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Heat oven to 475°F.
Place dough on a work surface; lightly oil the surface with about 2 teaspoons of oil. Stretch or roll out to approximately 10" round. Cover with plastic and reserve.
In a large cast-iron skillet over medium-low heat, add about 1 tablespoon of the oil. Add the sausage, breaking it up into small pieces with a wooden spoon. Add the onion and fennel, and cook until the sausage is just cooked through and the onion and fennel are softened and fragrant; about 10 minutes. Stir in the garlic and cook until fragrant; about 1 minute. Transfer the sausage mixture to a bowl.
Remove the skillet from heat. Stretch the dough so that it is slightly larger than the diameter of the bottom of the skillet. Carefully lay the dough on the bottom of the skillet - use tongs or a spoon to help extend dough up the edges of the skillet by about ½-inch. Spread the sausage mixture over entire surface of dough. Top with the goat cheese. Drizzle with olive oil. Peek underneath the crust—the bottom should be golden brown and crisp from residual heat in the skillet. If it’s not, set over medium-low and cook until crust is golden brown, about 3 minutes.
Sprinkle with Craisins® Dried Cranberries and transfer the skillet to the oven. Bake until the crust is golden brown around the edges and the cheese is browned in spots and bubbling; about 10–14 minutes. Let cool 5 minutes, then top with red pepper flakes and basil. Drizzle with a bit more olive oil and serve.
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