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Baggage on a Cape Air connection works differently coming vs going.
San Juan to Tortola: Your do not do anything with your checked baggage. It will be transferred directly to your Cape Air flight. No need to go through security - you will remain inside the secure zone for the entire time.
Tortola to San Juan: You must pick up your baggage at customs baggage claim and walk it through US customs and Immigration, then take it to Delta to check it in. You will be outside the secure zone, and will have to go through TSA security to get to your departure gate.
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