For dough: In a 1-cup glass measuring cup, stir together ¼ cup water, yeast, 1 teaspoon (4 grams) granulated sugar; let stand for 5 minutes.
In the bowl of a stand mixer fitted with the paddle attachment, beat butter at medium speed until creamy. Gradually add salt and remaining 1/2 cup (93 grams) granulated sugar until light and fluffy. Add eggs, milk, and lemon juice, beating until combined. Stir in yeast mixture. Gradually add flour to butter mixture, beating at low speed until well combined, about 2 minutes.
On a lightly floured surface, turn out dough, and knead for 5 minutes. Spray a large bowl with cooking spray. Place dough in bowl, turning to grease top. Cover and let stand in a warm, draft-free place (85°) until doubled in size, about 1 hour and 30 minutes.
For cherry filling: In a medium saucepan, combine cherries, granulated sugar, and cornstarch. Cook over medium heat, stirring constantly, until bubbly and thickened, 3 to 4 minutes. Remove from heat, and stir in preserves. Let cool completely.
Grease 2 (9-inch) cast-iron skillets.
Lightly punch down dough. On a lightly floured surface, roll dough into a 14x10-inch rectangle. Spread cherry mixture over dough. Starting at one long side, roll up dough, jelly-roll style, and press edge to seal. Slice into 10 rolls, and place into prepared pans. Cover and let stand in a warm, draft-free place (85°) until doubled in size, about 45 minutes.
Preheat oven to 350°. Bake, uncovered, until golden brown, about 30 minutes. Let cool in pans for 5 minutes.
For glaze: In a small bowl, combine confectioners sugar, cherry juice, and butter. Brush over hot rolls. Let cool for 30 minutes.
For icing: In a medium bowl, stir together confectioners sugar, milk, and vanilla until smooth; drizzle over rolls.