Preheat oven to 450 degrees.
Toss pineapple chunks with oil and cayenne powder. Place on a baking sheet and roast for 15-20 minutes turning once, until caramelized. Remove from oven and cool.
In blender combine pineapple, cinnamon, nutmeg, milk, and ice cream. Blend until smooth.
Pour into a glass and garnish with coconut flakes. Enjoy!