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Preheat the oven to 350 degrees F (175 degrees C).
Heat a large skillet over medium-high heat. Cook and stir sausage with fennel, sage, salt, and pepper in the hot skillet until browned and crumbly, 5 to 7 minutes.
Place peppers into a baking dish. Spread 1/2 to 1 ounce cream cheese into each pepper. Add sausage mixture to each pepper and sprinkle with pepper Jack cheese.
Bake in the preheated oven until softened and bubbly, about 20 minutes.
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