Combine yeast and water*5: stir together yeast and lukewarm water in the bottom of stand mixer’s bowl (a hand mixer won’t work for this dough). Allow to sit for 5 minutes while you measure out remaining ingredients (this helps the yeast start to activate and dissolve).
Stir in egg: after the 5 minutes is up, add the egg to your bowl and blend with the water/yeast mixture.
Add dries and butter, then mix on low to combine: add dry ingredients and soft butter cut into tablespoons into your bowl with the yeast. Using a dough hook, run mixer on the lowest setting (usually “stir”) until all ingredients are roughly combined, scraping bowl as needed to help any dry pockets blend in (about 1-2 minutes).*6
“Knead” on medium-low speed until elastic: with mixer on 2/10, allow the dough to mix for 2 minutes so it can start forming into a single, sticky mass. After that, raise the speed to 3 or 4/10 (no higher than 4/10)*7 and allow dough to mix for 8-10 minutes, checking it often. You’ll know it’s ready when it has formed into a single smooth mass, and it springs back with a little elasticity when you pull on it. You’ll also likely hear it start “slapping” against the side of the bowl when it’s ready, and you should be able to stretch it into a thin “window pane” (see photos in post for more detail!).*8
Allow dough to rise: remove dough from mixing bowl and form loosely into a ball. Lightly grease mixing bowl with baking spray, then drop dough back into bowl, rolling it around to lightly grease it on all sides (this prevents a skin from forming). Loosely cover bowl with a dish towel or plastic wrap (that’s not sealed), and allow dough to rise in a warm place for about 1 ½ hours until doubled in size, soft, and very puffy. When it’s ready, an indent should remain with no bounce back when you press your finger gently into the dough (see photos in post for more detail!).
TO ASSEMBLE THE ROLLS:
Make the filling: near the end of the rise time, combine sugar and cinnamon, or sugar and cocoa powder.*4
Knock it down and roll it out: working on a lightly floured surface, dump your risen dough out onto your surface, then press it down with your hands to deflate it and release the gases. Re-flour your surface as needed and roll dough into a 14” square.
Butter the Dough: spread softened butter in a thin layer over the entire surface of the dough, but leave a ½" border along one edge to use as a seal (if butter isn’t really soft, microwave it in 7 second intervals at 20% power until it’s almost melting, otherwise it may tear your dough when you spread it).
Add filling: sprinkle buttered dough generously with the cinnamon or cocoa sugar mixture to fully cover the butter, using your hand to spread it into an even-ish layer. Then, sprinkle crushed Oreos on top to evenly distribute them across the surface of the dough (make sure they’re fairly well crushed so they roll up nicely in this soft dough). Gently press them into the dough by hand to help them stick.
Roll it up: starting with the edge opposite of your clean “seal” edge, carefully roll dough in a tight log from one end to the other (do your best to keep your roll tight, but know the dough will be very soft, so don’t worry if the roll isn’t perfect). Once your roll reaches the clean edge, use your fingers to firmly pinch the seam together and seal your log up well.
Slice off the rolls: using a sharp knife, and a “sawing” not “crushing” motion, gently slice off your rolls until you have 9 equal rolls, about 1.5” wide each.
Pan them up: space them out evenly in a lightly greased 8” round pan, with one in the center, and the others in a ring around it, being sure to place the prettier side up.*9 (Don’t worry if the rolls aren’t touching - they’ll expand during both the rise and bake.)
Allow to rise again: place a lightly greased piece of plastic wrap loosely over your pan, and allow the rolls to rise about an hour in a warm place until they’re puffy, touching each other, and the dough again feels very soft and holds an indent when gently pressed. Near the end of the rise time, preheat oven to 350°F.
Bake ‘em: remove the plastic wrap and bake the buns on the middle rack of the oven for 26-30 minutes until they are golden brown. (An instant read thermometer will register 190°F+ when inserted into the center of the rolls when they're ready.) If the buns start to get too brown on top, tent them with a piece of aluminum foil for the remainder of the bake time.
Cool ‘em off a bit: once rolls are baked, allow them to cool in the pan on a wire rack for 15-20 minutes while you prepare the icing.
TO MAKE THE ICING:
Combine butter and cream cheese*10: place softened butter and cream cheese in a small mixing bowl. Beat together until smooth and fully combined by hand or with a hand mixer, until no cream cheese chunks remain (a hand mixer will give you a smoother glaze here).
Mix in the powdered sugar: add in the sifted powdered sugar, and blend until fully combined and smooth.
Blend in the milk and vanilla: add the milk and vanilla extract, and blend until smooth and fluffy again.
Spread, slice and enjoy! Spread icing on warm (but not super hot) rolls, right in their pan. Sprinkle with crushed Oreos on top for a final garnish, then tear off a roll and enjoy a perfectly warm and messy cookies and cream treat!
*1Lukewarm water: the best way to ensure the right temp of water is to use an instant-read thermometer (we’re going for 75-85°F in this recipe), but if you don’t have one available, simply use your best judgement to feel when the water is “lukewarm” but not “hot.”If the water is too hot or too cold, it will negatively effect the yeast and your rise.
*2Active dry yeast, not instant/rapid! For this recipe we want to use “active dry” yeast, bulk red yeast or bulk gold yeast, because they're all designed for the 2-rise process we’re using here. Rapid/Instant yeast is only designed to rise once, and likely will lead to a less risen, and less flavorful roll.
*3Room temperature egg hack: if you need to get your egg to room temp in a hurry, simply submerge it whole in a large container of warm water for 10-15 minutes until it’s warmed up and ready to go.
*4Cinnamon or cocoa? The option of what you mix into your filling is really up to whatever sounds good to you.I personally love black cocoa, which is what gives Oreo’s their distinctively un-sweet “chocolate” flavor.But if you don’t have any available or if you actually want some cinnamon in there with that Oreo flavor, feel free to use either a regular cocoa or ground cinnamon instead for your filling.
*5Not up for making the dough from scratch? If you’d really love to try this recipe, but homemade brioche dough is just a bit too intimidating, you can use this Hot Roll Mix as a relatively quick and easier alternative.If you’d like to use a refrigerated or frozen dough, you’re welcome to experiment, but I personally can’t recommend those here as they’ll vary greatly in flavor and performance, so I find it safer to stick with a scratch-based, predictable dough.
*6Kneading Options:I highly recommend using a stand mixer for this recipe as brioche is both very messy and rather difficult to make by hand unless you’re an experienced bread maker. But if you’d like to try it by hand, know you may need to knead the dough for 20+ minutes to reach full development. Alternatively, you can knead this dough in a bread machine. To make in a bread machine, “bloom” yeast by completing the first step, then add all remaining dough ingredients, including butter, to the mixing bin and run it on the “dough” cycle (not the bake).Once the dough cycle is complete, continue on with the recipe from assembly step 1.
*7Keep the mixer at 4/10 at the most! Don’t turn the mixer up past 4 or walk away from your dough for very long because it can over-mix very easily and there’s no going back from that unfortunately.
*8Sticky or Stiff Dough: if dough is extra sticky after 5 minutes of kneading, you can add flour, a tablespoon at a time, as needed. If it’s really dry and won’t grab the hook at all, you can splash water on it 1-2 teaspoons at a time, as needed, just until it gets a little tackiness to it. Just be careful not to overdo it with either addition!
*9Pan alternative: you can also use an 8” square pan, but I prefer the look of these rolls in a round pan if you have it available.
*10Icing-palooza: I love a lot of icing on my cinnamon rolls so you’ll find this is a very generous amount for a modest pan of rolls.Feel free to only use a portion of the icing, or even half the recipe if you'd only like a little glaze on your Oreo rolls.