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    Medicare Enrollment Timeline

    Don't miss the windows.

    Initial Enrollment Period (IEP)

    • 3 months BEFORE your 65th birthday month.
    • The month you turn 65.
    • 3 months AFTER 65th birthday month.
    • = 7-month window total.
    • Sign up on time = no penalty.
    • Late = lifetime 10% penalty per year late on Part B.

    If still working at 65

    • If employer covers you (20+ employees) — can delay Part B.
    • Special Enrollment Period 8 months after job ends.
    • Smaller employer (under 20) — Medicare is primary, sign up.
    • Get "creditable coverage" letter from employer for proof.
    • Mistakes here = costly penalties.

    Part D (drugs) timing

    • Same IEP window.
    • Late = 1% lifetime penalty per month late on Part D.
    • Even if no current prescriptions — STILL enroll cheap basic plan to avoid future penalty.
    • Can change plans annually during AEP.

    Annual Enrollment Period (AEP)

    • October 15 - December 7 every year.
    • Switch Medicare Advantage plans.
    • Switch Part D plans.
    • Switch BETWEEN Original Medicare + Medicare Advantage.
    • Changes take effect January 1.
    • Compare every year — plans + drugs + costs change.

    Free help

    • SHIP — State Health Insurance Assistance Program. Free unbiased Medicare counselors. shiphelp.org.
    • 1-800-MEDICARE — free official line.
    • Medicare.gov Plan Finder — compare drugs + plans for your area.
    • SSA.gov/medicare — apply online.
    • Avoid commission-based "Medicare advisors" — biased.

    Most-missed: Medigap window

    Medigap (Medicare Supplement) — best 6-month window starts when you sign up for Part B. After that, insurers can charge more / deny based on health. Don't miss this window.