In SituationsView all situations →
Here's what you actually have to decide — and the two deadlines that matter right now. You don't need to memorize Medicare. You need to know your next step.
What's actually happening
Around the month you turn 65, a short series of decisions open up — and two of them carry deadlines that can quietly cost you for the rest of your life if you miss them. The good news: almost everything else can wait. We'll keep this to what matters right now.
The two deadlines that matter now
Window 1 · Enrollment
A 7-month window — the 3 months before your birthday month, the month itself, and the 3 after. Enroll in Part B in this window or you can face a lifetime late penalty added to your premium. Most people apply through Social Security online — it takes about 10 minutes.
Window 2 · Protection
A one-time 6-month window (once you're 65 and on Part B) to buy a Supplement with no health questions asked. Miss it, and insurers can charge you more — or turn you down — later.
The decision underneath it all
That's exactly what Fern is for. Describe your situation in your own words — Fern sorts what matters and tells you what to verify next. Not a sales tool. Not a plan picker.
Talk it through with Fern →Still working past 65 with employer coverage? You can skip most of this — that's a different path, with different deadlines.
See "Leaving work coverage" →Want free, unbiased help from a local counselor? Find your SHIP counselor — the State Health Insurance Assistance Program is federally funded and has nothing to sell.
You can ask Fern a question in plain language, find the path that fits your situation, or get the Sunday Letter — one note a week, no pressure.
Not ready to dive in? Get the Sunday Letter · Read the first chapter free