Step 1: Activate the Yeast
If using active dry yeast, combine the warm milk (110°F—test with thermometer), 1 tablespoon of the sugar, and the yeast in the bowl of your stand mixer or a large bowl. Stir gently and let sit for 5-10 minutes until foamy and bubbly. This proves your yeast is alive. If using instant yeast, you can skip this step and add yeast directly to the dry ingredients, then add warm milk when indicated.

Step 2: Make the Dough
Add the remaining sugar, softened butter, egg, egg yolk, and salt to the yeast mixture. Mix with a wooden spoon or paddle attachment on low speed until combined. Add 3½ cups of flour, one cup at a time, mixing after each addition. Once dough starts to come together, switch to the dough hook (or begin kneading by hand). Knead for 6-8 minutes on medium-low speed (or 8-10 minutes by hand) until dough is smooth, elastic, and slightly tacky but not sticky. Add remaining flour gradually only if needed—dough should be soft.

Step 3: First Rise
Shape dough into a ball and place in a large, lightly greased bowl. Turn once to coat all sides with oil. Cover with a clean kitchen towel or plastic wrap. Let rise in a warm, draft-free spot for 1-1½ hours until doubled in size. To test, gently press two fingers into the dough—if the indentation remains, it’s ready.

Step 4: Prepare the Filling
While dough rises, mix the brown sugar and cinnamon in a small bowl until well combined. Set aside. Make sure your ¼ cup butter is very soft, almost melted, so it spreads easily without tearing the dough.

Step 5: Roll Out the Dough
Once dough has doubled, punch it down gently to release air. Turn out onto a lightly floured surface. Roll into a large rectangle approximately 14×9 inches, with the long side facing you. The dough should be about ¼-inch thick. Try to keep edges as straight as possible for even rolls.

Step 6: Add the Filling
Using an offset spatula or knife, spread the softened butter evenly over the entire surface of the dough, leaving a ½-inch border along the top long edge (this helps seal the rolls). Sprinkle the cinnamon sugar mixture evenly over the buttered dough, pressing it gently into the butter so it sticks. Make sure to get cinnamon sugar all the way to the edges except for that top border.

Step 7: Roll It Up
Starting from the long edge closest to you, tightly roll the dough into a log, rolling away from yourself. Keep the roll tight and even as you go. When you reach the end, pinch the seam to seal. Position the log seam-side down.

Step 8: Cut the Rolls
Using a sharp serrated knife, dental floss, or sharp chef’s knife, cut the log into 12 equal pieces (about 1¼ inches each). For the cleanest cuts with dental floss: slide floss under the log, cross the ends over the top, and pull tight to slice through. This prevents squishing. Discard or bake the uneven end pieces for the baker’s treat!

Step 9: Second Rise
Arrange the 12 rolls cut-side up in a greased 9×13-inch baking pan, spacing them slightly apart (they’ll expand and touch as they rise). Cover with a towel and let rise in a warm place for 30-45 minutes until puffy and nearly doubled. They should look pillowy and be touching each other.

Step 10: Bake
Preheat your oven to 350°F during the last 15 minutes of rising. Once rolls are puffy, bake for 25-30 minutes until tops are golden brown and the internal temperature reaches 190°F. The center rolls should be set and cooked through. If tops brown too quickly, tent loosely with foil for the last 10 minutes.

Step 11: Make the Cream Cheese Frosting
While rolls bake, beat together the softened cream cheese and butter in a medium bowl with an electric mixer until smooth and fluffy, about 2 minutes. Add the powdered sugar, vanilla, and pinch of salt. Beat on low, then increase to medium-high and beat for 2-3 minutes until light and fluffy. Add milk or cream one tablespoon at a time until you reach your desired consistency—thicker for spreading, thinner for drizzling.

Step 12: Frost and Serve
Remove cinnamon rolls from the oven and let cool in the pan for just 5-10 minutes—you want them still quite warm. Spread the cream cheese frosting generously over the warm rolls, allowing it to melt slightly into all the nooks and crannies. Serve immediately while warm and gooey.