Turning 65 as a CalSTRS or CalPERS member is a different problem — and the premium you pay in 2026 was decided by your 2024 tax return.

Most Medicare guides assume you spent forty years paying FICA and will claim Social Security at 65 alongside Part B. Many California educators did neither — and the standard playbook quietly breaks in four places.

No Social Security? You still get Medicare. Most CalSTRS teachers didn’t pay into Social Security — but Medicare tax is a separate line. If you paid Medicare tax for 10+ years (most educators hired after April 1986 did), you qualify for premium-free Part A at 65. If your service predates that, you may still qualify through a spouse’s work record. The enrollment mechanics also change: with no Social Security check to deduct from, Part B is billed to you directly — nothing happens automatically, which makes the windows below entirely your responsibility.

CalPERS members have a mandatory handoff. CalPERS requires enrolling in a CalPERS Medicare health plan when you turn 65 to keep your retiree coverage — your CalPERS plan then wraps around Medicare rather than replacing it. Miss the window and you can lose the subsidy. This is a coordination problem, not a shopping problem: the CalPERS enrollment, the Medicare enrollment, and the pension start date have to land in the right order.

District retiree health benefits vary wildly. Some districts pay retiree medical to 65, some to Medicare age, some for life — and the answer often turns on hire date and bargaining unit. We read your collective-bargaining language as part of the plan, before you pick a retirement date, because a date moved by one school year can change what the district owes you for a decade.

The enrollment windows are unforgiving. Your Initial Enrollment Period is the 7 months around your 65th birthday. Late Part B enrollment costs a 10% premium penalty per full year missed — and the penalty is permanent, compounding every future year’s premium including any IRMAA on top of it. If you’re still covered by active employer group coverage at 65, a Special Enrollment Period protects you — but retiree coverage does not count as active coverage, which is precisely the distinction that catches educators who retire at 62.

And the gap years before 65 are their own problem. Retire at 60 with a CalSTRS pension and you have up to five years of bridge coverage to arrange — district retiree medical if you have it, a spouse’s plan, or an individual policy. The bridge premium belongs in the retirement-income math from the start; it is frequently the largest single expense between the last paycheck and Medicare, and it moves the “can I afford to retire at 60” answer more often than the portfolio does.

The underwriting point deserves its own sentence, because it is the one that doesn’t reverse: outside your initial window, moving from Medicare Advantage back to a Medigap policy generally requires passing medical underwriting — and the years when you most want Medigap’s freedom of doctor are the years you are least likely to pass. The $0 premium is real; so is the one-way door behind it.

One more thing no one tells you: Medicare does not cover long-term care — the largest unfunded risk in most retirements. That’s a separate plan: see Long-Term Care & the 6 ADLs for the trigger, the costs, and the three ways to fund it.

We don’t sell Medicare plans. We build the retirement plan so that Medicare’s rules — the lookback, the windows, the wrap-around — work for you instead of against you.

• IRMAA-aware withdrawal sequencing — which account you draw from, in which year, decides your premium two years later. The sequence is designed with the $109K/$218K cliffs on the page.
• Roth conversion timing — we model conversions against the IRMAA tiers so one good tax idea doesn’t become a Medicare surcharge. Sometimes the answer is the same conversion, split across two years.
• Retirement-date coordination — aligning your district benefits, the CalSTRS/CalPERS start, the bridge coverage, and the 7-month Medicare window into one calendar.
• Appealing IRMAA — retirement is a qualifying life-changing event; form SSA-44 can reset your surcharge to your new, lower income. We prepare it as part of the first Medicare year, not as an afterthought.