Preheat the oven to 350°F. Grease a casserole baking dish and set aside. Grab a separate large baking sheet. Add the cubed bread to the baking sheet. Drizzle with olive oil and toss together until evenly coated. Spread the pieces out so they don’t touch and pop in the oven to bake for 10-15 minutes, until crispy. Toss bread halfway through if needed. Set aside.
Grab a large skillet and heat over medium heat. Add the Italian sausage to the skillet and cook until browned. Transfer browned sausage to a dish and set aside. Add diced onion, diced celery and garlic to the same skillet and saute for 5 minutes. Add the apples and stir to combine. Cook for 5 more minutes, stirring every so often. Once the apples are slightly softened, remove the skillet from heat.
In a separate mixing bowl, add the toasted bread cubes, browned sausage, sauteed apples and veggies, dried cranberries, pecans, thyme, sage, cinnamon and nutmeg. Evenly pour the melted butter on top of everything then add the broth. Stir everything together gently until evenly moist, not soggy. Add salt and pepper then fold together. Let sit for 5 minutes.
Pour the mixture into the prepared casserole dish. Wrap the top of the dish in foil, then bake in the 350°F preheated oven for 30 minutes. Take the dish out of the oven and remove the foil. Bake for 15 more minutes or until gold and crisp on top. Remove and let cool for 5 minutes. Serve warm and enjoy!