Turning 65 in Wisconsin: Your 90-Day Medicare Checklist

If your 65th birthday is coming up, Medicare enrollment is probably somewhere on your mind — and probably a little confusing. The good news: if you know your timeline, signing up correctly is straightforward. Here's the checklist Brad walks Wisconsin clients through every week.

Your Initial Enrollment Period Window

Your Initial Enrollment Period (IEP) is seven months long: it starts three months before the month you turn 65, includes your birthday month, and runs three more months after. Miss this window without other creditable coverage, and you risk a permanent late-enrollment penalty on Part B and Part D.

90 Days Before Your Birthday Month

This is the ideal time to start. Create your account at ssa.gov if you don't already have one, decide whether you'll take Part B right away (most people should, unless you have active employer coverage), and start comparing Medicare Advantage versus Medicare Supplement so you're not deciding under pressure.

The Month You Turn 65

Enroll in Part A and Part B through Social Security if you haven't already (Part A is premium-free for most people who worked 40+ quarters, so there's rarely a reason to delay it). Then choose your path: a Medicare Advantage plan bundled with Part D, or Original Medicare paired with a Medicare Supplement policy and a standalone Part D plan.

After Your Birthday — Don't Wait Too Long

You have three more months to finish enrolling, but waiting has a real cost. Medicare Supplement policies come with the strongest guaranteed-issue protections during your first 6 months on Part B — after that, insurers in Wisconsin can medically underwrite you and deny coverage or charge more based on health history. If a Supplement is part of your plan, enrolling early matters.

Medicare Advantage or Medicare Supplement? Wisconsin's Choice Looks a Little Different

Wisconsin doesn't use the standard lettered Medigap plans you'll read about in national articles (no "Plan G" here) — the state uses its own Basic Plan plus optional riders. That's a good reason to talk through the decision with someone licensed in Wisconsin specifically, rather than relying on generic national advice that doesn't apply to your state.