Preheat the oven to 400°F and line a baking sheet with parchment paper. Place the butternut squash cubes on the pan and toss with a drizzle of olive oil and generous pinches of salt and freshly ground black pepper. Roast 25 minutes or until tender.
Reduce the oven heat to 350°F and lightly grease or spray a 7.5x10-inch (or similar) pan with olive oil.
In a large skillet, heat 1 tablespoon of olive oil over medium heat. Add the leeks, celery, and generous pinches of salt and pepper and cook until translucent, about 5 to 7 minutes. Add the garlic, chopped sage, and rosemary and stir. Add the wine, stir, and cook for 30 seconds.
Stir in the bread, then 1 cup of the broth, and gently toss until the bread cubes are evenly coated. Transfer to a baking dish and drizzle on the remaining ½ cup of broth, especially over areas that may seem dry. Evenly distribute the butternut squash, pearl onions, and sage leaves through the spaces between the bread. Drizzle 1 tablespoon of olive oil on top along with a few more pinches of salt and pepper.
Bake for 20 to 25 minutes or until the bread is golden brown on top. Sprinkle on the cranberries and chopped parsley, and serve.
Recipe by Love and Lemons at https://www.loveandlemons.com/butternut-squash-casserole/