Turning 65 can seem daunting for a lot of people.
Medicare Parts A, B, C, D…Plans G, N, HDG…it all sounds like a bunch of alphabet soup.
On top of that, they want you to understand things like Medicare Supplement vs. Medicare Advantage, and other confusing acronyms like IEP, AEP, LEP, and more.
The worst part? If you get this wrong, you could find yourself stuck with Medicare penalties that you have to pay for as long as you have Medicare.
That’s why we’ve created a simple checklist to help you transition into Medicare as smoothly as possible.
We’ve divided this checklist into what you need to do six, three, and one month before turning 65. We’ve also included some considerations for Social Security.
If you follow this checklist, you should be able to find the right Medicare plan for you and avoid the penalties.
The Planning Stage (What to do 6 Months Before Turning 65)
Enrolling in Medicare is not mandatory.
However, if you enroll at the wrong time, you may incur permanent penalties on your Medicare premiums.
That’s why six months before turning 65, we recommend researching what Medicare covers, learning about Medicare late enrollment penalties, and finding out if you can delay enrollment past 65 without getting penalized.
Also, study the differences between Medicare Supplement and Medicare Advantage plans, and, if you plan to enroll in Medicare at 65, have an idea which plan you’re going to enroll in.
#1: Know What Original Medicare Covers
Original Medicare is split into two parts:
- Medicare Part A, which covers you inpatient hospital costs, and
- Medicare Part B, which covers your outpatient and medical costs.
Medicare Part A has a $0 premium for most people. As long as you work and pay Medicare tax for 40 quarters (10 years), you shouldn’t have to pay a premium for Medicare Part A.
Medicare Part B has a premium for most people. In 2026, the base premium for Medicare Part B is set to $202.90/month. People on higher income brackets typically pay surcharges for Medicare Part B (Medicare IRMAA).
Aside from premiums, Medicare Part A also has a deductible and copays that you’re responsible for paying when you use the plan.
| Medicare Part A Costs 2025 | |
| Deductible | $1,736 per benefit period |
| Inpatient hospital copays | Days 1-60: $0 after you pay your Part A deductible Days 61-90: $434 each day Days 91-150: $868 each day while using your 60 lifetime reserve days After day 150: You pay all costs |
| Skilled nursing facility copays | Days 1-20: $0 Days 21-100: $217 each day Days 101 and beyond: You pay all costs. |
| Home health care | $0 for covered home health care services. 20% of the Medicare-approved amount for durable medical equipment (like wheelchairs, walkers, hospital beds, and other equipment) |
| Hospice care | $0 for covered hospice care services You may also pay: A copayment of up to $5 for each prescription drug and other similar products for pain relief and symptom control while you’re at home 5% of the Medicare-approved amount for inpatient respite care. |
Meanwhile, Medicare Part B also has a deductible, and generally requires you to pay 20% of the cost for most covered services.
| Medicare Part B Costs 2025* | |
| Deductible | $283 per year |
| General cost of covered services | 20% coinsurance |
| General cost of preventative services | $0 |
*exact costs depend on the type of service you are getting. Visit Medicare.gov to find a list of covered services
#2: Find Out When To Enroll
Most people enroll in Medicare during their Initial Enrollment Period (IEP). This is a seven-month period that starts three months before the month you turn 65, runs through the month you turn 65, and ends three months after the month you turn 65.
Note: If your birthday is on the first day of the month, your IEP starts four months before the month you turn 65, runs through your birth month, and ends two months after the month you turn 65.
If you delay enrolling past your IEP, you may incur late enrollment penalties.
The late enrollment penalty for Medicare Part B is an extra 10% added to your premium for every year you delay.
However, if you have health insurance from elsewhere (such as an employer-sponsored plan), you may be able to delay enrolling in Medicare without incurring penalties.
In Medicare’s rules, if you’re on an employer-sponsored plan, and your employer has 20 or more employees, you can delay enrolling in Medicare past 65 without incurring penalties. In this situation, you’ll get a Special Enrollment Period once you leave your company, or your health coverage ends.
However, if your employer has less than 20 employees, you may need to enroll in Medicare during your IEP to avoid penalties.
For more on how Medicare interacts with different types of insurance, visit Medicare’s website.
#3: Compare Your Current Coverage to Medicare
Most people don’t enroll in Medicare Part B if they choose to stay on their employer-sponsored plan. This is because Medicare and employer-sponsored plans typically don’t coordinate benefits well. Medicare Part B also has a premium, so you can essentially end up paying for two plans while only using one.
That’s why if you’re eligible to delay enrolling in Medicare past your IEP, you should compare your current coverage to Medicare first.
Some things to compare include:
- Premiums
- Cost for using the plan (deductibles, copays, coinsurance, and maximum out-of-pocket limits)
- Networks of doctors and hospitals, and
- Drug coverage
Keep in mind that Medicare does not cover dependents. If your current plan covers your spouse or children, make sure to consider this while comparing your plan with Medicare.
People who choose to stay on their current health insurance sometimes decide to enroll in Medicare Part A only. Medicare Part A doesn’t have a premium for most people, so even though it usually doesn’t coordinate benefits well with other health insurance, there’s no extra cost for having Medicare Part A.
However, if you’re contributing to a Health Savings Account (HSA), keep in mind that any contributions you make to the account while on Medicare may be subject to tax penalties. So if you’re enrolling in Medicare, even if it’s just Medicare Part A, you may want to avoid contributing to your HSA.
#4: Research Medicare Supplement vs Medicare Advantage
If you’re planning to enroll in Medicare, you should also research your additional coverage options.
Remember, you’re responsible for paying 20% of the cost of most Medicare covered services, and there’s no limit to how expensive your out-of-pocket expenses can get. That’s why most people also enroll in additional coverage.
The two most common types of additional coverage are Medicare Supplement and Medicare Advantage Plans.
Both of these options are provided by private insurance companies. To enroll in either one of these, you must be enrolled in both Medicare Parts A and B. Aside from those, there are many differences between these plans:
| Medicare Advantage Plans | Medicare Supplement Plans | |
| Covers | Everything in Original Medicare (Part A and B) Prescription drug coverage (most plans) Dental, vision, and hearing care (some plans) Other perks | Most of the out-of-pocket expenses in Original Medicare (Part A and B) |
| Plan Options | HMO PPO PFFS SNP MSA | 10 standardized plans: Medigap Plan A, B, C, D, F, G, K, L, M, and N |
| Cost | $0 – $200+/month (Average $18.5/month according to the KFF) Deductibles and copays (varies by plan) Maximum out-of-pocket (varies by plan) | Depends on plan type, location, age, and other factors Plan G: roughly $150 – $350/month* Plan N: roughly $90 – 290/month* |
| Doctors and Hospitals | Typically has networks of local doctors and hospitals May require referrals or prior authorizations for special treatment | Any doctor or hospital that accepts Medicare Typically doesn’t require referrals or prior authorizations |
| Annual Changes | Plans typically change terms every year | Coverage usually doesn’t change, but prices may increase every year |
| Enrollment Periods | Initial Enrollment Period (IEP) Annual Election Period (AEP) Medicare Advantage Open Enrollment Period (MA OEP) Special Enrollment Periods (SEPs) No medical underwriting required typically | Medigap Open Enrollment Period (OEP) Special Enrollment Periods (SEPs) May require medical underwriting if you enroll outside your Medigap OEP or a SEP |
*These are rough estimates. Price range varies by age, location, and other factors. To find accurate price ranges, chat with a licensed insurance agent at no cost to you.
Medicare Supplement Plans work as secondary insurance to Original Medicare. They help cover your out-of-pocket expenses with Medicare.
There are currently 10 standardized Medicare Supplement Plans, namely Medicare Supplement Plan A, B, C, D, F, G, K, L, M, and N. Each plan letter provides varying levels of coverage.
Because it’s secondary insurance to Original Medicare, Medicare Supplement Plans will cover you for any doctor or hospital that takes Medicare. You typically do not need to request prior authorization from your insurance company with a Medicare Supplement Plan.
However, this also means that Medicare Supplement Plans typically do not cover services that Original Medicare doesn’t cover. Since Original Medicare does not cover most prescription drugs at pharmacies, you may also need to enroll in a standalone Medicare Part D prescription drug plan if you choose Medicare Supplement and want more drug coverage.
One of the main complaints for Medicare Supplement Plans is that its premiums can be expensive for many people. The exact premiums depend on the plan type, the insurance company, your age, your location, and a few other factors.
For instance, a typical Medicare Supplement Plan G can cost anywhere from $150-350/month for a 65 year old. Some states have lower average premiums, while others have higher average premiums.
Medicare Advantage Plans work by replacing Original Medicare. If you sign up for a Medicare Advantage Plans, Medicare essentially transfers responsibility of your healthcare over to your Medicare Advantage Plan.
Medicare Advantage Plans are required to provide the same coverage as Original Medicare. However, they are also free to include other services and benefits not included with Original Medicare.
Most Medicare Advantage Plans have a built-in prescription drug plan, while many Medicare Advantage Plans include benefits for routine dental care, eyeglasses, and hearing aids (three things which Original Medicare typically doesn’t cover).
Medicare Advantage Plans usually have networks of local doctors and hospitals that they work with to provide beneficiaries with low-cost healthcare. If you get services outside your plan’s network, you may not be covered, or may have to pay higher copays, unless it’s an emergency.
Many Medicare Advantage Plans have low to $0 premiums. This is because when you enroll in a Medicare Advantage Plan, Original Medicare pays a fixed amount to the plan for your healthcare. That’s why many Medicare Advantage Plans can offer $0 premiums.
#5: Decide Which Plan to Enroll In
Once you know all the differences between Medicare Supplement and Medicare Advantage, you’re ready to look for actual plans available in your area.
Some things to consider are:
- Premiums vs copays – Generally speaking, plans with higher premiums tend to have lower copays, while plans with lower premiums tend to have higher copays or more restrictions. While there are plenty exceptions, this is generally how insurance works. So look at the plan options in your area and calculate what makes the most sense for you.
- Networks – Both Medicare Advantage Plans and Medicare Part D prescription drug plans have networks of doctors, hospitals, and pharmacies that they work with. Be sure to review these networks before enrolling to prevent unwanted surprises. Some people choose plans that have their preferred doctor in-network, while others choose plans that have many doctors and hospitals in-network close to where they live.
- Prescription drug coverage – Medicare Part D prescription drug plans are almost completely free to choose which drugs they cover and which ones they don’t. While choosing a plan, look for one that includes your prescription drugs in its formulary.
You can find the plans available in your area you can contact a licensed insurance agent for help comparing your options at no cost to you.
However, look out for pitfalls here — some plans don’t tell you clearly whether they cover your doctors or your drugs. So if you’d like a second opinion to make sure you don’t make a mistake, you can always call our team of licensed insurance agents at no cost to you.
The Signing Up Stage (What to do 3 Months Before Turning 65)
If you’ve decided you want Medicare, three months before you turn 65 is usually the time to:
- Enroll in Medicare Parts A and B
- Enroll in a Medicare Supplement or Medicare Advantage Plan
- Enroll in a Medicare Part D prescription drug plan
You generally want to enroll as early as possible. If you enroll before your 65th birth month, your coverage will usually begin on the first day of your 65th birth month.
However, if you enroll during or after your 65th birth month, your coverage will usually begin one month after you enroll — leaving you without full coverage until that time.
Also, remember that if you enroll past your Initial Enrollment Period, you may be subject to permanent penalties for your Medicare Part B premiums (10% added for every year you delay).
#1: Enroll in Medicare Parts A and B
If you’re already taking Social Security or Railroad Retirement Board benefits, you’ll automatically be enrolled in Medicare.
If you’re not yet taking Social Security or Railroad Retirement Board benefits, the easiest way to enroll in Medicare Parts A and B is to sign up on Social Security’s website. You’ll provide:
- Your Social Security number
- Where you were born (city, state, country)
- Start and end dates for any current group health plans
- Start and end dates for any group health plans after age 65
Alternatively, you can call Social Security at +1 800-772-1213 to enroll, or visit your local Social Security Office.
Medicare usually takes a couple of days to approve your application and assign you a Medicare number. You should also receive your Medicare card and “Welcome to Medicare” packet about two weeks after you apply.
#2: Enroll in a Medicare Supplement or Medicare Advantage Plan
Once you have your Medicare number, you can enroll in any Medicare Supplement or Medicare Advantage Plan in your area.
Simply contact the plan you want to enroll in, provide any details they ask for, and your coverage should begin on the same date as your Medicare coverage. If you’re working with an agent, they should help you with this process.
Generally speaking, you’ll want to enroll in a Medicare Supplement or Medicare Advantage as soon as you can for a couple of reasons:
Medicare Supplement – If you enroll in a Medicare Supplement Plan within six months of your Medicare Part B start date, the plan must take you in regardless of your health condition. This window is known as the Medigap Open Enrollment Period.
If you want to enroll in a Medicare Supplement Plan outside your Medigap Open Enrollment Period, most plans will require you to medically qualify to join. They typically ask you 30-or-so health questions, and have the right to decline your application, or charge you higher rates, depending on your answers.
Medicare Advantage – If you don’t enroll in a Medicare Advantage Plan during your Initial Enrollment Period, you may have to wait for the next Annual Enrollment Period before you can join — leaving you susceptible to high out-of-pocket costs with Original Medicare only.
Unlike Medicare Supplement Plans, where you can enroll any time of the year, there are only certain periods when you can join a Medicare Advantage Plan.
The main time to join a Medicare Advantage Plan after your IEP is the Annual Enrollment Period (AEP), which runs from October 15 to December 7 every year.
#3: Enroll in a Medicare Part D Prescription Drug Plan
If you enroll in a Medicare Advantage Plan with a built-in prescription drug coverage (MAPD), then you won’t need to enroll in Medicare Part D separately.
If you’re not enrolling in a MAPD, you can enroll in a standalone Medicare Part D plan (PDP) during your Initial Enrollment Period.
Like Medicare Advantage Plans, you can only enroll in Medicare Part D during certain times of the year. The main time to enroll in Medicare Part D after your IEP is the Annual Enrollment Period (AEP), which runs from October 15 to December 7 every year.
If you don’t enroll in a Medicare Part D plan and you also don’t have creditable coverage from elsewhere, you’ll get a late enrollment penalty. “Creditable coverage” simply means a drug plan that’s equal to or better than Medicare Part D (you can ask your current drug plan if it is considered creditable for Medicare).
The penalty is 1% of the national base Part D premium for every month that you delay. In 2025, the national base Part D premium is set to $38.99.
The Preparation Stage (What to do 1 Month Before Turning 65)
One month before turning 65, if you’ve been following this guide, you should have everything in place to transition to Medicare.
You should already have your:
- Red, White, and Blue Medicare Card
- Medicare Supplement or Medicare Advantage Card, and
- Medicare Part D card (if not enrolling in Medicare Advantage)
You should also contact any health insurance you have and inform them you’re switching to Medicare. If you’re going to leave your current plan, one month before turning 65 can be a good time to do it.
Now, during the Preparation Stage, make sure everything is in order.
If you weren’t able to plan six months before turning 65, or sign up three months before, don’t panic. You can still do these things.
However, you may want to do them as early as possible to avoid mistakes and have room for any possible delays.
Social Security Decisions at 65
Aside from Medicare, you also may want to consider when you plan to start taking your Social Security Benefits.
Here’s what to know:
Find Your Full Retirement Age (FRA)
Your Full Retirement Age (FRA) is the age at which you can start claiming your full Social Security benefit.
Your FRA depends on when you were born:
| Birth Year | Full Retirement Age (FRA) |
| 1943 – 1954 | 66 |
| 1955 | 66 and 2 months |
| 1956 | 66 and 4 months |
| 1957 | 66 and 6 months |
| 1958 | 66 and 8 months |
| 1959 | 66 and 10 months |
| 1960 and later | 67 |
Learn How Enrolling Early Affects Your SS Benefit
You can start taking your Social Security benefits as early as age 62. However, if you start taking before your FRA, you’ll receive a reduced amount. Here’s a chart from Social Security showing your reduction amounts:
| Year of Birth 1. | Full (normal) Retirement Age | Months between age 62 and full retirement age 2. | At Age 62 3. | |||
| A $1000 retirement benefit would be reduced to | The retirement benefit is reduced by 4. | A $500 spouse’s benefit would be reduced to | The spouse’s benefit is reduced by 5. | |||
| 1943-1954 | 66 | 48 | $750 | 25.00% | $350 | 30.00% |
| 1955 | 66 and 2 months | 50 | $741 | 25.83% | $345 | 30.83% |
| 1956 | 66 and 4 months | 52 | $733 | 26.67% | $341 | 31.67% |
| 1957 | 66 and 6 months | 54 | $725 | 27.50% | $337 | 32.50% |
| 1958 | 66 and 8 months | 56 | $716 | 28.33% | $333 | 33.33% |
| 1959 | 66 and 10 months | 58 | $708 | 29.17% | $329 | 34.17% |
| 1960 and later | 67 | 60 | $700 | 30.00% | $325 | 35.00% |
Note: You may see a small increase or decrease for inflation, but your benefit will not increase based on your age.
If you choose to delay taking Social Security past your FRA, you’ll get an increased benefit. Your benefit will increase by 8% for every year that you delay past your FRA up to age 70.
Because of this, the most common times for people to start taking Social Security are at age 62, their FRA, or age 70.
Taking it earlier allows you to enjoy your benefits for a longer time. However, taking it later allows you to enjoy a bigger benefit.
Calculate Your Break Even Points
To help you decide when you should start taking Social Security, you can calculate the break even points.
To help you determine your breakeven point, you can use this simple formula:
Total additional benefits received by taking early / Monthly benefit difference
= Break-even point
For example, let’s say you want to find out the break-even point if you start taking at your FRA of 67 versus age 70.
First, find the monthly benefit for each of these ages. Let’s say your monthly benefit for taking at age 67 is $1,900, and your monthly benefit for taking at age 70 is $2,400 (rounded).
Your total additional benefits received by taking early would be $1,900 x 24 months = $45,600. And your monthly benefit difference would be $500 ($2,400 – $1,900 = $500).
45,600 / 500
= 91 (rounded)
This means that your breakeven point for taking at 70 would be 91 months, or roughly 7.5 years.
You can use this formula to calculate your break even points depending on which age you decide to start taking Medicare.
Check How Your Income Affects Your Social Security Benefit
If you are still working, your income will also affect how much you can take from Social Security.
In 2025, any income you make above $23,400 will be subject to the Low Earnings Test. For every $2 that you make above this limit, $1 will be withheld from your Social Security benefit.
Meanwhile, any income you make above $61,160 will be subject to the High Earnings Test. For every $3 that you make above this limit, $1 will be withheld from your Social Security benefit.
However, these limits no longer apply once you reach your Full Retirement Age (FRA).
Decide When to Take Social Security
Not everyone is concerned about breakeven points and maximizing their benefit. Some people simply want to start taking it as early as possible. Meanwhile, other people carefully go through the math, consider their health and try to estimate when they may pass, and use these numbers to get as much from Social Security as they can.
Whatever the case, the decision is completely up to you. So take a look at the numbers, and determine whether you want benefits now, or if you want to wait for a bigger check.
Grab The Turning 65 Checklist
As you approach age 65, learning about Medicare and Social Security can seem daunting.
But if you follow the checklist above, you should be able to enroll in a Medicare plan that’s right for you without worrying about penalties.
To make things easier for you, we created a simple, easy-to-follow, and printable checklist for turning 65.
You can grab it by clicking the button below.