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Preheat oven to 400°F (200°C).
Place pumpkin on a baking sheet and drizzle with olive oil. Add salt and pepper, then mix. Bake 35 to 40 minutes, or until pumpkin is tender. Stir halfway through baking. Remove cooked pumpkin from oven and mash lightly with a spoon. Set aside.
Place onion and 3 tbsp. olive oil in a large skillet on medium-low heat. Season with salt and pepper, and stir. Cook for about 12 minutes until onions are translucent and caramelized. Add oil as needed. Onions shouldn’t brown. If they do, turn down the heat.
Place chicken breasts on a baking sheet and drizzle with olive oil. Sprinkle with Herbes de Provence, to taste. Season with salt and pepper and massage to coat chicken.
Put chicken in oven and roast for 15 to 20 minutes or until the internal temperature reaches 165 °F (74 °C). Let cool 5 minutes, then dice. Set aside.
Place two tortillas on a work surface and spread half of cheese, chicken, pumpkin, and onions over each. Add remaining cheese on top, cover with two other tortillas, and press down to compact and spread ingredients to the edges.
Drizzle olive oil in a large skillet over medium-low heat and carefully place one quesadilla in the skillet. Cook for 2 to 3 minutes until the underside is a nice golden brown. Turn quesadilla over delicately and cook 2 to 3 more minutes until golden. Place in oven on low heat to keep warm while other quesadilla cooks.
Add all chipotle sour cream ingredients to a bowl and mix. Refrigerate until ready to serve.
Serve quesadillas with salsa and chipotle sour cream.
Place a large plate over the skillet and flip it to turn the quesadilla over without it falling apart.