Working Past 65
Decide whether to enroll or delay only after the employer plan and HSA consequences are verified.
Decide from employment status, not just an ID card
Medicare’s current-employment rule can allow Part B delay when qualifying group coverage comes from your or your spouse’s present job. Confirm the employer size and whether Medicare or the plan is primary. A small-employer arrangement can make Medicare primary even while you keep working. Do not assume a union, retiree, COBRA or Marketplace policy provides the same protection.
Official source: Medicare: Working past 65 ↗ · Medicare: Who pays first ↗
Mark the eight-month Part B window
The standard active-employment Part B Special Enrollment Period continues while qualifying coverage exists and for up to eight months after employment or that group coverage ends, whichever happens first. COBRA does not extend the clock. Ask SSA for the Part B-only application instructions and needed employment proof before your last workday. Coordinate the requested effective date with the group plan’s end date.
Official source: Medicare: When coverage starts ↗ · Medicare: COBRA coverage ↗ · SSA: Sign up for Part B only ↗
Part A and the HSA
Medicare coverage makes HSA contribution timing a separate issue. SSA explains that Part A may begin retroactively up to six months when a person over 65 signs up later. Contributions attributable to months with Medicare coverage can create tax consequences. Ask a qualified tax adviser to calculate the last contribution and how employer contributions should be handled rather than assuming the Part B delay preserves HSA eligibility.
Official source: SSA: When to sign up ↗ · Medicare: Working past 65 ↗
Keep the drug coverage proof
Ask the employer for its annual written notice stating whether the drug plan is creditable for Part D. Preserve each notice and exact coverage dates. A gap of 63 or more consecutive days after Part D eligibility without Part D or other creditable drug coverage can cause a lasting penalty if you enroll later. A Part B Special Enrollment Period does not itself prove your drug coverage was creditable.
Official source: Medicare: Creditable drug coverage ↗ · Medicare: Part D costs ↗
Before retiring
Request written payer-order and end-date details, choose a Part B start through SSA, review your A/B card, and only then compare Original Medicare with separate Part D and possible Medigap versus an available Advantage plan. Model doctors, medicines, annual costs and future switching rights. Keep an overlap when necessary to avoid a care gap, but verify each policy’s coordination rule rather than assuming double payment.
Official source: Medicare: Who pays first ↗ · SSA: Sign up for Medicare ↗ · Medicare: Original versus Advantage ↗