Start by warming your milk to about 110°F – it should feel warm but not hot when you test it with your finger, like pleasant bath water.
In a large bowl, combine 2 cups of the flour (we’ll add more later), sugar, yeast, and salt. Mix in the warm milk, melted butter (make sure it’s not too hot), and eggs until you get a wet, sticky batter.
Gradually stir in remaining flour until the dough starts pulling away from the sides of the bowl. It’ll still be slightly sticky – that’s what we want for soft rolls. Turn it onto a floured surface.
Knead for about 8-10 minutes. You’ll feel the dough transform from shaggy to smooth and elastic If it’s still super sticky, dust with a little flour as you knead.
Place the dough in a lightly greased bowl, cover with a damp cloth, and let rise in a warm spot for about 1 hour or until doubled. I like to turn my oven on for just a minute, turn it off, then use that slightly warm space.
While waiting, make your filling. Beat the softened butter until creamy, then mix in brown sugar, cocoa powder, and cinnamon until it looks like wet sand.
Once doubled, punch down the dough and roll it out on a floured surface into a 12×18 inch rectangle. Don’t worry about perfect edges – just aim for even thickness, about 1/4 inch.
Spread your chocolate filling evenly across the dough, leaving a 1/2 inch border along one long edge (this helps seal the roll). Sprinkle with mini chocolate chips.
Starting from the long edge without the border, roll the dough up tightly – like rolling a carpet. Keep it snug but don’t pull so hard that you stretch the dough. Pinch the seam to seal.
Cut into 12 even pieces using dental floss or a sharp knife (about 1.5 inches each). Place them in a greased 9×13 pan with a bit of space between each roll.
Cover and let rise again for about 30-40 minutes. They should be puffy and touching each other. Meanwhile, preheat your oven to 350°F.
Bake for 25-30 minutes until golden brown on top. To check if they’re done, gently lift the center roll – the bottom should be golden, not doughy.
For the frosting, beat cream cheese and butter until fluffy – seriously, give it a good 2-3 minutes. Add powdered sugar and cocoa powder gradually. Mix in vanilla and enough milk to make it spreadable but not runny.
Let the rolls cool for about 10 minutes before frosting – you want them warm enough to slightly melt the frosting but not hot enough to make it completely liquid.