(A) Should I chose "yes" when asked If I had Medicare for any part of 2023? YES (even if only for Part A)
(B) Should I chose "Yes" when asked if I was over 65 when distribution was received? Are you saying that some of your distributions were NOT for qualified medical expenses? If yes, then answer yes ONLY if you were actually over 65 in the month the distributions were made. Whether or not you had Medicare is irrelevant.
(C) which boxes do I check for each month after May? Check Medicare for any month for which you were on Medicare on the first day of the month.
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