Your Initial Enrollment Period runs 3 months before to 3 months after your 65th birthday month.
Miss Part B or Part D without other coverage and the penalty is permanent.
Your Initial Enrollment Period is seven months: three before your 65th birthday month, the month itself, three after. Miss it without other creditable coverage and Part B costs 10% more for every year you delayed, for life.
Bring your birth date, whether you or a spouse are still working and for how big an employer, your prescription list, and the doctors you won’t give up. That’s the whole conversation.
I’m Nathan Baughman with BIG Benefits. Medicare is a specialty, and for enrollment I work alongside Justin Kendter of Kendter Insurance Solutions, who is AHIP-certified and does nothing but Medicare and Medicare Supplements. What I can do is make sure the years before 65 are handled right, and that you walk into the Medicare conversation knowing what you’re looking at.
The 2026 numbers. Part B premium $202.90/month, deductible $283. Part A hospital deductible $1,736 per benefit period. Part D out-of-pocket cap $2,100 (rising to $2,400 in 2027). Higher incomes pay more for Part B and D (IRMAA), based on your tax return from two years earlier.
The dates. Annual Enrollment Oct 15 – Dec 7 (for the following year). Medicare Advantage Open Enrollment Jan 1 – Mar 31. General Enrollment Jan 1 – Mar 31 if you missed your IEP.
Before 65: if you’re retiring early, see the Early Retirees page. If you’re on a private plan with me, it’s guaranteed renewable to 65 and we plan the hand-off a year out.
At 65: a call with Justin and me. Timeline, Advantage vs Supplement for your doctors and prescriptions, Part D, and the IRMAA look-back if you had a big income year.
Seven-month window. The 20-employee rule. Stop the HSA six months early. Advantage or Supplement is about your doctors, not the commercial. Medigap is guaranteed only once.
“Spoke with Nathan today… He was a wealth of knowledge and was able to answer all of my questions regarding health insurance plans without skipping a beat.” — Google review
Delaying because you’re still working, without checking the rule. If your employer has 20 or more employees and you’re on their plan, you can delay Part B penalty-free and get an eight-month window when you leave. Under 20 employees, Medicare is primary and you need to enroll at 65. COBRA and retiree coverage don’t count as “still working.
“Contributing to an HSA after Part A starts. Part A enrollment can be retroactive up to six months. Stop HSA contributions six months before you apply.
Choosing Advantage or Supplement on the TV ad. Medicare Advantage: all-in-one, often $0 premium, networks and prior authorizations, an out-of-pocket max (up to $9,250 in-network for 2026). Medigap Supplement: any doctor that takes Medicare, nationwide, no networks, a monthly premium, plus a separate Part D drug plan. In Pennsylvania, your six-month Medigap open enrollment when Part B starts is the one guaranteed-issue window you get; after that they can underwrite you.
1. Is there a maximum out-of-pocket? 2. Is it an unlimited contract? 3. Is it guaranteed renewable? If a plan uses words like “deductible” and “PPO network,” that doesn’t automatically make it actual health insurance. These three questions do.
Send me an age and a zip code and I’ll send back a general idea of what’s available in your area. Twenty minutes, no charge, no pressure. Happy to answer any and all questions so you can make the most informed decision for you, your family, or your business.
