Skip to main content
Jenkins Insurance & Retirement is a private insurance practice not affiliated with or endorsed by the U.S. government or the federal Medicare program.
All Articles
Enrollment

Turning 65? Here's Your Complete Medicare Checklist

Your 7-month Initial Enrollment Period starts 3 months before your birthday month. Here's exactly what to do — and when — so you don't miss deadlines or trigger permanent penalties.

By Jordan Jenkins, Licensed Insurance Advisor, Wyoming & UtahApril 1, 20255 min read

Your Initial Enrollment Period (IEP)

You have a 7-month window to enroll in Medicare Parts A and B around your 65th birthday: the 3 months before your birthday month, your birthday month itself, and the 3 months after. Miss this window without qualifying employer coverage, and you'll face permanent late enrollment penalties on both Part B and Part D.

Timing matters: if you enroll in the 3 months before your birthday month, coverage starts on the first of your birthday month. If you enroll in your birthday month or after, there's a 1–3 month delay before coverage begins. Enrolling early avoids any gap.

3 Months Before Your Birthday Month

Start your research. Make a list of every prescription you take and look up whether it's covered on various Part D plan formularies. Identify your primary care doctor and any specialists you see regularly, then check whether they participate in local Medicare Advantage networks.

Request quotes for Medicare Supplement plans from multiple carriers — the coverage is standardized by plan letter, so comparing prices is straightforward. Use Medicare.gov's Plan Finder tool to explore Part D and Medicare Advantage options in your county.

If you have an employer health plan, contact HR and confirm in writing whether your coverage is 'creditable' for Medicare purposes. This documentation protects you if your enrollment timing is ever questioned.

2 Months Before: Apply for Parts A and B

Apply for Medicare Parts A and B through Social Security. You can do this online at ssa.gov, by calling 1-800-772-1213, or in person at your local Social Security office. If you're already receiving Social Security retirement benefits, you're typically enrolled automatically — but confirm this.

If you have employer coverage you plan to keep past 65, and it's creditable, you can delay Part B enrollment without penalty. However, you'll still want to enroll in Part A if it's premium-free for you (which it is for most people), since it covers hospital care and has no downside to having.

1 Month Before: Choose Your Supplement or Advantage Plan

Once your Medicare card arrives with your effective date, finalize your plan selection. For a Medigap plan, apply directly with the insurance carrier of your choice — you're in your Open Enrollment Period, so you cannot be denied or charged more due to health conditions. For Medicare Advantage, enroll through Medicare.gov or by calling the plan directly.

If you're choosing Medigap, also enroll in a standalone Part D prescription drug plan during your IEP. Part D Open Enrollment also runs concurrent with your IEP, so you won't face a penalty for enrolling now.

After Your Coverage Starts

Review your first Medicare Summary Notice (MSN) — the quarterly statement Medicare mails showing what was billed and paid on your behalf. Check it for errors or duplicate billings.

Schedule your one-time 'Welcome to Medicare' preventive visit within your first 12 months of Part B. It's fully covered and helps establish a health baseline with your doctor.

Mark October 15 – December 7 on your calendar: this is the Annual Election Period (AEP) when you can switch Medicare Advantage or Part D plans. Even if you're happy with your current plan, it's worth a quick review each year since plan formularies, premiums, and networks change annually.

Free Consultation

Have Questions About Your Situation?

Every Medicare situation is different. Our Wyoming and Utah advisors provide free, personalized guidance — no pressure, no obligation.

(435) 538-3474