General Discussion

Signing up up after 65, during the special enrollment period that begins when your work insurance ends is kind of a nightmare - especially if the initial enrollment period and the special enrollment period overlap. The rules are complex, and no one I was able to reach at Medicare could give me accurate advice until AFTER they rejected my special enrollment application because my initial enrollment period had not expired. That person at least was able to (accurately) tell me that when the enrollment periods overlap, the rules of the initial enrollment period governs.

(And whenever you enroll - making the once in a lifetime choice of which supplement plan to choose is straightforward, but a gamble, so it takes time to pick which insurance company is likely to cost you least over the rest of your life.)

I spent about 200 hours sorting out these two points.