Preheat oven to 350 degrees F.
Arrange challah bread cubes on a single layer on 2 large baking sheets. Bake for approximately 15 minutes until golden brown and dry. Place is a large mixing bowl and set aside.
Remove any crumbs from one sheet pan. Spread raw pumpkin seeds in a single layer and toast in the over for approximately 10 minutes. Add to bowl with dried challah bread cubes.
Drizzle extra virgin olive oil in a large skillet over medium high heat. Add turkey Italian sausage and cook until browned. Add to the bread mixture.
In the same skillet, add 2 tbsp of unsalted butter. Sauté sliced mushrooms until golden brown. Season with salt and pepper to taste. Add to the bread mixture.
Reduce heat to medium. Add another 2 tbsp of butter to the pan and sauté onions and celery until soft and translucent. Add garlic, rosemary, thyme and sage and sauté for 2-3 minutes more. Season with salt and pepper to taste.
To the pan add the white wine and scrape up the bits from the bottom of the pan. Let simmer on medium heat until the white wine reduces by half. Pour over the bread mixture.
To the bowl, add chicken stock. Start with 1 1/2 cups and add more in 1/2 cup increments as needed. Gently mix with a wooden spoon until bread crumbs are hydrated but not soft and soggy.
Crack 2 eggs into the bowl. Mix in until well combined.
Grease the bottom and sides of a 4 quart baking dish. Evenly spread your dressing into the dish and cover with foil.
Bake for approximately 30 minutes.
Remove foil and bake for 5-10 more minutes. Serve warm.