Before 65, most people have one health plan that covers the whole household. At 65, coverage becomes individual, it comes in parts, and the deadlines carry penalties. Knowing how the two systems differ helps you avoid gaps and late fees.
How health insurance works before 65
Most people under 65 are covered through an employer or buy a plan themselves. In Connecticut, individual plans are sold through Access Health CT, the state’s health insurance marketplace. Open enrollment for 2027 coverage runs from October 23, 2026 to January 15, 2027.
These plans work the same basic way. You pay a monthly premium, meet a deductible, and pay copays inside a provider network. One plan can cover a spouse and children, and it includes prescription coverage and a yearly out-of-pocket maximum.
What changes at 65
Medicare is individual. There is no family plan, so each spouse enrolls separately, and a younger spouse needs their own coverage until they turn 65.
It also comes in parts. Part A covers hospital care and Part B covers doctors and outpatient care. The standard Part B premium in 2026 is $202.90 a month. Prescriptions fall under Part D. Part C, Medicare Advantage, bundles these into a private plan.
The biggest surprise for most people is that Original Medicare has no out-of-pocket maximum. After a $283 deductible, you pay 20% of most Part B services with no ceiling. That’s why most people add either a Medicare Supplement policy or choose a Medicare Advantage plan, which does have a yearly limit.
Having both Medicare and employer coverage
If you’re still working at 65, the size of your employer decides which coverage pays first. At a company with 20 or more employees, the group health insurance pays first and Medicare is secondary. You can usually delay Part B without a penalty and sign up within eight months of leaving the job.
At a company with fewer than 20 employees, Medicare pays first, and you’ll generally want Part B at 65.
COBRA doesn’t extend your time to sign up. If you have a Health Savings Account, plan to stop contributing about six months before you apply for Medicare.
The mistakes that cost money
The first is assuming Medicare starts automatically. It does only if you’re already receiving Social Security at least four months before you turn 65. Everyone else has to sign up during the seven-month Initial Enrollment Period around their 65th birthday. If you delayed because of employer coverage, a Special Enrollment Period applies instead.
The second is missing that window without other qualifying coverage. The Part B late penalty is 10% for each full 12 months you were eligible and didn’t enroll, and it generally lasts for as long as you have Part B.
The third is assuming Medicare covers everything. It doesn’t cover most dental, vision or hearing care, or long-term custodial care.
Questions about your own situation
If you’re nearing 65 or working past it, The Jones Group can look at your current health insurance and show you how Medicare would fit with it. Call us in Wethersfield at (860) 529-3788.
