How to Enroll in Medicare: Your Must-Do Guide Before Turning 65 in 2026

Turning 65 is a significant milestone, especially when it comes to your health insurance options. If you’re new to Medicare, understanding the enrollment windows is critically important—missing them can result in lifelong penalties and gaps in your coverage. Specifically, the process should begin well before your birthday month, with certain steps starting as early as six months in advance.

This guide breaks down exactly what you need to do—and when—to ensure a smooth transition to Medicare. From creating your Social Security account to choosing between Original Medicare and Medicare Advantage plans, we’ll walk through each step in the months leading up to your 65th birthday. By following this timeline, you’ll be well-prepared when your Initial Enrollment Period arrives and can make informed decisions about your healthcare coverage.

6 Months Before Turning 65: Start Learning the Basics

Six months before your 65th birthday marks the ideal time to begin learning about Medicare. Starting early gives you ample time to understand the program’s structure and make informed decisions about your healthcare coverage.

Understand what Medicare is and who qualifies

Medicare is a federal health insurance program primarily designed for people 65 or older ^[1]. Additionally, those under 65 with certain disabilities, End-Stage Renal Disease (permanent kidney failure requiring dialysis or transplant), or ALS (Lou Gehrig’s disease) may qualify ^[2].

To be eligible for Medicare at age 65, you must be a United States citizen or a legal resident who has lived in the country for at least five consecutive years ^[1]. Most people automatically qualify for premium-free Part A coverage if they or their spouse worked for at least 10 years (40 quarters) in Medicare-covered employment and paid Medicare taxes during that time ^[1].

Learn about Parts A, B, C, and D

Medicare consists of four distinct parts, each covering different aspects of healthcare:

• Part A (Hospital Insurance): Covers inpatient hospital care, skilled nursing facility care, hospice care, and some home health services ^[3]. Most people don’t pay a premium for Part A if they’ve paid Medicare taxes while working ^[1].
• Part B (Medical Insurance): Covers outpatient care including doctor visits, preventive services, medical equipment, lab tests, and some home health care ^[3]. Everyone pays a monthly premium for Part B, which was $174.70 in 2024 for most people ^[4].
• Part C (Medicare Advantage): Offered by private insurance companies approved by Medicare, these plans bundle Parts A and B coverage and often include prescription drug coverage and additional benefits ^[3].
• Part D (Prescription Drug Coverage): Helps cover prescription medication costs ^[3]. You can get this coverage by joining a Medicare drug plan or through many Medicare Advantage plans ^[4].

Furthermore, Medigap (Medicare Supplement Insurance) policies are available to help cover out-of-pocket costs like deductibles and coinsurance in Original Medicare ^[3].

Know the difference between Original Medicare and Advantage plans

Understanding the distinction between Original Medicare and Medicare Advantage is crucial for making the right choice:

Original Medicare is administered directly by the federal government and includes Parts A and B ^[5]. With this option, you can visit any doctor or hospital that accepts Medicare nationwide ^[6]. Nevertheless, Original Medicare typically covers about 80% of approved costs, leaving you responsible for the remaining 20% with no annual limit on out-of-pocket expenses ^[6]. To help with these costs, you can purchase a separate Medigap policy ^[6].

Medicare Advantage (Part C) plans are offered by private insurance companies that contract with Medicare ^[7]. These plans must cover everything Original Medicare does, plus they often include prescription drug coverage and extra benefits like dental, vision, and hearing care ^[7]. Although Medicare Advantage plans typically limit you to in-network providers and may require referrals for specialists, they do offer an annual cap on out-of-pocket expenses ^[6].

Consequently, your choice between these options depends on factors like your budget, health needs, preferred doctors, and desire for additional benefits. Take time during this early stage to thoroughly review both options so you’ll be prepared to make an informed decision as your enrollment period approaches.

5 Months Before: Get Help and Set Up Accounts

Now that you understand Medicare basics, it’s time to set up important accounts and seek guidance. With five months remaining until your 65th birthday, focus on creating necessary online accounts and connecting with experts who can provide personalized help.

Create your Social Security account

Setting up your personal my Social Security online account is a crucial step that makes your transition to Medicare significantly easier. This free and secure account lets you request a replacement Social Security card, check application status, estimate future benefits, or manage existing benefits ^[8].

To create your account:

• Visit www.ssa.gov/myaccount
• Choose whether to create a Login.gov or ID.me account
• Follow the prompts to verify your identity

Once established, your account provides numerous benefits depending on your situation. If you’re not yet receiving benefits, you can get personalized retirement estimates, check application status, and access your Social Security Statement. For those already receiving benefits, you can set up direct deposit, access tax forms, and print benefit verification letters ^[8].

Need help? Call 1-800-772-1213 and ask for “Help Desk” for priority service between 8:00 a.m. and 7:00 p.m. local time, Monday through Friday ^[8].

Talk to SHIP or a licensed Medicare advisor

The State Health Insurance Assistance Program (SHIP) offers invaluable free, objective, one-on-one counseling to help you navigate Medicare decisions. Established by Congress in 1990, SHIP assists up to 4 million beneficiaries annually ^[9].

SHIP counselors are highly trained and certified to help you with:

• Choosing between Original Medicare and Medicare Advantage
• Understanding Medicare Prescription Drug Coverage (Part D)
• Applying for programs that help pay for healthcare costs
• Comparing Medicare Supplement (Medigap) options ^[10]

SHIP services are available through in-person meetings, phone calls, online consultations, or email. All services are completely free regardless of your income level ^[9]. To connect with your local SHIP office, visit shiphelp.org.

Apart from SHIP, you might consider working with a licensed Medicare advisor. You can find advisors by searching online, contacting companies that sell Medicare plans, or reaching out to professional agent associations in your state ^[11].

Check with your employer if you’re still working

If you plan to continue working past 65, it’s essential to understand how your employer’s health coverage will coordinate with Medicare. First, ask your human resources representative whether your employer requires you to take Medicare Parts A and B ^[12].

For employees at companies with 20 or more workers, group health plans must offer the same benefits to employees over 65 as they do to younger workers ^[13]. In these cases, your employer plan typically pays first, with Medicare serving as secondary coverage.

However, coordination rules differ based on your employer’s size and whether you’re actively employed or retired. Therefore, speak with your benefits administrator or employer’s human resources department to learn exactly how your benefits will work with Medicare ^[14].

Your employer may ask for your name, date of birth, gender, and Medicare Number to update Medicare about your other insurance. Providing this information helps ensure your claims are paid correctly ^[15].

4 Months Before: Explore Your Coverage Options

With four months remaining until your 65th birthday, it’s time to compare specific Medicare coverage options. At this stage, you’ve learned the basics and set up your accounts—now you need to make concrete decisions about your healthcare coverage.

Decide between Original Medicare and Medicare Advantage

The most fundamental Medicare decision involves choosing between Original Medicare and Medicare Advantage. Both options have distinct characteristics that may appeal to different needs:

Original Medicare:

• Allows you to see any doctor or hospital that accepts Medicare nationwide ^[16]
• Typically covers 80% of approved costs, leaving you responsible for 20% with no yearly limit on out-of-pocket expenses ^[16]
• Requires separate enrollment in a prescription drug plan if you want medication coverage ^[17]
• Offers the flexibility to purchase a Medigap policy to help with out-of-pocket costs ^[18]

Medicare Advantage:

• Offered by private insurance companies that must cover everything Original Medicare does ^[18]
• Often includes prescription drug coverage and extra benefits like vision, dental, and hearing care ^[18]
• May limit you to in-network providers and require referrals for specialists ^[16]
• Includes an annual cap on out-of-pocket expenses ^[19]

In 2025, nearly 9 in 10 Medicare Advantage plans included prescription coverage ^[17], making them attractive to many beneficiaries seeking all-in-one coverage.

Consider if you need Part D for prescriptions

Prescription drug coverage is not automatically included with Original Medicare. Part D helps pay for both brand-name and generic medications ^[20] and can be obtained in two ways:

1. Adding a separate Medicare drug plan (PDP) to Original Medicare ^[1]
2. Enrolling in a Medicare Advantage plan that includes prescription coverage ^[1]

Most Medicare drug plans organize medications into “tiers” with different cost levels ^[2]. Generally, drugs in lower tiers cost less than those in higher tiers.

Even if you don’t currently take prescription drugs, consider enrolling in Part D when first eligible to avoid potential late enrollment penalties later ^[1].

Look into Medigap for extra coverage

Medicare Supplement Insurance (Medigap) helps fill the “gaps” in Original Medicare coverage by paying some of the costs that Original Medicare doesn’t cover ^[21]. Important facts about Medigap include:

• You must have Medicare Parts A and B to purchase a Medigap policy ^[21]
• Insurance companies can only sell standardized Medigap policies that follow federal and state laws ^[21]
• There are ten standardized plans (lettered A-N) with different levels of coverage ^[22]
• Plan F and Plan G are the most popular options, with Plan F covering all gaps in Medicare ^[22]
• If you join a Medicare Advantage plan, you cannot use a Medigap policy ^[1]

Comparing plans is essential since costs can vary considerably between insurance companies, even though the standardized benefits remain the same ^[22].

By thoroughly exploring these options four months before turning 65, you’ll be better prepared to make informed decisions when your Initial Enrollment Period begins. Remember that your choices now will significantly impact both your healthcare access and out-of-pocket costs for years to come.

3 Months Before: Enroll in Medicare

Three months before turning 65 marks the start of your Medicare Initial Enrollment Period—a crucial window for taking action. At this stage, you’ve learned about Medicare options and now it’s time to officially sign up for coverage.

Understand your Initial Enrollment Period (IEP)

Your Initial Enrollment Period spans seven months total: three months before your birth month, your birth month itself, and three months after ^[3]. This timing is critical because missing your IEP can result in permanent late enrollment penalties and coverage gaps ^[23].

For most people born on the 2nd through the 31st of the month, the IEP works as described above. In contrast, if your birthday falls on the 1st of the month, your IEP shifts—it begins and ends one month earlier ^[3]. For instance, if you turn 65 on June 1, 2026, your enrollment window runs from February 1 through August 31, 2026 ^[3].

The timing of your enrollment also affects when your coverage begins:

• If you enroll before your 65th birthday month: Coverage starts the first day of your birthday month ^[24]
• If you enroll during your birthday month or the three months after: Coverage starts the following month ^[24]

Enroll in Parts A and B through SSA.gov

Unless you’re automatically enrolled (see below), you must take action to sign up for Medicare. There are three primary ways to enroll ^[6]:

1. Online at www.SocialSecurity.gov (fastest method)
2. By phone at 1-800-772-1213 (TTY: 1-800-325-0778), Monday through Friday, 7 a.m. to 7 p.m. ^[7]
3. In person at your local Social Security office ^[6]

After enrollment, you should receive your Medicare card in approximately three weeks ^[6].

Check if you’re automatically enrolled

Certainly, some people don’t need to take any enrollment action. You’ll be automatically enrolled in Medicare Parts A and B if:

• You receive Social Security or Railroad Retirement Board benefits at least four months before turning 65 ^[5]
• You’ve received disability benefits for 24 months ^[6]
• You have ALS (Lou Gehrig’s disease) and start receiving disability ^[6]

Even with automatic enrollment, you’ll need to decide about additional coverage like Medicare Advantage, Part D prescription plans, or Medigap ^[25].

Remember that missing your Initial Enrollment Period can result in lifetime penalties—10% added to your Part B premium for each 12-month period you could have enrolled but didn’t ^[23].

After Enrollment: Review and Prepare for Next Steps

After successfully enrolling in Medicare, your journey isn’t complete. Several important steps remain to optimize your coverage and prepare for future changes.

Compare Medicare Advantage or Medigap plans

Once enrolled in Original Medicare, consider additional coverage options. Medicare.gov/plan-compare offers tools to compare plans side by side ^[26]. For Medicare Advantage, examine different plan types—HMO, PPO, PFFS, SNP, or MSA—each with varying provider networks and drug coverage ^[27].

When considering Medigap, remember you have a six-month Open Enrollment Period starting when you’re 65 and enrolled in Part B ^[28]. During this period, companies must sell you a policy regardless of health status ^[28]. The benefits in each lettered plan (A-N) are standardized, though premiums vary significantly between insurers ^[28].

Understand what’s not covered (dental, vision, hearing)

Original Medicare doesn’t cover several important services, primarily dental, vision, and hearing care ^[4]. These gaps include:

• Routine dental cleanings, fillings, and extractions ^[4]
• Eye exams for prescription glasses ^[4]
• Hearing aids and fitting exams ^[4]

Indeed, 90% of the public considers expanding Medicare to include these services a priority ^[29]. Moreover, 16% of Medicare beneficiaries reported being unable to get needed dental, vision, or hearing care, with 70% citing cost as the barrier ^[29]. Medicare Advantage plans often include some coverage for these services as additional benefits ^[30].

Plan for annual reviews during Open Enrollment

Throughout your Medicare journey, annual reviews remain essential. The Fall Open Enrollment Period (October 15-December 7) allows you to make numerous coverage changes effective January 1 ^[31]. Furthermore, if you have a Medicare Advantage plan, the Medicare Advantage Open Enrollment Period (January 1-March 31) lets you switch plans or return to Original Medicare ^[32].

Review your plan’s Annual Notice of Change letter each September to understand how costs, benefits, and provider networks might change ^[8]. Primarily, consider whether your current plan still meets your health needs, covers your preferred providers, and includes your medications ^[8].

Conclusion

Navigating Medicare enrollment represents a crucial step as you approach your 65th birthday in 2026. Starting your preparation six months before turning 65 gives you adequate time to understand the complexities of Medicare and make informed decisions about your healthcare coverage. Most importantly, adhering to the timeline outlined in this guide helps you avoid costly penalties and potential gaps in your health insurance.

Remember, your Initial Enrollment Period begins three months before your birth month and offers a limited window to secure coverage. Therefore, missing this opportunity could result in lifelong premium increases. Additionally, the choice between Original Medicare and Medicare Advantage depends largely on your specific health needs, budget considerations, and preferences regarding provider networks.

Certainly, establishing your online Social Security account early streamlines the enrollment process. Likewise, consulting with SHIP counselors or licensed Medicare advisors provides personalized guidance tailored to your situation. These professionals can help clarify confusing aspects of Medicare and assist you in selecting the most appropriate coverage.

After enrolling, your Medicare journey continues with annual reviews during Open Enrollment periods. These regular checkups ensure your coverage remains aligned with your evolving healthcare requirements. Furthermore, understanding what Medicare doesn’t cover—particularly dental, vision, and hearing services—allows you to plan accordingly for these potential expenses.

The path to Medicare might seem overwhelming at first glance. However, breaking down the process into manageable steps makes this transition significantly smoother. Following this timeline empowers you to approach your 65th birthday with confidence, knowing your healthcare needs will be properly addressed through appropriate Medicare coverage.

References

[1] – https://www.medicare.gov/publications/11109-your-guide-to-medicare-prescription-drug-coverage.pdf
[2] – https://www.humana.com/medicare/medicare-resources/what-is-medicare-part-d
[3] – https://www.uhc.com/medicare/medicare-education/medicare-initial-enrollment-period.html
[4] – https://www.medicare.gov/providers-services/original-medicare/not-covered
[5] – https://www2.unitedamerican.com/articles/september-2021/will-i-be-automatically-enrolled-in-medicare-part-a-and-b
[6] – https://www.uhc.com/medicare/medicare-education/how-to-enroll-in-medicare.html
[7] – https://www.ssa.gov/medicare/sign-up
[8] – https://www.ncoa.org/article/3-ways-to-prepare-for-medicare-open-enrollment/
[9] – https://www.kff.org/medicare/the-role-of-ships-in-helping-people-with-medicare-navigate-their-coverage/
[10] – http://acl.gov/programs/connecting-people-services/state-health-insurance-assistance-program-ship
[11] – https://www.retireguide.com/medicare/customer-service/advisors/
[12] – https://www.aetna.com/medicare/understanding-medicare/working-past-65.html
[13] – https://www.ssa.gov/pubs/EN-05-10043.pdf
[14] – https://www.medicare.gov/basics/get-started-with-medicare/medicare-basics/working-past-65
[15] – https://www.medicare.gov/publications/11546-Medicare-Coordination-of-Benefits-Getting-Started.pdf
[16] – https://www.medicare.gov/basics/get-started-with-medicare/get-more-coverage/your-coverage-options/compare-original-medicare-medicare-advantage
[17] – https://www.aarp.org/medicare/original-medicare-vs-advantage/
[18] – https://www.ncoa.org/article/original-medicare-vs-medicare-advantage-whats-the-difference/
[19] – https://www.uhc.com/news-articles/medicare-articles/medicare-coverage-gaps
[20] – https://www.medicare.gov/health-drug-plans/part-d
[21] – https://www.cms.gov/medicare/health-drug-plans/medigap
[22] – https://boomerbenefits.com/medicare-supplemental-insurance/medigap-comparison-chart/
[23] – https://www.medicare.gov/basics/costs/medicare-costs/avoid-penalties
[24] – https://www.medicare.gov/basics/get-started-with-medicare/sign-up/when-does-medicare-coverage-start
[25] – https://www.medicare.gov/basics/get-started-with-medicare/before-65
[26] – https://www.medicare.gov/plan-compare/
[27] – https://www.medicare.gov/health-drug-plans/health-plans/your-health-plan-options/compare
[28] – https://www.medicare.gov/publications/02110-medigap-guide-health-insurance.pdf
[29] – https://www.kff.org/health-costs/dental-hearing-and-vision-costs-and-coverage-among-medicare-beneficiaries-in-traditional-medicare-and-medicare-advantage/
[30] – https://www.ncoa.org/article/what-medicare-covers-for-dental-vision-and-hearing-a-guide-for-older-adults/
[31] – https://www.medicareinteractive.org/understanding-medicare/health-coverage-options/changing-medicare-coverage/how-to-switch-medicare-advantage-plans-or-switch-from-medicare-advantage-to-original-medicare
[32] – https://www.aarp.org/medicare/faq/can-i-change-part-c-plans-if-unhappy/