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Preheat the oven to 400°F (205°C). Arrange the pepper halves cut-side up in a 9x13-inch baking dish. Brush the inside of each half with a thin layer of olive oil (about 1/2 tbsp total) and season lightly with salt and pepper. Roast for 15 minutes, until the peppers are just beginning to soften but still hold their shape.
While the peppers roast, heat the remaining 1/2 tbsp olive oil in a large skillet over medium-high heat until shimmering. Add the sausage and cook, breaking it into small crumbles, for 5–6 minutes, until browned throughout with no pink remaining.
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