Not that I didn't want to answer your questions but you're getting the cart before the horse a bit.. Take it step by step, you got a while to figure out what to do next year 𝗧𝗼 𝗴𝗲𝘁 𝘁𝗵𝗲 "𝗳𝗿𝗲𝗲 𝘀𝗲𝗰𝗼𝗻𝗱 𝘆𝗲𝗮𝗿" 𝗼𝗻 𝘁𝗵𝗲 𝗢-𝗔, 𝗮𝗹𝗹 𝗜 𝗻𝗲𝗲𝗱 𝘁𝗼 𝗱𝗼 𝗶𝘀 𝗲𝘅𝗶𝘁 𝗮𝗻𝗱 𝗲𝗻𝘁𝗲𝗿 𝗧𝗵𝗮𝗶𝗹𝗮𝗻𝗱 𝗼𝗻 𝗼𝗿 𝗷𝘂𝘀𝘁 𝗯𝗲𝗳𝗼𝗿𝗲 𝟯𝟭 𝗝𝘂𝗹 𝟮𝟬𝟮𝟳? As long as you get a new year mandatory health insurance (which you PRINT OUT) and exit/re-enter on/before your OA visa will expire you will get stamped in for a whole new year (or as long as your insurance is valid for up to a year) 𝗗𝗼 𝗜 𝗻𝗲𝗲𝗱 𝘁𝗼 𝗽𝗿𝗼𝗮𝗰𝘁𝗶𝘃𝗲𝗹𝘆 𝘀𝗵𝗼𝘄 𝘁𝗵𝗲 𝗼𝗳𝗳𝗶𝗰𝗲𝗿 𝘁𝗵𝗲 𝗻𝗲𝘄 𝗶𝗻𝘀𝘂𝗿𝗮𝗻𝗰𝗲 𝗳𝗼𝗿 𝗮𝗻𝗼𝘁𝗵𝗲𝗿 𝘆𝗲𝗮𝗿 (𝗱𝗶𝗴𝗶𝘁𝗮𝗹 𝗼𝗿 𝗽𝗮𝗽𝗲𝗿?), 𝗼𝗿 𝘄𝗶𝗹𝗹 𝗶𝘁 𝗯𝗲 𝗶𝗻 𝘁𝗵𝗲𝗶𝗿 𝘀𝘆𝘀𝘁𝗲𝗺 𝗮𝗹𝗿𝗲𝗮𝗱𝘆? Yes, PRINT the new year insurance coverage paper the carrier sends you when you renew, NO it will NOT be in their system 𝟴𝟬𝟬𝗸 𝗧𝗛𝗕 𝗶𝗻 𝗮 𝗧𝗵𝗮𝗶 𝗯𝗮𝗻𝗸 𝗮𝗰𝗰𝗼𝘂𝗻𝘁 𝗶𝘀 𝗻𝗼𝘁 𝗻𝗲𝗲𝗱𝗲𝗱 𝗿𝗶𝗴𝗵𝘁? Correct to get that "free" second year you don't show proof of funds.. You're only activating a new entry on a year-long, multi-entry visa and getting a new year entry stamp.