Why did you close the thread on the person who asked about buying US health insurance if you live in the DR? I think you pulled the plug pre-maturely. Why? To answer the person who originally asked the question, if you are living in the DR for even half the year and you still have a US residence than you would be obligated by law to have Health Insurance from a US provider. 330 days is basically the entire year in the DR. At which point you would have to apply for residency in the DR and most likely would not be maintaining a US address. To the person who asked how the IRS could collect a penalty for not having insurance they simply send you a letter stating the penalty and how much you owe and are obligated to send them a check. If you don't you would be considered a tax evader just as if you didn't file your return properly and needed to pay additional.