Top 1 tortilla with the peppers, arugula, and goat cheese; season with ¼ teaspoon each kosher salt and black pepper and top with the remaining tortilla.
Heat 1 teaspoon of the oil in a large skillet over medium heat. Add the quesadilla and cook until golden brown and crisp, 2 to 3 minutes per side, adding the remaining oil to cook the second side. Cut into 8 wedges.
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