@Opus 17 @Opus 17 - in the example, if you retire 12/31/25, I agree that HSA contributions would have had to stop back in June (6 months prior), but presuming you had private medical insurance through 12/31/25, Medicare would begin charging premium effective 1/1/26. There is no retroactive billing of premium (I went through this exact scenario myself), but as I recall you must apply for Medicare in a three month window post the date you lose private medical insurance to avoid any penalties for late enrollment.
