08/30/2026
📢 Working Past 65? Here’s What You NEED to Know About Medicare.
Thinking about staying on your employer’s health insurance past age 65? It might seem simple, but making a mistake can lead to denied claims and permanent lifetime penalties on your Medicare Part B premium.
Here are the key rules you need to know before turning 65:
🏢 1. The Employer Size Rule: 20 is the Magic Number
19 or fewer employees: Medicare becomes your primary coverage at age 65. You must enroll in Medicare; if you don't, your employer's group plan can deny your claims, leaving you unprotected.
20 or more employees: Your employer group coverage remains primary. You have the choice to keep your work insurance and delay enrolling in Medicare.
🛑 2. Staying on Employer Coverage? Be Careful What You Enroll In…
Hold off on Part B: If your group plan is primary, signing up for Part B means paying an unnecessary monthly premium. Delaying it also protects your future open enrollment rights when you eventually retire.
Beware of Part A if you have an HSA: Even though Part A is premium-free for most, enrolling in it disqualifies you from contributing to a Health Savings Account (HSA). In fact, HSA contributions must stop 6 months prior to enrolling in Medicare to avoid tax penalties.
⚠️ 3. The COBRA & Retiree Insurance Trap
Many people assume COBRA or retiree health plans count as active employer coverage—they do not. If you rely on COBRA instead of enrolling in Medicare at 65, Medicare will assess a 10% penalty for each year you delayed Part B, added to your premium for the rest of your life.
đź“„ 4. Proving Creditable Coverage Later
When you do eventually retire (whether at 68 or 78), Social Security will require an employer coverage form (Form L564) signed by HR to prove you had continuous creditable coverage and waive late enrollment penalties.
👉 Don't let unexpected rules catch you off guard—double-check with your HR department about your plan size and coverage status before your 65th birthday!
