In this week’s column, Phil Moeller, the author of Get What’s Yours for Medicare: Maximize Your Coverage, Minimize Your Costs and co-author of the updated edition of How to Get What’s Yours: The Revised Secrets to Maxing Out Your Social Security, addresses health savings accounts and how one man can maximize his benefits through smart timing.

Got a question of your own about Medicare or Social Security? Send it to

HSA vs. Medicare

Question: Phil, I’m hoping you can answer a tough question for me. Here are some needed background details: 

  • I will turn 70 next month and my wife, Sally, will turn 65 in October.
  • I work for a large company with more than 25,000 employees and have healthcare thru them for Sally and myself. I plan on working through the end of next year.
  • I have not claimed Social Security benefits yet and have been waiting until I turn 70. I have a health savings account (HSA) and contribute to it $500 a month, along with another $500 a quarter from my company, for a total of $8,000 in 2019.
  • I have not enrolled in Medicare Part A or Part B.

Please review the following plan and let me know if you think it is doable.

I would like to contribute as much money to my HSA as possible so I can benefit from these pre-tax contributions.

I know once I start taking Social Security I also have to enroll in Medicare Part A. I know there is a retroactive rule that says I can’t contribute to an HSA six months before I start Medicare.

If I start Social Security and Part A of Medicare next month, it seems that I already will have contributed too much to the HSA this year.

I know I can apply for Social Security as late as age 70 ½ and will quality for six months of retroactive benefits and thus not lost any money.

I am thinking that by doing this, I could continue contributing to my HSA thru August and then stop for year, as this would be six months before I started drawing Social Security and Part A of Medicare.

I have tried to educate myself on this stuff. I have read your Social Security book and have enrolled in the maximization software provider by your co-author, Larry Kotlikoff. I also am about halfway through your book, “Get What’s Yours For Medicare.”

I haven’t stumbled on the answer to this strategy, so I am hoping you can shed some light on it for me.

Thanks for all you have done for us common folks trying to navigate the entry into this era of our lives without getting tripped up.



Dear Gary:

You get five gold stars for reader of the year! Normally, the questions I receive are brief and my answers are not! Today, the roles are reversed.

Your thinking and maximization strategy fulfill my highest expectations for how I hoped our books would inform people to make better decisions about the Social Security and Medicare – the two programs most critical for successful aging by older Americans.

I especially like the tactic of waiting until 70 and a half to file for Social Security to extend your HSA contribution window. Very savvy.

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