How is the Working Past 65: Delay Decision calculated?

Whether it's safe to delay Medicare while working past 65 turns on a small set of published rules: who pays primary (which hinges on employer size), the HSA six-month lookback, and the 8-month Special Enrollment Period after employment coverage ends. We apply those rules to your answers and return a verdict with the reasons.

What data and assumptions does it use?

Medicare.gov — "Working past 65" and "How Medicare works with other insurance" (coordination-of-benefits rules). CMS "Medicare & Other Health Benefits: Your Guide to Who Pays First". IRS Publication 969 (HSAs and Medicare enrollment).

Readiness

Working Past 65: Delay Decision

Plan with confidence.

Tell us a little about you

Estimates are fine — you can fine-tune the result after.

Employer size

The size of the employer whose plan covers you (yours or your spouse’s). This one fact flips who pays first.

Contributing to an HSA?

Health Savings Account contributions and Medicare don’t mix — enrolling ends your eligibility to contribute.

Months until you plan to retire

When the employer coverage would end.

What you’ll learn

Employer of 20 or more: the employer plan pays primary, so delaying Part B while covered is generally penalty-free — you get an 8-month Special Enrollment Period when employment coverage ends.
Employer of fewer than 20: Medicare pays PRIMARY at 65 even if you stay on the employer plan — without it the plan may pay almost nothing, so the verdict is to enroll now.
HSA contributions: enrolling in Medicare (even just Part A) ends HSA eligibility, and Part A can start retroactively — so contributions should stop about six months before it begins.
Retiring within a few months: delay buys little and the enrollment clock is about to start, so the verdict flags the delay as risky and points at the timeline instead.

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