I will be turning 65 on 6/28/2021. What is the latest date that I can sign up for SS without paying a penalty ...for anything, including prescriptions, etc all? This will be my initial sign up. Thanks Larry

Hi. I assume that you are referring to Medicare premium penalties, since you don't have to pay to file for Social Security benefits regardless of when you apply. If you have enough credits for Social Security benefits, Part A of Medicare is premium free regardless of when you apply. Part A coverage can be established retroactively for up to 6 months from your month of filing, so you potentially could apply for Part A coverage as late as December 31 2021 and still have your Part A coverage start June 1 2021.

However, you can't apply for retroactive Part B Medicare coverage. Since you'll reach age 65 in June 2021, if you want your coverage to begin June 1 2021 you'll need to apply sometime between March 1 2021 to May 31 2021. Your initial enrollment period (IEP) will continue through September, though, so you could sign up as late as September 30 2021 without be required to pay a premium penalty. But, if you sign up for Part B in September, your Part B coverage won't start until December 1 2021.

Even if you're past your IEP, though, you may be able to enroll in Part B of Medicare without paying a premium penalty as if you have primary health insurance coverage through your or your spouse's current employment. So, I can't give you a definitive answer without many more details about your circumstances. Furthermore, prescription drugs are not covered by Parts A or B of Medicare. You can get prescription drug coverage by signing up for Parts C or D of Medicare, but those are private insurance plans (https://www.medicare.gov/Pubs/pdf/11219-understanding-medicare-part-c-d.pdf).

Best, Jerry