Healthcare In Retirement Issues – Will Healthcare Change As I Transition Into Retirement?
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2026 · WILL HEALTHCARE CHANGE AS I TRANSITION INTO RETIREMENT?
Do you expect to work
after turning age 65?
You may want to delay
enrollment in Medicare if
you want to continue to
contribute to your HSA.
Consider enrolling in
Medicare Part A & B when
you turn 65 if it makes sense
for your situation. For the
time being, it may be best to
stay with your current
coverage (e.g., Marketplace,
spouse's plan, etc.).
It may be advantageous
to move over to your
spouse’s plan.
You may be eligible for 18
months of coverage under
COBRA.
You may be eligible for 29
months of coverage under
COBRA.
The Health Insurance
Marketplace can offer
coverage until you are
eligible for Medicare.
Did you leave your employer
(voluntarily or involuntarily)?
Do you receive your health
insurance through your
employer?
Will you receive health
insurance from your
employer after you retire?
Can you be covered under
your spouse’s plan?
Check with your employer
to see how coverage works
with Medicare.
Consider enrolling in
Medicare Part A when you
turn age 65.
Consider enrolling in
Medicare Part A & B when
you turn age 65.
You can delay Part B until
you lose your
employer-sponsored
healthcare.
You will not pay a penalty
for delaying as long as you
enroll within 8 months of
losing your health plan.
Do you have an HSA and a
high deductible health plan?
See “Can I Make A
Deductible Contribution To
My HSA?” flowchart.
Did you meet the Social
Security definition for
disability?
Yes
No
Yes
No
No
Yes
No
Yes
You may be eligible for 36
months of coverage under
COBRA.
Was your spouse covered
and did they pass away?
Yes
No
No
Yes
No
Yes
No
Yes
No
Yes
Does your employer offer
health insurance and have
20 or more employees?
COBRA is expensive. You
may have to pay the full
insurance premium plus a
2% fee.
You may be eligible for a tax
credit, but it will go away
when you become eligible
for Medicare.
No
Yes
Do you work for a company
with 20 or more employees?
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Aaron Vaughn
30400 Detroit Road Suite 305a Westlake, OH 44145
aaron@defiantservicesllc.com
| 440-385-0208 |
www.defiantservicesllc.com
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