Retiring After 65
Pending review by Liz McPherson, licensed insurance agent since 2007 · Updated September 25, 2026
If you're signing up for Medicare after 65, many people stop HSA contributions about 6 months before they apply, because Part A coverage can be backdated up to 6 months. Once you're enrolled in any part of Medicare, you can't contribute to an HSA.
Here's the catch: when you enroll in Medicare after 65, Part A usually starts up to 6 months before the month you apply (but never before the month you turned 65). Contributions made during those backdated months can cause a tax headache. The good news is that you can keep using the money already in your for qualified medical expenses, including some Medicare premiums. Taking Social Security benefits also enrolls you in Part A automatically, so that timing matters too.[LIZ REVIEW]
When you plan to apply, whether you're taking Social Security, and your employer's contribution schedule. Check with your tax advisor for your specific numbers.
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