Preheat oven to 425° F (220° C). Arrange squash halves cut-side up on a baking sheet.
In a bowl, mix 6 tablespoons melted butter, crushed pineapple, dark brown sugar, cinnamon, chipotle powder, and a pinch of flaky sea salt. Rub squash all over with half of this sauce.
Flip squash cut-side down and bake for 20 minutes.
Remove squash from oven. Flip cut-side up, brush with remaining sauce. Bake for another 10 minutes, until caramelized and tender.
Meanwhile, in a skillet, melt the remaining 2 tablespoons of butter over medium heat. Add sage leaves and cook until butter browns and sage crisps.
Serve squash warm, topped with the crispy sage and a final sprinkle of flaky sea salt.
Notes
Nutrition information is an estimate, calculated automatically. Values vary with brands, substitutions and portion sizes.