Review work coverage & HSA rules
Find out whether you expect to retire at 65 or keep working. Check employer coverage, prescription coverage, and HSA implications early.
New to Medicare at 65? Focus on your enrollment dates, choosing Parts A and B, and how Advantage, Supplements, and Part D fit together. Learn at your own pace or talk to a licensed agent.
Prefer to talk? Call 833-265-9655
7-Month Enrollment Window
For most people, the IEP begins 3 months before the month they turn 65.
Part A & Part B First
Know whether you need to enroll, delay, or coordinate with employer coverage.
Then Compare Coverage
Advantage, Supplement, Part D, doctors, prescriptions, pharmacy, and costs.
Licensed Agent Help
No call-center pressure. No obligation to enroll after a review.
New to Medicare? Start Here
Before you worry about dates or plan names, it helps to know what each letter actually covers. Original Medicare is Parts A and B — everything else builds on top of that.
Covers inpatient hospital stays, skilled nursing care, hospice, and some home health. Most people get it premium-free after working and paying Medicare taxes for at least 10 years.
Covers doctor visits, outpatient care, preventive services, and durable medical equipment. Comes with a monthly premium that's set by Medicare each year.
An all-in-one private alternative to Original Medicare. Often bundles prescription drug coverage and extra benefits, usually within a provider network.
Covers prescription drugs. Sold by private insurers, either as a stand-alone plan or bundled into a Medicare Advantage plan.
Private insurance that works alongside Original Medicare to help pay costs it leaves behind, like the Part B 20% coinsurance.
Start Here · Your Free Medicare Starting Plan
Find your enrollment dates and see exactly how you need to sign up. Answer a few quick questions — no personal information required.
Want your complete personalized Medicare timeline?
Build My Medicare Timeline →How Do I Sign Up for Medicare?
Answer a few questions to find your next step.
Month-by-Month Roadmap
The goal is not to do everything at once. Handle the decisions in the right order so your coverage can start when you expect it to.
Find out whether you expect to retire at 65 or keep working. Check employer coverage, prescription coverage, and HSA implications early.
If you are not automatically enrolled and you plan to start Medicare at 65, this is when many people can apply for Part A and Part B through Social Security.
Decide whether to compare Original Medicare with Medigap and Part D or Medicare Advantage. Check doctors, prescriptions, pharmacy, travel, and budget.
Finalize the private coverage you want to begin with Medicare, verify start dates, and keep your Medicare number and Part A/Part B dates handy.
If you enrolled before your birthday month, Part B generally starts the month you turn 65. If you enroll during or after that month, coverage generally starts the next month.
Official timing references: Medicare.gov — when coverage starts and Social Security — signing up for Medicare.
Five steps, a lot of dates — totally normal to want a second set of eyes on this.
I Need Help With This →Still Working?
Do not automatically enroll in Part B — and do not automatically delay it. Active employer coverage, employer size, who pays first, drug coverage, and HSA contributions can all change the answer.
Review My Work Coverage
If coverage is based on your or your spouse's current employment, you may qualify for a Part B Special Enrollment Period later. Employer size can affect whether Medicare or the employer plan pays first.
20 or more employees: the group plan is generally primary, so you can usually delay Part B without a late penalty as long as that coverage continues. Fewer than 20 employees: Medicare is generally primary, so most people still need to enroll in Part B at 65.
Ask your benefits administrator how the plan coordinates with Medicare before you decide.
COBRA and retiree coverage are not treated the same as health coverage based on current employment for Part B enrollment timing.
If employment has ended, check your Part B deadline promptly instead of assuming COBRA or retiree coverage protects you from a late-enrollment problem.
Official references: Medicare.gov — working past 65 and Medicare.gov — COBRA coverage.
After Part A & Part B Timing
This is where the plan decision belongs — after you know your enrollment timing and how any employer coverage fits.
Path 1
You keep Original Medicare for hospital and medical coverage, add a Medigap policy to help with certain out-of-pocket costs, and usually add a separate Part D plan for prescriptions.
Path 2
You receive your Medicare benefits through a private Medicare Advantage plan. Plans can vary by ZIP code and may include prescription drug coverage and additional benefits.
We can compare the choices around your doctors, prescriptions, pharmacy, travel, budget, and coverage preferences.
Avoid Common Problems
Most turning-65 problems are timing or coordination problems — not complicated insurance math.
Part B Special Enrollment rules are tied to health coverage based on current employment. COBRA and retiree coverage require different timing decisions.
If you delay Medicare past 65, premium-free Part A can be retroactive up to 6 months. HSA contributions during a retroactive Medicare period can create tax problems.
A plan can look good on premium or extra benefits and still be a poor fit if your doctors, drugs, pharmacy, or travel needs were never checked.
Personal Medicare Review
The calculator gives you the dates. A licensed Lehigh Partners Senior Benefits agent can then help you apply those dates to your employer coverage, Medicare Advantage, Medicare Supplement, Part D, doctors, prescriptions, pharmacy, travel, and budget.
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Common Questions
A licensed Lehigh Partners Senior Benefits agent can help you understand enrollment timing, compare plan paths, and review options based on your doctors, prescriptions, pharmacy, ZIP code, budget, and coverage preferences.
No pressure. No obligation. Just clear Medicare guidance.