Your Medicare Initial Enrollment Period is a 7-month window centered on your 65th birthday. Most people should start the conversation 4 to 6 months before that. Here's what to do, when, and why — without the marketing pamphlets the carriers are about to bury you in.
Start the conversation. Talk to a licensed agent certified to sell Medicare plans. Decide whether to enroll in Medicare or stay on employer coverage. If your employer has fewer than 20 employees, you almost certainly want Doctor coverage (Part B) at 65.
Your IEP officially opens. If you're already collecting Social Security, Medicare's Hospital and Doctor parts (A and B) enrollment is automatic. If not, you sign up at SSA.gov or in person at the New Haven, New London, or other SSA office.
This is when most people pick a Supplement (Medigap) or Advantage plan, plus prescription drug coverage. Coverage typically starts the first day of your birthday month if you signed up early enough.
The IEP window closes. If you missed it without other coverage, late-enrollment penalties may apply — permanent, surcharged onto your Doctor-coverage premium for life. Don't miss it.
This is the structural choice. Once made, it's not impossible to switch, but switching from Advantage back to Original + Supplement gets harder over time because Supplement plans can use medical underwriting after your initial enrollment window closes. Connecticut has stronger protections than most states, but it's still worth getting this right the first time.
Original Medicare + Medigap (Supplement) + prescription drug plan: predictable, broad provider access, higher monthly premium. For shoreline retirees who travel south for the winter or visit family across state lines, this is often the better fit.
Medicare Advantage (Part C): one bundled plan from a private carrier, often $0 monthly premium, often includes dental and vision and prescription drug coverage, but uses a network and has higher cost-sharing on heavy use. For retirees who stay local and don't see many specialists, this can work very well.
If you went with Original + Supplement, you also need a stand-alone prescription drug plan (Part D). The cheapest plan for you depends on which prescriptions you take. I run your prescription list through Medicare.gov's official Plan Finder against each plan's formulary — it's the only tool that returns accurate total-annual-cost numbers.
The "pick the lowest premium" instinct gets people in trouble. The cheapest premium often has the most expensive drug copays. We optimize on total annual cost, not monthly premium.
If you're still working with employer health coverage at 65, the rules depend on the size of your employer:
This is the area I see the most expensive mistakes — people defer Doctor coverage (Part B) thinking they're protected and end up with a permanent 10%-per-year late-enrollment penalty surcharged onto their premium for life. Book a call 4–6 months before your 65th birthday to get the timing right.
The cleanest way to do this is in person. Bring your prescriptions, your doctor list, and your Social Security statement.
Book a call →If you're contributing to a Health Savings Account through work, you must stop contributing the month you enroll in any part of Medicare (including Hospital coverage, Part A). This trips up a lot of people. We can help you time enrollment so the HSA contributions wrap up cleanly.
If you don't enroll during your IEP and you don't have qualifying employer coverage, you can sign up during the General Enrollment Period (January 1 to March 31 each year), with coverage starting July 1. You'll likely owe a Doctor coverage (Part B) late-enrollment penalty — 10% per year delayed, added to your premium permanently. Prescription drug coverage has its own late-enrollment penalty.
If you delayed because you had qualifying employer coverage, you get a Special Enrollment Period when that coverage ends — no penalty. Document it carefully.
One conversation. Plain English. We'll cover Original vs. Advantage, the Supplement question, prescription drug coverage, and how it fits with your current coverage.
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