Preheat your oven to 400°F (200°C).
Cube the squash into even-sized pieces to ensure even roasting.
Toss the squash with olive oil, salt, and pepper, and spread in a single layer on a baking sheet.
Roast the squash for 25-30 minutes, or until tender and golden.
While the squash roasts, prepare the cranberry filling by placing cranberries in a mixing bowl.
Add cinnamon, salt, and a tablespoon of sugar (optional), and stir to combine.
In a separate bowl, combine breadcrumbs, shredded cheese, and a drizzle of olive oil.
Once the squash is roasted, transfer it to a large baking dish.
Sprinkle the cranberry mixture evenly over the roasted squash.
Top with the breadcrumb and cheese mixture, pressing it down slightly.
Bake for 10-15 minutes until the top is golden and crispy.
Serve hot and enjoy the comforting flavors of fall.