Whisk the warm milk, 2 Tablespoons sugar, and the yeast together in the bowl of your stand mixer fitted with a dough hook attachment. Cover and allow mixture to sit for about 5 minutes or until foamy on top.

Add the remaining sugar, the butter, orange juice, orange zest, eggs, salt, and 1 cup (about 130g) of flour and beat on medium speed for 1 minute. Stop and scrape down the sides of the bowl. Add 3 more cups (about 400g) flour and beat on low speed until a soft dough forms and pulls away from the sides of the bowl.

Keep the dough in the mixer and beat on low speed for an additional 6–8 full minutes; or knead by hand on a lightly floured surface for 6–8 full minutes.

Lightly grease a large bowl with oil or nonstick spray. Place the dough in the bowl, turning it to coat all sides in the oil. Cover the bowl and allow the dough to rise in a relatively warm environment for 1.5–2 hours or until about double in size.

Grease the bottom and sides of a metal or glass 9×13-inch baking dish, or line with parchment paper.

Punch down the dough to release the air. Place dough on a lightly floured work surface and roll dough into a 10×16-inch rectangle.

Spread the softened butter all over the dough. Mix the remaining filling ingredients together until the zest has moistened it, then sprinkle evenly on top of the butter. Tightly roll up the dough to form a 16-inch-long log. Cut into 12 even rolls, between 1–1.5 inches wide each. Arrange in the prepared baking pan.

Cover the rolls tightly and allow to rise until puffy, about 30–45 minutes.

Preheat the oven to 350°F (177°C). Bake rolls for about 25–28 minutes or until they are lightly browned on top.

In a small bowl or liquid measuring cup, whisk confectioners’ sugar, orange juice, and vanilla extract together until combined and smooth. Drizzle over the warm rolls and serve immediately.