I purchased your book several years ago...and LOVE it - tagged many pages...and refer to it (and to others) often...it's become my SS bible. Sadly, though, I'm unable to find a definitive answer to what I consider a very simple question...so, I write to ask your help. I turn 70 in Feb 2021 and plan to begin drawing SS around that time. We maintain a family HSA (hi-D eligible) through my husband's employer. We make our own direct contributions and declare them on our yearly tax returns). Are there rules/deadlines we need to consider (don't want to pay a penalty) that might conflict with applying for and/or collecting SS.? Can my husband (employed and only 65) continue to contribute to our "family" HSA even after I apply for/begin collecting SS? Your guidance (and your commitment to SS info) is greatly appreciated!! :)liz

Hi Liz,

Your questions probably would be simple to answer for an expert on income tax regulations, but my only area of expertise is Social Security benefits. HSA rules are regulated by the IRS, not Social Security (https://www.irs.gov/forms-pubs/about-publication-969). Here is what I can tell you. If you apply for Social Security benefits you'll be required to file for Part A of Medicare at the same time, and you'll automatically be enrolled in Part A of Medicare effective with the 1st day of the 6th month prior to the month that your application is filed.

For example, say that you apply in December 2020 and claim your Social Security benefits effective with February 2021. You would then be automatically enrolled in Part A of Medicare effective June 1 2020. However, people who are over full retirement age (FRA) are allowed to claim their Social Security benefits up to 6 months prior to the month in which they file their application. Therefore, if you want to delay Part A of Medicare as long as possible but still be able to claim your Social Security effective with February 2021, you could file your application as late as August 2021. Your Part A coverage would then start on February 1st 2021.

My understanding is that you can't deduct HSA contributions starting with the first month of Medicare coverage, but I'm not an expert on IRS regulations. You may want to direct your questions to an employee of the IRS or a tax expert.

Best, Jerry