You Can’t Make This Up
This is a modified passage in the new edition of Maximize Your Medicare (I may have mentioned it is available for pre-order, you can click here.
Bottom line: look at the list, there is no way for the coverage date to begin on May 1. This is due to a very technical reason, and the manual overrides are riddled with errors at the SSA.
The point is to have your employer-sponsored coverage end the day prior to the month that you turn 65, OR continue to work until 4 months after the 1st of the month that you turn 65.
If you choose anything other than that, then you will face undue stress, because then you could either be double covered when you do not need, or you would have a lapse in coverage.
If you wait until the month of your sixty-fifth birthday, or later, then your Medicare Part B effective date will be delayed by up to three months. Importantly, this is subject to change in 2023, when this schedule of delays will no longer exist, due to provisions of the newly-enacted BENES Act. The coverage date will begin the month after applying. For 2022, however, this schedule will exist:
If John signs up in March, then the effective date is April 1.
If John signs up in April, then the effective date is June 1.
If John signs up in May, then the effective date is August 1.
If John signs up in June, then the effective date is September 1.