
Moist chocolate cake soaked with Oreo pudding and crowned with billowy whipped cream makes this crowd pleasing dessert irresistibly creamy and celebratory.

When I bring this to family dinners, I barely set the pan down before someone asks for a corner piece. The pudding pour always gets attention, and kids love to help poke the holes. My small discovery is to align the holes with where you plan to cut, so every square shows those pretty cream filled tunnels.
My favorite part is lifting the first square and seeing every tunnel striped with cookies and cream. On my nephew’s birthday, he asked for the piece with the most crumbs, then quietly came back for seconds. I have learned that a gentle tap on the counter after pouring the pudding helps it settle into every channel, creating those striking layers that make people smile even before the first bite.
Allow the cake to chill until the pudding is fully set, then cover the pan tightly with plastic wrap or a fitted lid. Keep refrigerated for up to three days for best texture. For longer storage, slice the cake into squares, place them in airtight containers, and freeze for up to one month. Thaw slices overnight in the refrigerator and serve chilled. Avoid leaving the cake at room temperature for more than one hour, especially in warm kitchens. If the whipped cream softens, a brief chill restores clean edges. Do not freeze the cake uncovered, as the whipped topping can pick up off flavors and form ice crystals.
If you prefer a lighter crumb, swap half of the melted butter with neutral oil, keeping the total fat at one half cup. No buttermilk on hand, use one cup milk mixed with one tablespoon white vinegar and let stand five minutes. For the pudding layer, vanilla instant pudding with one half cup finely crushed Oreo crumbs makes a good alternative to Oreo branded mix. Stabilized whipped cream works if you need a longer hold time, or use thawed whipped topping for convenience. Gluten free chocolate cake mix can be used with care, though texture will be slightly more delicate. Lactose free whole milk can set instant pudding, but always check packaging for compatibility.
Cut the cake into neat squares and serve chilled for clean layers and tidy edges. For a party platter, add a small dollop of whipped cream on each piece and tuck a mini Oreo or a chocolate shaving on top. A drizzle of warm chocolate sauce or a spoonful of crushed berries makes an elegant twist. This pairs nicely with coffee, cold milk, or vanilla iced lattes. For birthdays, scatter rainbow sprinkles over the cream. For a dinner party, finish with a pinch of flaky salt to sharpen the cocoa notes.
Poke cakes became popular in American home kitchens in the mid twentieth century as a playful way to combine convenience products with clever technique. The method of poking warm or cooled cakes and pouring in something flavorful allowed home bakers to create layered textures without special tools. Cookies and cream as a flavor took off later, inspired by the nostalgia of sandwich cookies and the popularity of cookies and cream ice cream. This Oreo themed version blends those traditions, giving you a simple batter, a creamy filling, and a light topping that feels both retro and modern.
In summer, serve this cake well chilled with fresh raspberries for a bright, tart contrast. Around the holidays, add a quarter teaspoon peppermint extract to the whipped cream and garnish with crushed peppermint candies. For fall gatherings, scatter mini chocolate chips alongside the cookie crumbs for extra texture. Spring parties benefit from a light dusting of cocoa and a few edible flowers for a soft look. If you want a birthday twist, stir colorful sprinkles into the whipped cream just before spreading for a cheerful confetti finish.
Bake and poke the cake a day in advance, fill with pudding, and chill overnight for the cleanest cuts. Whip the cream the day you plan to serve, which takes only a few minutes and gives the topping its freshest taste. Portion leftovers into individual containers for easy lunchbox treats. When transporting, keep the cake cold with freezer packs and a snug lid to protect the whipped topping. If you need to hold the cake longer for an event, cover and refrigerate, then add a final sprinkle of cookie crumbs just before serving to keep the texture crisp.
There is a special joy in bringing a chilled pan of cookies and cream delight to the table and watching the first slice reveal those creamy tunnels. Make it once, and you will keep finding excuses to make it again, because it is that simple and that good.
This Creamy Oreo Poke Cake recipe makes perfectly juicy, tender, and flavorful steak every time! Serve with potatoes and a side salad for an unforgettable dinner in under 30 minutes.

Preheat oven to 350 degrees Fahrenheit. Grease a 9 by 13 inch baking pan with nonstick spray or a thin coat of shortening.
In a large bowl, combine cake mix, instant chocolate pudding, eggs, melted butter, buttermilk, and vanilla. Beat with a hand mixer on medium for 2 to 3 minutes until smooth and thick.
Spread batter into the pan and bake 25 to 30 minutes until a toothpick inserted in the center comes out clean.
Cool on a rack for about 30 minutes. Using the end of a wooden spoon, poke holes 3/4 inch apart across the surface.
Whisk Oreo pudding with cold whole milk for 1 minute until smooth. Immediately pour over the cake, filling holes. Tap pan gently and spread remaining pudding evenly.
Chill the cake uncovered 1 to 2 hours. Whip heavy cream with powdered sugar to stiff peaks. Sprinkle some crushed cookies, spread whipped cream, and finish with remaining crumbs.
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