Amazing Cinnamon Rolls

This is a serious cinnamon roll project that yields a generous 40 rolls. The dough is enriched with milk and shortening, kneaded until elastic, and given a full hour to double. That long rise is non-negotiable. Underproofed dough produces dense rolls that bake into bread bricks rather than pillowy spirals.

The filling deviates from standard supermarket cinnamon rolls in two important ways. First, chopped walnuts add crunch against the soft dough. Second, raisins (or your dried fruit of choice) provide chewy bursts of sweetness throughout. The brown sugar plus cinnamon ratio (a generous ¾ cup brown sugar to just 1.5 teaspoons cinnamon) lets the caramel-molasses notes lead, which is the right balance.

The icing is the real signature. Orange juice (not just milk) thins the powdered sugar, vanilla AND almond extracts together give complex aromatic depth, and a quarter cup of butter melts in for body. Drizzle while the rolls are still hot so the icing soaks into the warm crumb.

40 rolls is a lot. Freeze half unbaked after cutting, then thaw, proof, and bake for fresh rolls on demand.

Pro Tips

• Slice the rolled log with unflavored dental floss instead of a knife. Floss cuts cleanly without compressing the spiral.
• Tuck the loose end of each roll under to prevent it unspooling during the bake.
• The second proof (after slicing) is essential. Skipping this step gives you tight, tough rolls.
• Bake until the centers spring back when gently pressed and the tops are deep golden, not just lightly browned.

Variations

• Sub pecans for walnuts and dried cranberries for raisins for a more festive holiday version.
• Use lemon juice in the icing instead of orange for a brighter citrus finish.
• Swap shortening for melted butter in the dough for a richer flavor.