I’m retiring halfway through the month. How do I make sure I’m covered?

Start by getting the exact date your employer insurance ends. Your last day at work and your last day of insurance may be different. Then arrange Medicare to begin without a gap between the two.

If you’re enrolling after 65 through the Special Enrollment Period for employer coverage, Part B generally starts on the first day of a month. Social Security says the start can vary with when you apply, so confirm the date you’re requesting rather than assuming coverage will begin the day after you retire.

For example, if your employer confirms coverage ends November 15, ask Social Security about a November 1 Medicare start. That overlap could avoid an uninsured second half of November. This is a planning example, not a promise that an application will be approved for that date.

Confirm the start dates for your drug plan and any Medigap or Medicare Advantage coverage too. If you or your spouse contribute to an HSA, resolve the contribution timing before applying.