In a microwave-safe mug, warm milk for about 20 seconds until it’s lukewarm, not hot (aim for about 105 to 115 degrees Fahrenheit). Stir in the active dry yeast and allow it to sit for 10 to 15 minutes until the top of the mixture is foamy. This shows that your yeast is active and ready to work its magic.
In a medium bowl, whisk together the foamy yeast mixture, melted butter, granulated sugar, egg yolk, and salt. Ensure everything is mixed well before moving to the next step.
Add the all-purpose flour a third at a time, mixing with a spoon until you form a thick and sticky dough. Don’t worry if it seems a bit rough; it will come together shortly.
Dump the mixture onto a well-floured work surface. Knead the dough gently until it’s no longer sticky and forms a ball, which should take about 10 gentle folds. This process develops the gluten, making your rolls fluffy.
Place the dough into a greased bowl, cover it with a towel, and let it rise in a warm place for about an hour, or until it has doubled in size.
While the dough rises, lightly grease your 6 to 7-inch baking dish. Once the dough has risen, turn it out onto a lightly floured surface, gently squish and stretch it into an oblong shape.
Using a floured rolling pin, roll the dough out to about 5 by 15 inches, making sure to keep it as rectangular as possible for even filling distribution.
Spread the remaining butter over the rolled-out dough, and then top it with a mixture of brown sugar and cinnamon. Sprinkle the chocolate chips evenly across the filling.
Starting from the short side, carefully roll the dough into a tight log. Use a serrated knife to cut the roll into quarters, making sure to be gentle so the filling doesn’t spill out.
Place the rolls into your prepared baking dish. If you’re making these rolls overnight, cover them tightly with plastic wrap and place in the fridge. If not, allow the rolls to rise again in a warm place for about 30 minutes.
Preheat your oven to 400 degrees Fahrenheit. Once the rolls have risen, bake them for about 12 to 15 minutes until the tops are golden and the centers are cooked through. If the tops brown too quickly, cover them with foil.
While the rolls are baking, prepare the espresso glaze by whisking together the sifted powdered sugar, espresso powder, vanilla extract, and a pinch of salt in a medium bowl. Add in the milk until you reach your desired consistency.
As soon as the rolls are done baking, spoon the glaze over the warm rolls. Serve and enjoy the delightful combination of chocolate and cinnamon!
