Miss This Medicare Deadline and You’ll Pay a Penalty for Life

Miss This Medicare Deadline and You’ll Pay a Penalty for Life David Beren Fri, June 12, 2026 at 9:36 PM GMT+7 6 min read Quick Read Missing Medicare s Initial or Special Enrollment Period triggers a permanent Part B surcharge, and neither COBRA nor retiree coverage offers any protection against it. A three-year enrollment delay locks in a permanent 30% surcharge on the $202.90 monthly Part B premium, recalculated upward every year premiums rise. At employers with fewer than 20 workers, Medicare becomes the primary payer at 65, so skipping Part B creates both a permanent penalty and uncovered costs. Many financial professionals are salespeople paid on what they push, not whether you end up wealthier. A fiduciary is the opposite. The SEC legally requires them to put your interests first. Advisor.com s free matching tool pairs you with vetted fiduciaries from firms like Vanguard, Empower, and Edelman — in under three minutes. See who you match with today. Medicare s Part B and Part D late-enrollment penalties are permanent surcharges that attach when someone eligible for Medicare fails to enroll on time without qualifying coverage during the gap. COBRA and retiree coverage do not protect against the Part B penalty, and the eight-month Special Enrollment Period that follows the end of active employer coverage runs independently of any COBRA election. Miss both the Initial Enrollment Period and the SEP, and you generally wait for the next General Enrollment Period to get Part B, with the surcharge applied for life. This article is for anyone approaching 65, or already past it, who is still on an employer plan, retiree coverage, COBRA, or no coverage at all. If you enrolled in Part B on time, skip it. Everyone else faces a narrow set of dates that decides whether they pay a permanent Medicare surcharge for the rest of their lives. The Initial Enrollment Period is a seven-month window around your 65th birthday: the three months before the birthday month, the month itself, and the three months after. Part B and Part D penalties start accruing the moment that window closes, unless you qualify for a Special Enrollment Period. The SEP exists only for people covered by a group health plan based on current active employment, their own or a spouse s, at an employer with 20 or more employees. It runs for eight months after that employment or the group coverage ends, whichever comes first. COBRA, retiree coverage, and Affordable Care Act marketplace plans do not count as creditable coverage for Part B. So for someone whose employer coverage ended in January and who then spent 18 months on COBRA, the SEP clock started in January. The fall Annual Enrollment Period, October 15 to December 7, only lets current enrollees change Medicare Advantage and Part D plans. The window that lets someone who missed the IEP and SEP enroll in Part B is the General Enrollment Period, January 1 through March 31, with coverage starting the month after enrollment. The penalty attaches then and stays. The Part B penalty adds 10% of the standard premium for every full 12-month period you were eligible but not enrolled, and it rides your premium for as long as you hold Part B, which for most people means life. CMS recalculates it each year against the current standard premium, so it climbs as premiums rise. A three-year delay locks in a 30% surcharge, hundreds of dollars a year on top of the standard premium and thousands over a decade, more as the premium keeps rising. Most Americans suspect they re behind on retirement and never find out. Advisor.com s free matching tool pairs you in about three minutes with a vetted fiduciary advisor who can help you with investing, taxes, retirement, estate planning, and more. No minimums. No sales call. Find out where you stand. The Part D penalty runs on a monthly clock instead. It adds 1% of the national base beneficiary premium for every month you went without creditable drug coverage after your IEP closed. Two years without coverage produces a 24% surcharge on top of whatever plan you eventually pick. The dollar amount is smaller than the Part B penalty, but it follows the same rule: permanent, recalculated each year against the current base premium, and paid on top of the plan s own premium. Creditable coverage for Part D has a separate definition from creditable coverage for Part B. A retiree drug plan or a VA prescription benefit can count as creditable for Part D, sparing you that penalty, even though the same retiree coverage does nothing against the Part B penalty. Plans must send an annual creditable coverage notice, and keeping those notices matters, because the burden of proof later falls on you. Working past 65 at a small employer carries its own risk. At employers with fewer than 20 employees, Medicare is generally the primary payer at 65, whatever the group plan says. Skip Part B there and you can end up paying out of pocket for what Medicare would have covered, and still accruing

Miss This Medicare Deadline and You’ll Pay a Penalty for Life

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