In a mixing bowl, whisk together warm coconut milk, active dry yeast, and granulated sugar until well combined. Let it sit for about 5 minutes until foamy. Next, gradually mix in all-purpose flour and softened unsalted butter until a soft dough forms. Knead the dough for about 5 minutes on a floured surface until smooth, then place it in a greased bowl and cover it with a damp cloth to let rise for 1 hour or until doubled in size.

While the dough rises, prepare the filling by draining the crushed pineapple using a fine strainer, ensuring you gently squeeze out excess moisture. Once the dough has risen, roll it out on a floured surface into a rectangle about half an inch thick. Spread softened butter evenly over the surface, then sprinkle the drained pineapple, brown sugar, shredded coconut, and cinnamon generously across the buttered area.

Carefully roll the dough tightly from one end to the other, forming a log shape. Once rolled, use a sharp serrated knife or dental floss to cut the log into eight even sections. Arrange the rolls cut-side up in a parchment-lined baking pan, ensuring they have space to rise. Cover them with a damp towel and let them rise for another 20 minutes.

Preheat your oven to 350°F (175°C) while the rolls complete their rise. Once preheated, bake the Piña Colada Cinnamon Rolls in the oven for about 25 minutes, or until they are golden brown and puffed up. Meanwhile, prepare the creamy glaze by mixing softened cream cheese, powdered sugar, and coconut milk until smooth. As soon as the rolls are out of the oven, drizzle the glaze over the warm rolls and sprinkle with additional coconut flakes and caramelized pineapple if desired.