The Turning 65 Checklist

Start about six months out

Find out whether you will be automatically enrolled. If you are already drawing Social Security benefits, Parts A and B usually start on their own. If you are not, nothing happens until you sign up, and that is where most penalties come from.

Your window is seven months long

It opens three months before the month you turn 65, includes your birthday month, and closes three months after. Enrolling in the three months before your birthday month generally gets coverage started soonest. Waiting until after your birthday month can push your start date back.

If you are still working

Employer coverage changes the math, and whether it does depends largely on how many people your employer has. For some people the right move is to delay Part B without penalty. For others, delaying is a costly mistake. This is the single most common place people get bad advice from a well-meaning friend.

Before you choose anything

• Write down every prescription with its dose. Plans cover different drugs at different tiers.
• List the doctors you want to keep, and the hospital you would want to use.
• Decide how much you travel, and whether you spend part of the year in another state.

The deadline that follows you

The Part B late enrollment penalty is not a one-time fee. It is added to your premium for as long as you have Part B. Confirming your dates takes ten minutes and it is the highest-value thing on this list.