Preheat your oven to 400°F (200°C). Toss the cubed squash with a tablespoon of olive oil, cinnamon, salt, and pepper, then spread evenly on a baking sheet. Roast for about 20-25 minutes, until tender and slightly caramelized.
While the squash roasts, prepare the cranberry layer by rinsing the cranberries and setting them aside. In a mixing bowl, combine the shredded cheese and breadcrumbs, mixing well to create a flavorful topping.
Once the squash is roasted and still warm, transfer it to a greased baking dish. Scatter the cranberries over the squash evenly, then sprinkle the cheese and breadcrumb mixture on top.
Place the casserole in the oven and bake for an additional 15-20 minutes, until the topping is golden brown and bubbling around the edges.
Remove the casserole from the oven and let it rest for a few minutes to settle. Serve warm, allowing the flavors to meld and the topping to stay crispy.