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Check for the retirement mistakes that cost real money
Medicare, Social Security, taxes and health coverage each have their own rules. The expensive mistakes happen where they collide. Answer a few questions and see which ones apply to you.
Or send a questionFree consultation. No obligation to enroll.
The traps it checks
Can COBRA cause a Medicare penalty?
Yes. Only coverage from a current job lets you delay Part B. Your 8-month window to sign up starts when the job ends, even if you choose COBRA. Miss it and the Part B late penalty is 10% for each full year, usually for as long as you have Part B.
When should I stop contributing to my HSA before Medicare?
Six months before you apply for Medicare or Social Security. If you sign up after 65, Part A can start up to 6 months before you apply, and HSA contributions during those months can bring a tax penalty.
Can a Roth conversion raise my Medicare premium?
It can. Medicare's income-related surcharge (IRMAA) uses your tax return from two years earlier, so a large conversion this year can raise your Part B and Part D premiums two years from now.
And a few more
Your first sign-up window, small-employer coverage where Medicare pays first, Marketplace savings that end with Part A, the one-time Medigap window, lowering a surcharge after retirement or a spouse's death, and Social Security held back when you work while collecting before full retirement age. Each result links to the official source and to a plain-English guide like how the Part B penalty works.
This tool is educational. It doesn't recommend a plan, and it isn't tax or legal advice. Surcharge estimates use 2026 Medicare brackets, which change every year. Rules checked against Medicare.gov, HealthCare.gov and the Social Security Administration on November 5, 2026.