Still Working at 65? Sign Up for Medicare or Wait?

Still working at 65? Medicare does not always mean you should enroll straight away — but waiting can create expensive mistakes if you miss the rule that applies to your employer plan. This video explains the Medicare decision for people still working at 65: the 20-employee line, who pays first, when Part B can wait, why COBRA is different, the Part D deadline, HSA contributions, and the six-month Part A backdating rule. 00:00 Two coworkers, one free benefit 01:52 The 20-employee line 04:12 Linda’s decision — and the question people miss 05:52 Three windows and two different clocks 08:35 The penalty that follows the premium 10:39 Why free Part A can change the math 14:01 Your spouse and your drug coverage 16:22 What the two options actually cost 19:03 The decision map 21:14 One email this week What you’ll learn · When an employer plan usually pays before Medicare · Why the 20-employee threshold matters · Why COBRA and retiree coverage follow different rules · When delaying Part B can be safe — and when it is not · How Part A can affect HSA contributions · Why Part D has a separate 63-day deadline · The one question to send your benefits administrator The practical question is not simply “sign up or wait?” It is: who pays first, which enrollment window applies, and whether Part A, Part B and Part D should be treated separately. Sources · Medicare — Working past 65: https://www.medicare.gov/basics/get-starte... · Medicare — Who pays first: https://www.medicare.gov/health-drug-plans... · Medicare — When can I sign up?: https://www.medicare.gov/basics/get-starte... · Medicare — Avoid late enrollment penalties: https://www.medicare.gov/basics/costs/medi... · CMS — 2026 Medicare premiums and deductibles: https://www.cms.gov/newsroom/fact-sheets/2... · IRS — Publication 969, Health Savings Accounts: https://www.irs.gov/publications/p969 · Medicare — Medigap open enrollment: https://www.medicare.gov/health-drug-plans... Educational content only. Not financial, tax, legal or insurance advice. Medicare rules depend on your employer plan and individual circumstances; check your plan documents and the official sources before enrolling. #Medicare #RetirementPlanning #WorkingPast65