Medicare Enrollment Help: Your Complete Guide for 2026

Medicare enrollment doesn't have to be overwhelming. Whether you're turning 65, leaving employer coverage, or helping a parent navigate the process, this guide walks you through every step of enrolling in Medicare, including when to sign up, what your options are, and how to avoid costly mistakes.

The stakes are high: miss your enrollment window and you could face permanent penalties that increase your premiums for life. But with the right Medicare enrollment help, you can make confident decisions and get the coverage you need.

When Should You Enroll in Medicare?

The answer depends on your situation. Most people have a specific enrollment window they must use, and missing it can result in penalties or coverage gaps.

Your Initial Enrollment Period (IEP)

If you're turning 65, your Initial Enrollment Period is a 7-month window:

• 3 months before your 65th birthday month
• Your 65th birthday month
• 3 months after your 65th birthday month

Best practice: Enroll during the first 3 months of your IEP. This ensures your coverage starts the first day of your birthday month (or the first day of the prior month if your birthday is on the 1st).

When Your Coverage Starts

What If You're Still Working at 65?

If you have employer health insurance when you turn 65, you may be able to delay Medicare without penalty, but it depends on your employer's size.

The 20-Employee Rule

When you stop working or lose employer coverage, you get a Special Enrollment Period (SEP): 8 months to enroll in Medicare Part B without penalty. Don't wait until the end, as coverage won't start until the month after you enroll.

For more details on this situation, see our guide on Medicare and employer insurance.

Your Medicare Enrollment Options

When you enroll in Medicare, you'll need to make a key decision: Original Medicare or Medicare Advantage. This choice affects everything from your costs to which doctors you can see.

Option 1: Original Medicare + Medigap + Part D

This is the traditional approach that gives you the most flexibility:

• Part A (Hospital Insurance): Covers hospital stays, skilled nursing, hospice. Usually premium-free if you paid Medicare taxes for 10+ years.
• Part B (Medical Insurance): Covers doctor visits, outpatient care, preventive services. Standard premium is $185/month in 2025.
• Part D (Drug Coverage): Covers prescription medications. Premiums vary by plan (average ~$35/month).
• Medigap (Medicare Supplement): Private insurance that covers your share of costs like deductibles and coinsurance. Premiums vary by plan and location.

Best for: People who travel frequently, want to see any doctor who accepts Medicare, or have chronic conditions requiring specialist care.

Option 2: Medicare Advantage (Part C)

Medicare Advantage plans are offered by private insurers and replace Original Medicare:

• Often include Part D drug coverage
• May offer extra benefits (dental, vision, hearing, fitness)
• Many have $0 premiums (beyond your Part B premium)
• Use provider networks (HMO, PPO, etc.)
• Require prior authorization for some services

Best for: People who want lower upfront costs, don't travel much, and are comfortable with network restrictions.

How to Enroll in Medicare: Step by Step

The enrollment process is straightforward once you know the steps. Here's exactly what to do:

Step 1: Enroll in Part A and Part B

You have three options:

1. Online: Visit ssa.gov/benefits/medicare and create or log into your my Social Security account
2. Phone: Call Social Security at 1-800-772-1213 (TTY 1-800-325-0778)
3. In person: Visit your local Social Security office

What you'll need:

• Your Social Security number
• Date and place of birth
• Current employer information (if still working)
• Dates of any employer coverage you've had

Step 2: Decide on Original Medicare vs. Medicare Advantage

Once enrolled in Parts A and B, you automatically have Original Medicare. You can then either:

• Stay with Original Medicare and add a Medigap policy and Part D plan
• Switch to Medicare Advantage during your Initial Enrollment Period

Step 3: If Choosing Original Medicare, Enroll in Medigap

Your Medigap Open Enrollment Period is crucial: it's the 6-month period starting when you're 65+ AND enrolled in Part B. During this window:

• Insurance companies can't deny you coverage
• They can't charge more due to health conditions
• You have guaranteed issue rights

Step 4: Enroll in Part D (Drug Coverage)

If you choose Original Medicare, you'll need a standalone Part D plan. If you choose Medicare Advantage, drug coverage is usually included.

Compare Part D plans at Medicare.gov/plan-compare. Enter your medications to see which plan offers the best coverage at the lowest cost.

Understanding Medicare Enrollment Periods

Medicare has several enrollment periods, each with specific rules. Here's when you can make changes:

For complete details on every enrollment window, see our Medicare Enrollment Periods guide.

Common Enrollment Mistakes to Avoid

These mistakes cost people thousands of dollars every year. Don't let them happen to you:

Mistake #1: Missing Your Initial Enrollment Period

If you miss your IEP and don't have qualifying coverage, you'll face:

• A 10% Part B penalty for each 12-month period you delayed
• This penalty is permanent and added to your premium for life
• You must wait for the General Enrollment Period (Jan 1 - Mar 31) to enroll
• Coverage won't start until July 1

Mistake #2: Thinking COBRA Counts as Employer Coverage

COBRA is not considered employer coverage for Medicare purposes. If you turn 65 while on COBRA, you must enroll in Medicare during your IEP or face penalties.

Mistake #3: Skipping Part D

Even if you don't take medications now, skipping Part D can be costly. The late enrollment penalty is 1% of the national base premium ($34.70 in 2025) for each month you went without creditable drug coverage. This penalty is also permanent.

Mistake #4: Choosing Medicare Advantage Without Researching

Medicare Advantage plans often have $0 premiums, which makes them attractive. But before you choose one, make sure:

• Your doctors are in the plan's network
• Your medications are covered
• You understand the prior authorization requirements
• You're comfortable with the out-of-pocket maximum

Learn more in our article on 7 costly Medicare enrollment mistakes.

Where to Get Medicare Enrollment Help

You don't have to navigate Medicare alone. Here are free and paid resources:

Free Resources

• SHIP (State Health Insurance Assistance Program): Free, unbiased counseling in every state. Find yours at shiphelp.org
• Medicare.gov: Official plan comparison tool and enrollment information
• Social Security: Can help with Part A and Part B enrollment
• 1-800-MEDICARE (1-800-633-4227): 24/7 help line for general questions

Paid Resources

• Insurance brokers: Help you compare plans at no cost to you (they earn commissions from insurers)
• Fee-only Medicare advisors: Provide unbiased advice for a flat fee with no insurance company ties

Your Medicare Enrollment Checklist

Use this checklist to ensure you don't miss anything:

1. 6 months before turning 65: Start learning about your Medicare options
2. 3 months before turning 65: Enroll in Part A and Part B through Social Security
3. Within first 3 months of IEP: Decide between Original Medicare and Medicare Advantage
4. If choosing Original Medicare: Shop for and enroll in a Medigap policy during your 6-month open enrollment
5. If choosing Original Medicare: Compare and enroll in a Part D plan
6. If choosing Medicare Advantage: Compare plans and enroll in one that covers your needs
7. After enrolling: Keep all Medicare paperwork and cards in a safe place
8. Every year (October 15 - December 7): Review your coverage during the Annual Enrollment Period