Pat shrimp dry. In a bowl combine shrimp, 2 tbs jerk seasoning, 1 tbs olive oil, 1 tbs lime juice, 1 tsp minced garlic, 1 tsp salt and 1 tsp black pepper. Toss to coat and let sit 10–15 minutes at room temperature (or refrigerate up to 1 hour).

Cook shrimp

Heat a large skillet over medium-high heat. Add a drizzle of oil if skillet is dry. Add shrimp in a single layer and cook 1–2 minutes per side until opaque and lightly charred. Remove from pan and set aside.

For the pineapple chutney

In a medium bowl combine 1 cup diced pineapple, 1/4 cup diced red bell pepper, 1/4 cup diced red onion, 2 tbs chopped cilantro, 1 tbs lime juice, 1 tsp brown sugar, 1/4 tsp red pepper flakes and 1/4 tsp salt. Stir to combine and let sit 10 minutes to meld flavors. Taste and adjust salt, lime, or sugar as desired.

For the lime crema

Whisk together 1/2 cup sour cream, 1 tsp lime zest, 1 tbs lime juice, 1 tsp honey and 1/4 tsp salt until smooth. Refrigerate until ready to use.

For the chipotle sour cream

Stir together 1/2 cup sour cream, 1 tsp minced chipotle in adobo, 1 tsp lime juice and 1/8 tsp salt. Taste and add more chipotle for heat if desired. Refrigerate until assembly.

For assembling and cooking quesadillas

Preheat a large nonstick skillet over medium heat. Lay out 1 flour tortilla and sprinkle about 1/2 cup shredded Monterey Jack over half of the tortilla, leaving a small border.

Top the cheese with a quarter of the cooked jerk shrimp (roughly 4 oz), then spoon 2–3 tbs pineapple chutney over the shrimp, and scatter a few cilantro leaves if using. Add a small drizzle (about 1 tsp) of lime crema or chipotle sour cream if you like extra sauce inside.

Fold the tortilla over to make a half-moon and brush the skillet or the outside of the tortilla lightly with butter or oil. Place the folded quesadilla in the hot skillet. Cook 2–3 minutes per side, pressing gently, until golden brown and cheese is melted. Repeat with remaining tortillas and fillings.

Transfer cooked quesadillas to a cutting board and let rest 1 minute, then cut each into 3 wedges. Serve topped or drizzled with additional lime crema and chipotle sour cream, with lime wedges on the side.