Preheat the oven to 400 degrees F. Lightly grease a 9x13 inch baking dish with softened butter.

Halve both acorn squash, remove the seeds *but save them for roasting! Next cut the squash into wedges. Line the squash wedges up on the prepared pan. Evenly sprinkle the brown sugar over the the squash and then season with salt + pepper. Now spoon the crushed pineapple over the squash wedges, allowing some of the pineapple to fill the cavity of the squash wedges while the remaining pineapple gathers around the squash.

Place the butter in a small saucepan set over medium heat until just browned. Butter will melt, foam and froth, then begin to brown along the bottom. Remove from the heat and whisk the browned bits of butter off the bottom of the pan. Whisk in the cinnamon, chili powder + pepper. Pour the butter over the squash, using your hands to rub all over the squash. Cover the dish with foil and place in the oven. Roast for 30 minutes and then remove the foil and roast for another 30 minutes or until the squash is tender and caramelized.

Sprinkle the squash with pomegranate arils and toasted acorn squash seeds (recipe below). Serve warm.

To roast your reserved acorn squash seeds, rinse them off and pat them dry. Toss with 1 tablespoon olive, salt + pepper. Place in the oven at 400 degrees F and roast for 10 minutes or until golden brown and toasted.