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Step 1
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.
Step 2
Reduce the oven heat to 350°F and lightly grease or spray a 7.5x10-inch (or similar) pan with olive oil.
Step 3
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.
Step 4
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.
Step 5
Bake for 20 to 25 minutes or until the bread is golden brown on top. Sprinkle on the cranberries and chopped parsley, and serve.