Combine the warmed milk, yeast, and softened butter in a large bowl, stirring gently to combine. Let this mixture sit for 5 minutes to allow the yeast to bloom and activate—you'll notice it become slightly foamy. Add the room-temperature egg and sugar, mixing until well combined. The egg should be at room temperature to prevent shocking the yeast and ensure proper dough development. Stir in the salt and flour until a shaggy dough forms; don't overmix at this stage.

Transfer the dough from Step 1 to a lightly greased bowl, turning it to coat all sides. Cover the bowl with plastic wrap or a damp towel and let it rise at room temperature for 20 minutes—this short rise develops flavor and makes the dough easier to handle. While the dough rises, stir together the cherry filling and cornstarch in a small bowl; the cornstarch prevents the filling from leaking during baking and helps it set beautifully.

Turn the risen dough onto a lightly floured surface and knead gently for 1-2 minutes until it becomes smooth and elastic. Roll the dough into a 16x12 inch rectangle, working from the center outward to maintain an even thickness. Mix the cinnamon with 1 tablespoon of sugar from your ingredient list and sprinkle evenly over the dough, leaving a thin border around the edges. Spread the cherry filling mixture from Step 2 over the cinnamon layer, distributing it evenly so each roll gets a good amount of fruit and filling. I like to use an offset spatula for this—it helps me spread the filling smoothly without pressing it into the dough.

Starting from the long side, tightly roll the rectangle into a log, sealing the edge by pinching gently as you go. Using a sharp knife or bench scraper, cut the log into 12 equal pieces. Arrange the rolls cut-side up in a greased 9x13 inch baking dish, spacing them so they have room to rise but will still touch slightly when baked—this creates those signature attached rolls. Cover the pan loosely with plastic wrap or a damp towel and let the rolls rise for 15-20 minutes while you preheat the oven.

Preheat your oven to 375°F while the rolls rise. Bake the rolls uncovered for 25 minutes, then check them—they should be light golden on top. Continue baking for another 15-20 minutes until they're a deeper golden brown and the edges are set but the centers still feel slightly soft when gently pressed. I check at the 25-minute mark because ovens vary; you want them golden, not dark brown, as they continue to bake internally even after leaving the oven.

While the rolls bake, sift the icing sugar into a small bowl to remove any lumps, then whisk in the milk and vanilla extract until smooth and pourable. As soon as the rolls come out of the oven, drizzle the glaze generously over the warm rolls, allowing it to pool into the crevices and create that signature shiny finish. Let the rolls cool in the pan for 5 minutes before serving—this allows the glaze to set slightly while the rolls are still warm and at their most tender.