Step 1: Make the Dough
In the bowl of a stand mixer fitted with the dough hook, stir together the warm milk and yeast. Let it sit for 5 minutes until it looks a little foamy. (If it doesn’t foam, your yeast may be expired.)
Add the flour, eggs, cubes of butter, sugar, and salt to the bowl. Mix on low speed until the ingredients come together in a shaggy dough, about 1 minute. Increase the speed to medium-low and knead for 10 minutes, until the dough is smooth, elastic, and pulling away from the sides of the bowl.
If the dough is still sticky after 5 minutes, add more flour 1 tablespoon at a time until it’s just tacky and manageable and not sticking to the sides of the bowl.
Lightly grease a large bowl with olive oil. Place the dough in the bowl, turn it once to coat, cover with a clean towel, and let it rise in a warm spot for 1 to 1 1/2 hours, until puffy. It doesn’t need to double, just give it room to bloom. Alternately, you can leave the dough to rise in the refrigerator overnight and let come to room temperature for 45 minutes before assembling.
Step 2: Make the Filling
In a medium bowl, mix together the soft butter, brown sugar, cinnamon, cocoa, and salt with a fork until it forms a thick, spreadable paste. Make sure there’s no loose sugar, no dry cinnamon, we want the spread smooth and slatherable.
Step 3: Roll and Fill
Lightly flour your work surface and rolling pin. Gently punch down the dough and roll it into a 12×24-inch rectangle, about 1/4 inch thick. Drop the filling in small bits across the surface, then spread it evenly with a small offset spatula, leaving a 1/2-inch border.
Starting with the long side closest to you, roll the dough tightly into a log. Pinch the seam closed and place the log seam-side down.
Use a length of unflavored dental floss to slice the log into 12 even rolls.
Step 4: Proof + Bake
Grease a 9×13-inch baking dish and line the bottom with parchment paper. Spray the parchment and sides again.
Place the rolls in the pan, cut-side up, spaced evenly. Lightly spray a piece of plastic wrap, cover the pan spray-side down, and let the rolls rise for 1 to 1 1/2 hours, until just touching.
Preheat the oven to 375°F. Bake for 20 to 25 minutes, until golden, puffed, and the center registers 200°F. Let them cool slightly while you make the frosting.
Step 5: Frost Like You Mean It
In the bowl of a stand mixer fitted with the paddle attachment (or in a medium bowl with hand beaters), beat together the cream cheese, butter, vanilla, lemon, and salt until smooth and light, about 2 minutes. Add the powdered sugar and beat on low to combine, then crank it up to medium-high until fluffy and spreadable.
Spread the frosting generously over the warm rolls and let it melt into every swirl and corner. Let them cool for 10 more minutes (if you can wait) before serving.
