When to Enroll in Medicare (Even If You're Still Working)

Your Initial Enrollment Period (IEP) starts three months before your 65th birthday month and ends three months after — seven months total. If you're not covered by qualifying employer insurance during this window and don't enroll, you'll face a Part B late penalty of 10% for every 12 months you delayed, added to your premium for life.

If you're still working at 65

If your employer has 20+ employees and offers a group health plan, you can generally delay Part B without penalty. When employment or coverage ends, you get an 8-month Special Enrollment Period. If your employer has fewer than 20 employees, Medicare typically becomes primary and delaying Part B usually creates a penalty.

Original Medicare vs. Medicare Advantage vs. Medigap

Original Medicare (Parts A and B) covers roughly 80% of approved costs with no out-of-pocket cap. Most people add either a Medicare Advantage plan (bundles A, B, D and often extras with an out-of-pocket cap and a network) or a Medigap policy (fills the 20% gap in Original Medicare, keeping any-doctor access). Which one fits you depends on doctors, prescriptions, travel, and budget.

What to do six months before 65

Get a plan comparison done — free — with an independent broker. You'll want to see how each option treats your specific doctors and prescriptions. Waiting until the month you turn 65 usually means rushed decisions.