The Medicare paperwork after 65, explained in plain English and filled in correctly.
Two situations trip up a lot of people around retirement: signing up for Part B when employer coverage ends, and paying a higher Medicare premium (IRMAA) based on income from before you retired. Each tool gives you a free answer first. If you want the forms filled in for you, that's $39.
Leaving employer coverage
Part B Special Enrollment check
Worked past 65 with a job-based health plan? Find out if you qualify for the Special Enrollment Period, the exact last day of your 8-month window, whether COBRA or retiree coverage puts you at risk of a lifelong penalty, and which forms you need.
Kit ($39): CMS-40B and CMS-L564 filled in, employer instructions, proof checklist if your employer won't sign, cover letter, submission steps.
Retired and paying IRMAA
IRMAA SSA-44 check
Social Security sets IRMAA from your tax return of two years ago. If you stopped working or had another life-changing event, see whether you qualify to have it recalculated, your current and likely new tier, and the yearly savings.
Kit ($39): SSA-44 filled in, evidence checklist for your event, cover letter, how to submit and what happens next.
Part B enrollment guides
- The Part B Special Enrollment Period: who qualifies and how the 8 months work
- How to fill out CMS-L564: Section A and Section B, line by line
- Employer won't (or can't) sign CMS-L564? What Social Security accepts instead
- CMS-40B instructions: how to fill out the Part B enrollment request
- COBRA and Medicare Part B: why COBRA doesn't extend your deadline
- The Part B late enrollment penalty: how it's counted, with worked examples
- When does Part B start if you sign up during the Special Enrollment Period?
- How to submit CMS-40B and CMS-L564: online, by fax, by mail or in person
- Retiree health coverage and Medicare Part B: why it doesn't let you wait
- Working past 65 at a small employer: Medicare pays first, but you still get the SEP
IRMAA guides
- How IRMAA is calculated: MAGI, the 2-year lookback and the tiers
- IRMAA brackets 2026: the full Part B and Part D tables
- IRMAA brackets 2027: what's known so far
- How to fill out SSA-44 step by step
- SSA-44 for retirement: using the work stoppage event to lower IRMAA
- Got an IRMAA letter? What it means and what to do
- IRMAA life-changing events: the 8 that qualify, and what doesn't
- IRMAA appeal vs. SSA-44: which one do you need?
How we work
- Every rule and number comes from Social Security (POMS), CMS or Medicare.gov, and we list the source and the date we checked it.
- We use the official, current government forms and fill them in your browser. Your answers are not stored on our server.
- We never ask for your Social Security or Medicare number. You write those in by hand before you sign.
- Not helpful? One click refunds you within 14 days.