Official checklist
Apply for Medicare · United States
Verified against Social Security Administration / Medicare on May 22, 2026.
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Bring these documents
Step by step
Mark your 7-month Initial Enrollment Period (IEP)[3]
Runs from 3 months BEFORE the month you turn 65 through 3 months AFTER. Enrolling in the first 3 months means coverage starts the month you turn 65. Enrolling later delays the start date by 1–3 months.
Decide whether you'll take Part B now or delay it[8]
If you have credible employer coverage from current employment (yours or spouse's), you can delay Part B without penalty via the Special Enrollment Period — sign up within 8 months of losing that coverage. If you have NO credible coverage, delaying Part B triggers a 10% per year LIFETIME late-enrollment penalty.
Enroll online if you're not already receiving Social Security[2]
If you're already getting Social Security benefits, you're auto-enrolled in Parts A and B 3 months before age 65. If not, enroll yourself at ssa.gov/medicare — takes about 20 minutes.
Pick your coverage structure: Original Medicare vs. Medicare Advantage[9]
Original Medicare (Parts A + B): see any provider that accepts Medicare; add Part D for drugs and Medigap for cost-sharing protection. Medicare Advantage (Part C): private all-in-one plans with networks; usually include drug coverage and extras like dental / vision. Choose during the same window as Part B enrollment.
Sign up for Part D (prescription drugs) within your IEP[10]
Part D is the prescription drug benefit, sold by private insurers. Missing your IEP triggers a 1% per month LIFETIME late-enrollment penalty. Use Medicare.gov's plan finder to compare based on YOUR specific drug list.
Consider Medigap (Medicare Supplement) immediately if going Original Medicare[11]
Medigap has a 6-month one-time guaranteed-issue window starting when you're 65 AND enrolled in Part B. Miss it and insurers can medically underwrite or refuse coverage in most states. Pricing varies dramatically — shop multiple carriers.
Common reasons this gets rejected
Missing the Initial Enrollment Period and getting hit with lifetime penalties
Part B late penalty: 10% per FULL year you delayed, added to your premium for LIFE. Part D late penalty: 1% per month delayed, also lifetime. These penalties compound over decades of retirement.
Assuming COBRA counts as credible coverage
COBRA is NOT credible coverage for Medicare purposes. If you go on COBRA at 65 and skip Part B, you'll hit the penalty when you finally enroll. Sign up for Part B even if you have COBRA.
Not signing up for Medigap within the 6-month guaranteed-issue window
Medigap is medically underwritten in most states after the 6-month window. Pre-existing conditions can make it unaffordable or unavailable. Enroll in Medigap immediately after Part B.
Going with the cheapest Part D plan without checking YOUR drug list
Plans vary wildly on which drugs are on formulary and at what tier. The cheapest premium might charge 10x more for your specific medications. Always run YOUR drug list through Medicare.gov's plan finder.
Trusting a high-pressure agent or 'free' advisor
Medicare insurance agents earn commissions on private plans (Advantage, Medigap, Part D). Use Medicare.gov's plan finder yourself before talking to anyone — that's the unbiased source.
Talk to a human
Sources
- [1]Medicare basics
- [2]Apply for Medicare
- [3]When can I sign up?
- [4]Plan Compare (Part D / Medicare Advantage / Medigap)
- [5]Medicare costs
- [6]State Health Insurance Assistance Program (SHIP) — free local counseling
- [7]https://www.cms.gov/medicare/cms-forms/cms-forms/downloads/cms-l564e.pdf
- [8]https://www.medicare.gov/basics/costs/medicare-costs
- [9]https://www.medicare.gov/your-medicare-costs/get-help-paying-costs
- [10]https://www.medicare.gov/drug-coverage-part-d
- [11]https://www.medicare.gov/health-drug-plans/medigap
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Last verified: May 22, 2026 · Spot something wrong? Report a correction →