Let's set the stage
The month you turn 65 is a deadline, not a suggestion. Most of the expensive Medicare mistakes we see in our Draper office came from someone doing the right things in the wrong order: buying a drug plan before Part B was confirmed, dropping job coverage before Medicare started, or letting the Medigap window close. This checklist puts the steps in order. Print it, and check them off.
6 months before you turn 65
- Log in to your my Social Security account. Confirm you or your spouse have 40 quarters of work, which means premium-free Part A. See Medicare eligibility.
- Talk to your employer's benefits office if you are still working. Ask in writing: how many employees does the company have, and does the group plan pay first or does Medicare? With 20 or more employees, the group plan generally pays first and you may be able to delay Part B.
- Check your HSA. Once any part of Medicare starts, you cannot contribute to a Health Savings Account. Medicare.gov advises stopping HSA contributions 6 months before you retire and sign up to avoid a tax penalty, because premium-free Part A coverage can start up to 6 months before the date you apply.
- List your doctors and prescriptions. You will need both to compare plans.
3 months before your birthday month (your Initial Enrollment Period opens)
- Sign up for Part A and Part B at ssa.gov unless you are being enrolled automatically. Signing up now means coverage starts the first of the month you turn 65.
- If you are delaying Part B because of current employer coverage, you can still take premium-free Part A, unless you want to keep contributing to an HSA.
- Watch your mail for your Medicare card.
2 months before
- Choose your path. Original Medicare with a Medigap plan and a Part D plan, or a Medicare Advantage plan. Our enrollment guide has a side by side table.
- Compare plans by county. For 2027, the CMS landscape file shows 28 non special needs Medicare Advantage plans in Salt Lake, Utah and Davis counties, 24 in Weber, and as few as 6 in counties such as Carbon, Sanpete, Sevier and Uintah. There are 8 stand-alone Part D plans statewide.
- Check your doctors in each network and run your drug list against each plan's formulary.
1 month before
- Apply for your plan so it starts the same day as Part B.
- If you chose Medigap, apply now. Your 6-month Medigap open enrollment begins the first month you have Part B and are 65 or older, and many carriers let you apply ahead of that date.
- Do not cancel employer or individual coverage until you have your Medicare start dates in writing.
- If you have Marketplace coverage, plan to end it so it stops when Medicare starts. Once you are eligible for premium-free Part A, you generally can no longer get premium tax credits for a Marketplace plan.
The month you turn 65
- Confirm your Medicare card, plan card and start dates all match.
- Book your "Welcome to Medicare" preventive visit. Part B covers it once, within the first 12 months you have Part B.
- Fill a prescription with your new drug plan to make sure it processes.
After 65: keep these dates on the calendar
| When | What |
|---|---|
| Late September each year | Read your plan's Annual Notice of Change |
| October 15 to December 7 | Open Enrollment: change Medicare Advantage or Part D plans |
| January 1 to March 31 | Medicare Advantage Open Enrollment, if you are in an MA plan |
| Within 8 months of leaving a job | Sign up for Part B with your Special Enrollment Period, if you delayed it |
| Every 12 months | Yearly wellness visit under Part B |
Mistakes to avoid
- Relying on COBRA or retiree coverage to delay Part B. Neither counts as current employment coverage. A Part B penalty is 10% for each full 12 months you were late, usually for life.
- Going without drug coverage. Going 63 days or more without creditable drug coverage after your IEP triggers a Part D penalty. See late enrollment penalties.
- Missing the Medigap window. After it closes, carriers can ask health questions.
- Choosing a plan on the TV ad. Pick the plan that fits your doctors and drugs. That is the right plan for you, whatever the ad says.
Documents to gather
| Document | Why you need it |
|---|---|
| Social Security number and a my Social Security account | To apply for Parts A and B online at ssa.gov |
| Employer or union coverage details, with end date if leaving | To decide about delaying Part B, and for form CMS-L564 |
| Creditable drug coverage notice from your current plan | Proof that protects you from the Part D penalty |
| A list of every prescription with dose and how often | To compare Part D or Medicare Advantage drug costs |
| Your doctors, specialists and preferred hospital | To check plan networks |
| Your current Marketplace plan details, if any | So you can cancel it once Medicare starts |
Questions to ask your HR department in writing
- How many employees does the company have? If fewer than 20, Medicare usually pays first and you likely need Part B.
- Is our drug coverage creditable for Medicare Part D?
- Does the plan require me to enroll in Part A or Part B at 65?
- Will you complete form CMS-L564 when I leave?
- If I keep contributing to an HSA, when should I stop before Medicare starts?
Two Utah examples
These are illustrative, not real clients.
Retired in Sandy, no job coverage. Robert turns 65 in August. He signs up for Parts A and B in May so coverage starts August 1. Salt Lake County has 28 Medicare Advantage plans for 2027, 15 with a $0 plan premium, and every Utah county can use the 8 stand-alone Part D plans. He compares a Medigap plan plus Part D against Medicare Advantage using his drug list, chooses one, and applies in June so it starts August 1 too.
Still working in Lehi at a large employer. Maria turns 65 but stays on her employer's group plan, which has more than 20 employees and creditable drug coverage. She takes premium-free Part A only if she is not contributing to an HSA, delays Part B, and keeps the creditable coverage letter. When she retires, she has 8 months to sign up for Part B with no penalty, and her 6 month Medigap open enrollment starts when Part B begins.
If your birthday is on the first of the month
Medicare treats you as turning 65 the month before. Someone born on July 1 has a birthday month of June for Medicare purposes, so the Initial Enrollment Period opens in March and premium-free Part A can start June 1. Put the earlier date on your calendar so you do not start the checklist a month late.
We can walk the list with you
Call 801-255-5340, Monday through Friday, 9:30am to 5pm Mountain, or visit our office at 61 W 13490 S, Suite 201, in Draper. Bring this checklist and your medication list.
Everything Senior Insurance is a licensed insurance agency in Utah. We are not connected with or endorsed by the U.S. government or the federal Medicare program.
Frequently asked questions
How early should I start planning for Medicare before I turn 65?
About six months ahead. That gives time to check work credits, talk to your employer, stop HSA contributions if needed, and sign up in the first three months of your Initial Enrollment Period.
Should I stop contributing to my HSA before Medicare?
Yes. You cannot contribute to an HSA once any part of Medicare starts. Medicare.gov advises you and your employer to stop HSA contributions 6 months before you retire and sign up, to avoid a tax penalty.
Do I need Part B if I am still working at 65?
Not always. If you have coverage from current employment at a company with 20 or more employees, you can often delay Part B without penalty. Confirm with the employer in writing.
When should I apply for a Medigap plan?
During your 6-month Medigap open enrollment, which starts the first month you have Part B and are 65 or older. Applying a month or so before Part B starts helps your coverage begin on the same day.
Sources
- Medicare.gov: When can I sign up for Medicare?
- Medicare.gov: When does Medicare coverage start?
- Medicare.gov: Working past 65
- Medicare.gov: Avoid late enrollment penalties
- Medicare.gov: Preventive and screening services
- HealthCare.gov: Changing from the Marketplace to Medicare
- Social Security: Sign up for Medicare
- CMS: Prescription drug coverage (Landscape source files)
Updated October 26, 2026 by the Everything Senior Insurance Data Desk.