Reduce the apple cider. Pour 2 cups of apple cider into a small saucepan.
Simmer over medium heat until reduced to about 1/2 cup, 15–25 minutes. It should be syrupy and deeply fragrant. Cool to room temp.
You’ll use some in the dough and the rest in the glaze.
Warm the milk and proof the yeast. Warm 3/4 cup milk until just warm to the touch (about 105–110°F). Stir in 1 tablespoon sugar and 2 1/4 teaspoons active dry yeast. Let it sit 5–10 minutes until foamy.
If using instant yeast, skip the proof and mix it directly with the flour in the next step.
Mix the dough. In a large bowl, combine 3 1/2 cups all-purpose flour, 1/4 cup granulated sugar, and 1 teaspoon salt. Add the yeast mixture (or milk if using instant yeast), 1/4 cup cooled cider reduction, 2 large eggs, and 6 tablespoons softened unsalted butter. Mix until a shaggy dough forms.
Knead until smooth. Knead by hand on a lightly floured surface or with a stand mixer and dough hook for 8–10 minutes.
The dough should be soft, slightly tacky, and elastic. If very sticky, add flour 1 tablespoon at a time, but avoid making it stiff.
First rise. Place the dough in a lightly oiled bowl, cover, and let rise in a warm spot until doubled, about 60–90 minutes.
Make the filling. In a bowl, mix 3/4 cup packed brown sugar, 2 teaspoons ground cinnamon, a pinch of nutmeg (optional), and a pinch of salt. Melt 4 tablespoons unsalted butter and let it cool slightly.
Roll it out. Punch down the dough and roll it into a 12x16-inch rectangle on a lightly floured surface.
Brush evenly with the melted butter, leaving a small border on one long edge.
Add the filling. Sprinkle the cinnamon-sugar mixture over the buttered dough, pressing it lightly so it sticks.
Roll and slice. Starting from the long edge opposite the clean border, roll tightly into a log. Pinch the seam to seal. Slice into 12 equal rolls using a sharp knife or unflavored dental floss for neat cuts.
Second rise. Arrange the rolls in a greased 9x13-inch pan, leaving a little space between each.
Cover and let rise until puffy, 30–45 minutes. Preheat the oven to 350°F while they rise.
Bake. Bake for 22–28 minutes, until lightly golden on top and the centers register about 190°F. If browning too quickly, tent with foil for the last few minutes.
Make the glaze. Beat 4 ounces softened cream cheese with 1 cup powdered sugar until smooth.
Add 1–2 tablespoons of the remaining cider reduction, 1/2 teaspoon vanilla, and a splash of milk as needed until pourable. Taste and adjust sweetness or cider to your liking.
Glaze and serve. Let the rolls cool for 10 minutes, then spread with glaze while still warm so it melts into the swirls. Serve right away for maximum cozy vibes.