In the bowl of a stand mixer fitted with the paddle attachment, combine warm milk, granulated sugar, and yeast. Let stand until foamy, about 10 minutes. Add 1 cup flour, beating at low speed to combine. Add melted butter and ½ cup flour, beating until combined. Add eggs, beating to combine. Gradually add salt and remaining 1½ cups flour, beating until a soft dough forms.
Spray a large bowl with cooking spray. Place dough in bowl, turning to coat top. Cover and let rise in a warm, draft-free place (75°) until doubled in size, about 1 hour.
Spray a 10-inch cast-iron skillet with cooking spray. On a lightly floured surface, roll dough into an 18x16-inch rectangle. Spread with preserves, leaving a ½-inch border. Sprinkle generously with strawberries. Starting at one long side, roll up dough, jelly roll style, pressing seam to seal. Place seam side down on a cutting board, and cut in half lengthwise, pinching top to seal. Carefully twist dough pieces around each other, and place in prepared pan, cut side up, tucking ends underneath. Cover and let rise in a warm, draft-free place (75°) until doubled in size, about 45 minutes.
Preheat oven to 350°. Bake until a wooden pick inserted in center comes out clean, 35 to 40 minutes (loosely cover with foil to prevent excess browning, if necessary). Let cool completely.
In a small bowl, whisk together confectioners’ sugar and cream until smooth. Drizzle over cooled bread.