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Place toothpicks in a small bowl and cover with water; let them soak to keep them from burning while cooking.
Mix 2 teaspoons chili powder and 2 teaspoons cumin in a shallow dish.
Preheat an air fryer to 400 degrees F (200 degrees C).
Place chicken breast on a flat work surface. Slice horizontally through the middle. Pound each half using a kitchen mallet or rolling pin until about ¼-inch thick.
Sprinkle each breast half equally with remaining chili powder, remaining cumin, chipotle flakes, oregano, salt, and pepper. Place ½ the bell pepper, onion, and jalapeño in the center of 1 breast half. Roll chicken from the tapered end upward and use 2 toothpicks to secure. Repeat with other breast, spices, and vegetables and secure with remaining toothpicks. Roll each roll-up in chili-cumin mixture in the shallow dish while drizzling with olive oil until evenly covered.
Place roll-ups in the air fryer basket with the toothpick side facing up. Set timer for 6 minutes.
Turn roll-ups over. Continue cooking in the air fryer until juices run clear and an instant-read thermometer inserted into the center reads at least 165 degrees F (74 degrees C), about 5 minutes more.
Drizzle lime juice evenly on roll-ups before serving.