Drizzle oil in a cast iron pan and rub the acorn flesh and all over the bottom. Add a tiny drizzle, or rub the oil down into the well of each squash and season well with salt and pepper if desired.
1 Acorn Squash, Olive Oil, Salt and Pepper
Roast for about 20-30 minutes, face side down and with foil over the backs until the flesh is browning and caramelizing.
Flip over and rub the rims with a pat of butter and then throw the pat into each well.
2 Tablespoons Butter
Sprinkle liberally with brown sugar in the well and rims as well as the seasoning divided between the two squash.
2-4 Tablespoons Dark Brown Sugar , 1/4 teaspoon Cinnamon, 1/4 teaspoon Cardamom
Roast, cut side up, covered with foil for another 20-25 minutes or until tender and mashable. Serve with a little more salt if needed.