Medicare 2027: The Deadline Mistake You MUST Avoid at 65

Choosing the wrong Medicare start date at age 65 can trigger permanent penalties that follow you for the rest of your life. Even if your HR department, co-workers, or friends tell you that you can "wait," hidden traps—like the 6-month HSA lookback penalty and the COBRA illusion—are catching thousands of new retirees off guard heading into 2027. In this video, we break down the exact deadlines you must hit to guarantee you never pay a late fee. ✅ Subscribe to MedicareHub for essential 2027 timing updates that protect your retirement. 💬 Comment Below: Are you turning 65 soon or working past 65? Tell us your target retirement date! 📢 Share this video with a co-worker who is planning to retire this year. The High-Stakes Truth Inside This Video: The One Wrong Date: Why misunderstanding your 7-month Initial Enrollment Period (IEP) can leave you uninsured for up to 8 months. The 6-Month HSA Landmine: Why enrolling in Part A automatically backdates and causes severe IRS tax penalties if you didn't stop contributions in time. The 20-Employee Threshold: The strict rule that dictates whether your employer plan pays first or if Medicare demands to be primary at 65. The COBRA Trap: Why COBRA is NOT considered "creditable coverage" by Medicare and quietly triggers lifetime Part B and Part D penalties. The 63-Day Prescription Clock: Why you only have 63 days after leaving work to secure Part D drug coverage before compounding monthly fines begin. What HSA/HRA Funds CANNOT Pay: The strict federal rule prohibiting you from using health accounts to pay for private Medigap premiums. ⏱️Timestamps: 0:00 - Avoid Costly Medicare Enrollment Mistakes 0:51 - Understanding the Initial Enrollment Period 3:06 - Medicare Part A Entitlement Rules 4:20 - HSA Contribution Rules and Penalties 6:43 - Differences Between HSAs and HRAs 8:02 - Backdating Part A and HSA Risks 9:08 - Eligible Expenses for HSA and HRA Funds 11:54 - Employer Size Rules: Large vs. Small Groups 13:38 - Why COBRA Is Not Creditable Coverage 14:52 - Avoiding Part B and Part D Penalties Need Personalized Help? Call us at ☎ 1-855-230-4205 Schedule a FREE Medicare timing review with our licensed experts and get clear answers for your specific situation: https://www.medicarehub.org/