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Heat the oil in a large nonstick skillet over medium heat. Add the onion and cook, stirring occasionally, until soft and translucent, 8 minutes. Add the garlic and cook for 1 minute more.
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Add the sweet potato, jalapeño, cumin, smoked paprika, and oregano, and season with salt and pepper. Toss to combine. Cover and cook until the sweet potato is crisp-tender, 5 to 8 minutes. (If your skillet doesn't have a lid just tent it with foil.) Stir in the corn and toss until heated through.
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Spread about 1/2 cup of the filling on one half of each tortilla and fold to enclose. Wipe out the skillet, then coat with nonstick spray and heat over medium-high heat. Working in batches, cook the quesadillas until crisp and golden brown, about 3 minutes per side.