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Drain and rinse the cherry peppers (if jarred).
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Cut off the tops and carefully remove the seeds with a small spoon or knife.
Make the Filling
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Cut the provolone into small cubes (around ½ inch).
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Cut the prosciutto slices into strips long enough to wrap around each cheese cube.
Stuff the Peppers
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Wrap each provolone cube with a strip of prosciutto.
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Stuff the wrapped cheese into each pepper until snug.
Marinate
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Arrange the stuffed peppers in a jar or container.
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In a small saucepan, warm olive oil, garlic, oregano, red pepper flakes, and vinegar over low heat for 2–3 minutes (don’t let the garlic brown).
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Pour the warm marinade over the peppers, ensuring they’re fully covered.
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Let cool, then refrigerate for at least 12 hours (best after 24 hours).
Serve
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Bring to room temperature before serving.
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Garnish with chopped parsley if desired.
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Enjoy as part of an antipasto platter with olives, salami, and crusty bread.