Working past 65

Picking your retirement date: a sequencing problem, solved

Retiring after 65 is a sequencing problem: stop HSA contributions six months out, get the L564 signed ~90 days out, file for Part B to start the day after employer coverage ends, let TFL or CHAMPVA wake up on that date — or open the Medigap window if you're VA-only — and handle IRMAA's stale-income surcharge with SSA-44.

The master timeline

When	Do	Why
T−6 months	Last HSA contribution (if contributing)	Part A backdates six months; prorate the final-year limit
T−3 months	CMS-L564 to HR; file CMS-40B with your requested start date	HR turnaround is the bottleneck; the SEP guide has the steps
T−2 months	TFL/CHAMPVA: confirm DEERS / other-coverage records; VA-only: gather Medigap quotes or MA comparisons	The wraparound starts when B does; the Medigap window opens then too
T−1 month	Decide the drug routing for retirement	Employer column disappears — re-run the three-way comparison; CHAMPVA households reclaim Meds by Mail once no other drug coverage remains
T (last day)	Employer coverage ends; Part B effective next day	Zero-gap handoff — TFL/CHAMPVA active immediately
T+1 to +6 months	VA-only: execute the Medigap or MA decision inside the window; everyone: SSA-44 if IRMAA priced you on working income	The window never reopens; the surcharge appeal does

Choosing T itself — the honest variables

The younger-spouse bridge. Often the real constraint — price it first.
IRMAA's two-year lookback. Retiring in January vs. December changes which tax year sets which premium year. A fat final year plus severance can buy a surcharge tier; SSA-44's "work stoppage" event is the remedy, but timing income (deferring a bonus, splitting a payout) avoids needing one.
The mid-year HSA wind-down. A December 31 retirement makes the six-month rule trivial; a June 30 one makes it arithmetic.
End-of-month coverage quirks. Most employer plans run through the final month — Part B effective the 1st of the following month meets it cleanly. Confirm yours doesn't end on the last worked day.

What you're retiring into, by program

TFL: arguably an upgrade — the wraparound most working plans can't match. CHAMPVA: same shape, plus free generics return. VA-only: the one group with a genuine open decision (OM + Medigap vs. OM alone vs. MA) — which is why your T−2 homework matters most.

Bring an agent your retirement date and the four household dates, and the entire table above becomes a filled-in calendar — free, in one sitting.

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Or compare plans yourself at PlanMatch.com, or contact Medicare.gov / 1-800-MEDICARE.

Frequently asked questions

When should Part B start relative to my last day of work?

The day after your employer coverage ends — typically the 1st of the month after your last covered month. File 40B/L564 with that requested date about 90 days out.

Will my Medicare premium reflect my working income?

Initially yes — IRMAA uses the tax return from two years prior. After retirement drops your income, SSA-44's life-changing-event appeal resets the surcharge to current reality.

Should I retire in December or January?

Tax and IRMAA mechanics often favor January (a clean final tax year, easy HSA math), but the spouse bridge and plan-year deductibles can argue otherwise. It's a worksheet, not a rule.

Does my TRICARE for Life start automatically when I retire?

It starts when Part B does — which you control via the SEP filing. Sequence B to the day after employer coverage ends and TFL is seamless.

You earned these benefits. Make them work together.

Whether you keep exactly what you have or add Medicare coverage alongside it, the right answer depends on your health, budget, and how you like to get care.

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No cost, no obligation. You can also get help from Medicare.gov, 1-800-MEDICARE (TTY 1-877-486-2048), or your local SHIP office.