Step 1: In a large mixing bowl, combine the warm milk and yeast. Let it sit for 5 minutes until the yeast blooms and becomes frothy. Stir in the sugar, melted butter, egg, and salt. Gradually add the flour one cup at a time, stirring until a soft dough forms. Knead for about 8 minutes until the dough is elastic and smooth. Cover and let rise in a warm place for about 1 hour or until doubled in size.
Step 2: While the dough is rising, prepare the cheesecake filling. In a bowl, beat the softened cream cheese with powdered sugar and vanilla extract until smooth and fluffy. Set aside. If using fresh strawberries, place them in a small saucepan with lemon juice and sugar. Cook over medium heat until the strawberries break down and become syrupy, about 5–7 minutes. Let cool. If using preserves, skip this step.
Step 3: Once the dough has doubled, roll it out on a floured surface into a large rectangle, about ¼ inch thick. Spread the cream cheese filling evenly across the dough, leaving a small border along the edges. Spoon the strawberry mixture or preserves over the cream cheese and use a spatula to gently swirl it across the surface.
Step 4: Roll the dough tightly, starting from the long edge, to form a log. Pinch the seam to seal and cut into even slices—about 1 ½ inches thick. Arrange the rolls in a greased baking dish or on a parchment-lined sheet pan, leaving a little space between each. Cover loosely and let them rise again for about 30 minutes while the oven preheats to 350°F (175°C).
Step 5: Bake the rolls for 22–28 minutes or until golden brown and bubbling. While they’re baking, make the shortcake crumble by mixing crushed vanilla wafers, melted butter, and strawberry Jell-O powder in a bowl until it forms a crumbly texture. Remove rolls from the oven and let cool for 10 minutes before sprinkling the shortcake crumble generously over the top. Drizzle with optional vanilla glaze before serving.