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Preheat oven to 275°F. Spread bread on a large baking sheet and bake until dry to the touch, about 30 minutes. Let cool. Transfer to a large bowl.
Increase oven temperature to 350°F. Coat a 9-by-13-inch baking dish with cooking spray.
Heat oil in a large skillet over medium-high heat. Add leeks, fennel and squash; cook, stirring occasionally, until just starting to brown, 3 to 5 minutes. Reduce heat to medium and cook, stirring occasionally, until tender, 3 to 5 minutes more. Add garlic and cook, stirring, for 30 seconds. Add parsley and thyme and cook, stirring, for 30 seconds. Scrape the mixture on top of the bread. Melt butter in the pan, scraping up any browned bits, then scrape onto the bread. Add broth to taste, oysters and pepper to the bread mixture and stir to combine. Transfer to the prepared baking dish. Spray one side of a piece of foil with cooking spray and cover the stuffing, sprayed-side down.
Bake for 30 minutes. Uncover and continue baking until golden brown, about 20 minutes more.