Still Working at 65? 7 Medicare Questions to Ask Before You Delay Part B

Turning 65 doesn't mean you have to drop your employer coverage and sign up for every part of Medicare right away. Whether you can safely delay Part B depends on a few key details. Here's what to check first.

1. Is your coverage based on current employment?

  1. Coverage through your own or your spouse's current job can qualify you to delay Part B and use a Special Enrollment Period later
  2. COBRA, retiree plans, Marketplace plans, and VA coverage do NOT protect your enrollment timing
  3. Get written confirmation from your employer's benefits department

2. How big is the employer?

  1. 20+ employees: employer plan usually pays first, Medicare pays second
  2. Fewer than 20 employees: Medicare usually pays first, employer plan pays second
  3. Ask HR directly: "Does our plan pay first after I turn 65, or does Medicare?"

3. Do you have an HSA?

  1. You can't contribute to an HSA once Medicare coverage starts
  2. Medicare Part A can be retroactive up to 6 months — this can trigger HSA contribution problems
  3. Coordinate timing with your employer, HSA administrator, and a tax professional before applying

4. Is your drug coverage creditable?

  1. Ask if your employer/union drug plan is "creditable" (pays as well as Medicare Part D on average)
  2. Save every Notice of Creditable Coverage you receive
  3. Going 63+ days without creditable drug coverage can trigger a Part D late penalty

5. When does your coverage actually end?

  1. You generally get 8 months to enroll in Part B after employment or coverage ends (whichever comes first)
  2. Don't wait until the deadline — apply early to avoid a coverage gap
  3. Track: last day worked, last day of coverage, desired Medicare start date, enrollment deadline

6. Are you considering COBRA or retiree coverage?

  1. COBRA does not extend your 8-month Part B Special Enrollment Period
  2. The clock starts when active employment/coverage ends — even if you elect COBRA
  3. Retiree coverage also doesn't count as "current employment" coverage

7. Is everything in writing?

Keep a folder with:

  1. Written proof coverage is based on current employment
  2. Employer size + who pays first
  3. Notice of Creditable Coverage
  4. Planned employment/coverage end dates
  5. HSA contribution and Medicare start dates
  6. Enrollment confirmations
  7. Benefits contact info

Bottom line

Don't auto-enroll in Part B just because you turned 65 — and don't auto-delay it just because you're still working. Confirm your coverage type, who pays first, drug coverage status, HSA impact, and your employer coverage end date first.

Questions are always welcome — I'm just a call or text away: 435-244-2001.

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