Activate the yeast: Add the warm milk and yeast to the bowl of a stand mixer. Whisk gently to combine and let stand for about 5 minutes, until the yeast begins to foam.

Mix the dough: Add the softened butter, granulated sugar, and eggs to the yeast mixture and mix until combined. Add the salt and 4 cups of flour, mixing on low speed until a shaggy dough forms. Let the dough rest for 5 minutes.

Knead the dough: Fit the mixer with the dough hook and knead on medium-low speed for 5–7 minutes, until the dough is smooth and elastic. The dough should remain slightly tacky but should pull away from most of the sides of the bowl. If needed, add additional flour 1 tablespoon at a time, being careful not to over-flour the dough.

Let the dough rise: Transfer the dough to a lightly greased bowl, cover, and let rise in a warm place for about 45 minutes, or until nearly doubled in size.

Prepare the fruit: Drain the pineapple rings and maraschino cherries thoroughly and pat dry with paper towels. Finely chop enough additional pineapple to measure ½ cup, then pat it dry as well to remove excess moisture.

Make the filling: In a medium bowl, mix the softened butter, brown sugar, cinnamon, vanilla extract, and cherry emulsion until smooth and spreadable. Keep the chopped pineapple separate.

Roll out the dough: Turn the risen dough onto a lightly floured surface and roll into a large rectangle about ½ inch thick.

Fill the rolls: Spread the cinnamon filling evenly over the dough, leaving a small border around the edges. Sprinkle the drained chopped pineapple evenly over the filling.

Shape and cut: Starting from one long side, roll the dough tightly into a log. Pinch the seam to seal, then cut into 8 large rolls using a sharp knife or unflavored dental floss.

Prepare the pineapple topping: Lightly grease the sides of a deep round pie dish or baking dish. Stir together the melted butter, brown sugar, and pineapple juice, then spread the mixture evenly across the bottom of the dish.

Arrange the fruit: Place the pineapple rings over the brown sugar mixture in a decorative pattern. Add one maraschino cherry to the center of each pineapple ring, adding extra cherry halves between the rings if desired.

Arrange the cinnamon rolls: Place the cut cinnamon rolls directly over the pineapple layer, arranging them snugly in the dish with one roll in the center and the remaining rolls around it.

Second rise: Cover the dish loosely and let the rolls rise for about 30 minutes, or until noticeably puffy. Meanwhile, preheat the oven to 350°F.

Add the cream: Just before baking, warm the heavy cream slightly and pour it evenly over and around the cinnamon rolls.

Bake: Bake for 28–35 minutes, or until the rolls are golden brown and the center rolls are fully baked. If the tops begin browning too quickly, loosely cover the dish with aluminum foil during the final 10 minutes.

Rest before flipping: Remove the rolls from the oven and let them rest in the pan for 5–7 minutes. Avoid cooling them much longer, as the brown sugar topping will begin to set and may stick to the pan.

Invert the rolls: Place a large serving platter over the baking dish. Holding the platter and dish securely together, carefully flip them in one motion. Slowly lift away the baking dish, repositioning any pineapple rings or cherries that may have shifted.

Make the cream cheese drizzle: Beat the softened cream cheese and butter until smooth. Add the powdered sugar and vanilla and mix until combined. Add heavy cream 1 tablespoon at a time until the frosting is thick but pourable.

Finish and serve: Drizzle the cream cheese frosting lightly over the warm cinnamon rolls, leaving the caramelized pineapple rings and maraschino cherries visible. Serve warm.