Preheat the oven to 400°F.
In a food processor or blender, add the canola oil, salt, pepper, onion, bell pepper, jalapeño, tomatillos, rosemary, sage, garlic, and red pepper flakes and blend until smooth.
Coat both sides of the chicken breasts with half of the mixture.
Place a chicken breast on top of 1–2 slices of prosciutto, and starting at one end, tightly roll the prosciutto and chicken together to form a roll. Secure with a toothpick.
Repeat for remaining chicken breasts.
Add more of the spicy oil mixture to each roll of chicken and prosciutto, saving the second half of the sauce in a separate container for use before serving.
Remove toothpicks and place rolls seam-side down onto a foil-lined baking sheet.
Bake for 30–40 minutes.
Remove from heat and allow to sit for 5–10 minutes.
Slice the rolls and drizzle the remaining oil mixture over the finished product.
Serve immediately.