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Deadlines for changing your Medigap plan
In general, once you purchase your Medigap policy, preferably within the six-month open enrollment period, there is no deadline for switching to another policy. Your policy is guaranteed renewable every year.
However, if you decide to switch to another policy with the same company, contact the company and follow its procedures. If you want to switch to another policy with another company, contact the new company and go through its enrollment process letting it know that you currently have another policy and promise to cancel it. Do not cancel your old policy until you have had the new policy for the 30-day “free look period.” You will have to pay both premiums for one month, but it could be worth it if you change your mind and want to go back to your previous policy.
In either case, if you are past your six-month initial open enrollment period, you will be subject to medical underwriting, which means that the company could refuse to insure you based on health issues.