Warm the milk to 110–115°F (about as warm as a hot bath — not steaming).
Sprinkle the yeast over the milk along with 1 tablespoon of sugar and whisk gently.
Let it sit for 5 minutes, or until the top looks foamy and bubbly.
If it doesn’t foam, your milk may have been too hot or too cold — start over for best results.
Mix the Dough
Add the eggs, softened butter, granulated sugar, and salt into the bowl with the yeast mixture.
Mix until mostly combined — it’s okay if the butter stays a little lumpy at this stage.
Add 3 1/2 cups of the flour and fold into the wet ingredients.
Let the dough rest for 5 minutes (this helps the flour hydrate and makes kneading easier).
Knead the Dough
Knead by hand or with a mixer for 5–7 minutes with the hook attachment, adding the last cup of flour to the dough.
The dough should become soft, smooth, and slightly tacky but not overly sticky.
If it sticks heavily to your hands, sprinkle in 1 tablespoon of flour at a time until it’s manageable.
Shape into a ball and place it back in the bowl.
First Rise
Cover the bowl with a clean towel or plastic wrap.
Let the dough rise for 30 minutes, or until noticeably puffier (it may not double yet — that’s okay).
Place the bowl somewhere warm, like on top of the oven while it preheats or near a sunny window.
Make the Mocha Filling
In a small bowl, mix the softened butter, brown sugar, blended oreos, and vanilla.
Stir until it becomes a smooth, spreadable paste.
Roll Out the Dough
Lightly flour your counter.
Roll the dough into a large rectangle (about 12×18 inches).
Spread the oreo filling evenly all over the dough, reaching all the way to the edges for even flavor.
Shape the Rolls
Starting from the long side, roll the dough tightly into a log.
Use a sharp knife or unflavored dental floss to slice into 12 large rolls.
Place the rolls into a greased 9×13-inch baking dish.
Alternatively, use a pizza or pastry cutter, to make 2 inch strips of dough, slicing vertically lengthwise, then roll each individual roll for a cleaner swirl.
Second Rise
Cover the rolls and let them rise for 20 minutes.
They should look puffier and fill more of the pan.
Cream Pour + Bake
Gently pour it over and around the rolls — this helps them bake extra soft and gooey.
Bake at 375°F for 25–30 minutes, or until the tops are lightly golden but still soft.
Don’t overbake or they’ll lose their gooey texture.
Make the Oreo Frosting
Beat the cream cheese and softened butter until creamy.
Add the powdered sugar and mix until smooth.
Add the vanilla and crushed Oreos, blending until combined.
Frost the Rolls
Spread the frosting over the warm rolls.
Top with extra crushed Oreos if desired and enjoy while warm!