Back “in the day” (that would be February of 2020), I advised clients to start their Medicare enrollment 2 to 3 months prior to the effective date they desired. If you were just turning 65, the online process was usually smooth and timely (3-week turnaround for your Medicare number). If you were 65+ and retiring, my advice was to head to a Social Security office at 8:20am with your L564 in hand and you’d be all set by 9:30am.
All of this changed on March 17, 2020.
That was the date that Social Security closed its offices due to COVID-19. Unfortunately, they appear to keep sinking deeper into a backlog of enrollment requests. During your first call to Social Security, you may be told that all they can do is schedule you for a telephone appointment 6 weeks in the future. During that call, they end with the disclaimer that it will take 30-60 more days to process your application.