt from a Himalayan glacier; regular stuff from Aldi or Trader Joe’s is fine (and probably more fun—Trader Joe’s pomegranate molasses is my emotional support aisle). If you’re feeling extra, use the good butter. If you’re broke and brave, margarine will not forgive you but life goes on. Also, if you’ve never used Oreo as a filling replacement for all self-control, bless.

Cooking Unit Converter — because measuring like a robot is necessary

If you need to convert cups to grams mid-cry, this nifty tool will save your sanity.

Technique, in my scatterbrained but practical way (and the actual steps I Learned the hard way)

I will not pretend I invented dough therapy, but here’s what I learned after nearly gluing my hands together with overworked gluten: be gentle, let yeast nap, and NEVER rush the second rise (that’s where the magic forgives you). Also — roll tight like you’re tucking yourself into bed after a long, dramatic day.

1. In a large bowl, combine warm milk, sugar, and yeast. Let it sit for 5-10 minutes until bubbly.
2. Add melted butter, egg, vanilla extract, and salt to the yeast mixture. Mix well.
3. Gradually add the flour and knead until a soft dough forms. Let it rise for about 1 hour, or until doubled in size.
4. In a separate bowl, mix together cocoa powder, cinnamon, and crushed Oreos for the filling.
5. Roll out the dough into a rectangle, spread the filling evenly, and roll it tightly.
6. Cut into rolls and place them in a greased baking dish. Let them rise for another 30 minutes.
7. Preheat the oven to 350°F (175°C) and bake rolls for about 20-25 minutes or until golden brown.
8. For the glaze, mix cream cheese and powdered sugar until smooth. Spread over warm rolls and top with additional crushed Oreos. Serve warm.

Tip that took me three tries and a sob: if your filling slides out like it’s fleeing responsibility, chill the rolled log for 15 minutes before slicing. That saved me from a meltdown and a sticky floor.

Also, if you’re distracted by other brunch projects (I emphatically recommend fewer projects), peep some wild air-fryer spin-offs like this air-fryer cheeseburger egg rolls riff for inspiration and regret-management.

Why this matters to me (and why it should to you too)

Food is how my family says “I love you” without actually saying it — through burnt pies, over-salted soups, and cookies stolen at midnight. Baking is memory-making; the smell of cocoa and yeast takes me back to a tiny kitchen with a radio on and my mom swearing softly when the timer didn’t go off. It’s tradition, identity, and sometimes therapy, in sticky, delicious form.

Tiny anecdote: the neighbor who stole my roll and apologized with jam

My neighbor once confessed she took a roll out of the Tupperware, left a note that said “Sorry, it was an emergency,” and returned it with homemade jam. I keep the note. It’s framed. It’s basically art.

Frequently Asked Questions: Chaos Edition

Okay, I’ll stop now — except: make them, serve them warm, and if someone dares to say “it’s too sweet,” hand them another and watch their face change. Trust me.