Medicare enrollment has real deadlines with real consequences for missing them. A late enrollment penalty for Part B or Part D follows you for life — added permanently to your premium. This checklist walks you through every step so nothing slips through.
Your Initial Enrollment Period begins. If you want Medicare to start on your 65th birthday, you must enroll before the month you turn 65. Contact Social Security (online at ssa.gov or by calling 1-800-772-1213) to sign up for Part A and Part B.
Still working and covered by employer insurance? You may be able to delay Medicare without penalty — but only if you or your spouse is still actively employed (COBRA, retiree plans, and marketplace plans do NOT count). Verify with your HR department and a Medicare advisor before deciding to delay.
Before choosing a plan, make a list of: all your current medications (name, dose, frequency), your primary care doctor and any specialists, preferred hospitals or health systems, and your current monthly healthcare costs.
This is the biggest decision. Original Medicare gives you maximum doctor choice nationwide. Medicare Advantage bundles everything with a cost cap, tied to a local network. Your medications, providers, and how much you travel all affect which fits better.
Your 6-month Medigap open enrollment window starts the month you turn 65 and are enrolled in Part B. During this window, insurers cannot deny you coverage or charge more based on health conditions. After it closes, you may be subject to medical underwriting — and could be declined. This window doesn't come back.
Whether you choose Original Medicare or Medicare Advantage, make sure drug coverage is in place. If you choose Original Medicare, add a standalone Part D plan. If you choose Medicare Advantage, confirm it includes drug coverage. Delaying Part D without other creditable drug coverage adds a permanent penalty to your premium.
If your income is limited, you may qualify for Extra Help (lowers Part D costs), a Medicare Savings Program (may pay your Part B premium), or Medicaid coordination. These programs can save thousands per year — and many people who qualify don't know they do.
Medicare plans can change premiums, formularies, networks, and benefits every January. Set a reminder to review your coverage each October 15–December 7. What was the best plan last year may not be best this year.
A PharmSurance advisor can guide you through every step on this list — check your medications, compare plans in your area, and help you enroll correctly. At no cost to you.
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