Craig

Brian.. so if I read that right. - I can stay on the COBRA for no more than 8 months. Because I HAVE to enroll in Medicare by May, 2026 to avoid penalty from late sign up. (Termination date is August 4, 2025). - i would be HSA compliant as long as I didn’t register for any Medicare. - I need to check the HDHP plan and see if it will pay as primary if I’m not enrolled in Medicare or if it automatically considers the HDHP as secondary payer since I’m 65+ and Medicare eligible. You would think Medicare would be happy to have me not enroll as long as possible as it would save them money potentially!! Go figure. i really hate to lose the HSA contributions! Its been really good for us.

Thank you for your reply. My termination package specifically specifies a 6 months + 12 months for a total of 18 months. I have found that if I’m on COBRA payments I’m still considered to be on a HDHP and can still contribute to the HSA. I cannot find any info if that changes if I’m Medicare eligible but don’t sign up. I haven’t found if Medicare penalizes me for remaining on an existing employer HDHP via COBRA and not signing up for Medicare upon termination. The IRS doesn’t have a problem with it it appears for purposes of the HSA contributions. Yes,.. the COBRA payments for the extra 12 months maybe more $$$. (First six months paid by company). But if the additional contribution amounts remain in the tax free HSA for 10-20 yrs it maybe worth it.

I think I know the answer but I’m not 100% sure. I recently had my job moved to Mexico. My severance date is in August when I’ll be 66, 8 months old. (Born in 12/1958). My wife is 72 and collecting Medicare. She is not on my HDHP nor the HSA. My name only as an individual. I am fully planning to continue working till I’m 70. I am probably not going to file for SS so we can maximize our payments. I have an HSA I’ve been contributing the max to for a number of years. My HDHP is via my employer. So I was planning to contribute the max to my HSA until Dec, 2028. We planned to use it for long term healthcare if we ever needed it. So we really wanted to max it out and we never draw down from it. But I know I can’t contribute now once my employment is over. BUT….. as part of my package, the company pays 6 months of COBRA of my HDHP. And then I can choose to pay COBRA for another 12 months if I want. I will be working as an independent consultant, most likely as a 1099. Would I still be considered qualified to contribute to my HSA during the company paid COBRA period? Even though I could sign up for Medicare? What about when I take over the COBRA payments? Can I still not sign up for Medicare and contribute to the HSA? if I wasn’t eligible for Medicare, I’m pretty sure I can contribute to the HSA while on COBRA. I’ve found some articles on that. But would the IRS consider me covered by an employer’s HDHP or disallow it since I could apply for Medicare? I know I’d pay a lot for the COBRA but adding another 10+K to my HSA that can grow tax free a few more decades may be worth it. Both my wife and I are healthy, we have no medical problems, are active, and have longevity with both our parents having lived well into their 90’s and one to 103. Thanks in advance for any insights. Craig