Turning 65? Your Medicare window is seven months long.
Sign up late and Medicare can add penalties that last as long as you have the coverage. The checklist shows what to do and when, in plain English, and I am glad to walk through your own dates with you.
- What to gather six months outThe information that makes every later decision easier.
- When to sign up for Part A and Part BIncluding what to check if you are still working.
- When a Supplement company cannot turn you downYour six-month Medigap Open Enrollment Period, and how to use it.

Mike Webb, Owensboro born and raised, with more than 16 years in the insurance industry. Licensed in Kentucky, NPN 17036463.
Three dates that decide a lot
- Three months before your birthday month
Initial Enrollment Period opens
Your seven-month window to sign up for Part A and Part B.
- The month you are 65 and Part B starts
Medigap Open Enrollment begins
Six months when a Supplement company cannot turn you down or charge more because of your health.
- October 15 to December 7, every year
Annual Enrollment
Your yearly chance to change Medicare Advantage or Part D plans.
Before you call
Do I have to sign up for Medicare if I am still working?
Not always. If you have group health coverage through your own or your spouse’s current job, you may be able to delay Part B without a penalty. COBRA does not count. The details depend on the coverage, so confirm before you decide.
Is Medicare automatic at 65?
If you already get Social Security benefits, you are usually enrolled in Part A and Part B automatically. If not, you sign up through Social Security.
What does a sit-down with Mike cost?
Nothing, and there is no obligation to enroll in anything.