Nice coverage of the HSA, Adam Parsons. When my wife and I first encountered this option, we were clueless about what it was. Later, when we saw its merits, we couldn’t consistently opt for it because employers changed a few times and the health care options changed with them.

But we have availed this option whenever we could, especially noting that employers are contributing as well. Good point about that being a bribe, but it still helps.

One thing that I discovered recently may need to be kept in mind by folks approaching retirement. Apparently, signing up for Medicare has a requirement that you shouldn’t have had HSA contributions made during the 6 months prior to enrollment!

If you are born in the first half of the year, this may affect what you should have done for the previous year, in the year prior, if I am interpreting this right.

Say you are turning 65 in Feb 2020. Medicare enrollment window is Nov 2019 through May 2020. Regardless of when you decide to enroll in this window, this would require you to not have had HSA contributions in late 2019. Noting that open enrollment period is generally in November for the following calendar year, this would imply that you shouldn’t have chosen the HDHP option for 2019 during open enrollment in Nov 2018, because you will go on Medicare in 2020!

Much of what I write is my playing through the scenario based on that one requirement I read. I welcome comments on any fallacy in my line of reasoning.

Again, thanks for a good write up.