Why working past 65 changes everything
Most people think Medicare enrollment is automatic at 65. But if you have employer coverage through your own job or your spouse's job, the rules change significantly. Making the wrong move can result in lifetime penalties, gaps in coverage, or unnecessary costs.
The key question: Does your employer (or your spouse's employer) have 20 or more employees? This single fact determines whether your employer plan or Medicare pays first — and whether you can safely delay enrollment.
Guides for every situation
Employer coverage + Medicare
How the 20-employee rule works, when employer plans pay first, and the COBRA trap that catches many retirees.
HSA and Medicare
The 6-month Part A lookback rule, when to stop HSA contributions, and how to avoid tax penalties.
Part B Special Enrollment Period
Your 8-month window to enroll penalty-free after employer coverage ends. Plus Form CMS-L564.
Part D creditable coverage
How to verify your employer drug coverage is creditable and avoid the Part D late penalty.
Spouse on employer plan
What happens when one spouse retires and the other keeps working. Coverage coordination rules.
Retiring at 66, 67, 68, or 70
A step-by-step Medicare enrollment timeline based on your planned retirement age.
Common mistakes Colorado workers make
These are the most frequent errors we see among Coloradans working past 65:
- Assuming COBRA counts as employer coverage — It doesn't. COBRA does not qualify you for a Part B Special Enrollment Period. If you choose COBRA at 65+, you must also enroll in Medicare.
- Continuing HSA contributions after enrolling in Part A — Part A is retroactive 6 months. If you enrolled in Part A, you must stop HSA contributions 6 months before your Part A start date or face tax penalties.
- Missing the 8-month Part B SEP window — After your employer coverage ends, you have exactly 8 months to enroll in Part B without a penalty. Miss it, and you'll wait for General Enrollment (Jan-Mar) with coverage starting July 1 — plus a permanent penalty.
- Not checking Part D creditable coverage — Your employer must send you a notice each year stating whether their drug coverage is "creditable." If it's not, you need Part D to avoid a penalty.
Colorado-specific note: Colorado has a significant federal workforce — Denver Federal Center, Buckley Space Force Base, NOAA, USGS, and more. If you're a federal employee, see our FEHB + Medicare guide for rules specific to the Federal Employee Health Benefits program.
Talk to an agent who understands working past 65
The coordination between employer coverage and Medicare is one of the most complex areas of Medicare planning. A licensed Medicare agent can review your specific situation — employer size, spouse coverage, HSA, retirement timeline — and create a personalized enrollment plan at no cost to you.