Turning 65 or Retiring Soon? Receiving SSDI?

If you’re enrolling into Medicare within the next 6 months or have questions about your current plan, Insurance With Don is here to help! We can help you navigate the complexities of Medicare, recommend the best options for your specific needs, and answer questions about all of the changes happening with Medicare every year.

We’ve compiled 100s of resources to teach you everything you need to know about Medicare, the yearly changes, and what your options are for coverage. You can also set an appointment with us to have a 100% FREE Medicare Consultation!

How Medicare Works

There’s a few different circumstances that will make you eligible to receive Medicare benefits. This includes turning 65, retiring and dropping your employer sponsored health insurance, receiving Social Security Disability Income (SSDI) for 24 months, and certain qualifying health conditions (ESRD, ALS, etc.)

Original Medicare is separated into 2 parts, Part A and Part B. These cover your doctors and hospital bills but they don’t cover 100% of your costs or prescription drugs, and can leave you with very expensive deductibles and co-insurance (with no yearly limits). By utilizing a Medicare Supplement Plan paired with a Prescription Drug Plan (Part D) or a Medicare Advantage Plan (Part C) that includes your Part D coverage, we can lower your exposure to expensive hospital and drug costs that you’d experience by having Original Medicare only.

How to Enroll Into Medicare

The enrollment process will be different for everyone depending on their circumstances. Automatic enrollment occurs for some individuals, while others will need to manually enroll, or even opt to delay Medicare depending on their retirement status and Health Savings Account (HSA) contributions.

Automatic Enrollment

Enrollment may be automatic for those who have received Social Security/Railroad Retirement Board Benefits at least 4 months prior to their 65th birthday. Individuals receiving Social Security Disability Income for a consecutive 24 months will also be automatically enrolled. Additionally, if you have Lou Gehrig’s disease (ALS), you’ll be automatically enrolled when you start receiving disability benefits. 

Social Security Office

You can enroll into Medicare Part A and B at your local Social Security office in person or over the phone. If you’re already enrolled into Part A you can enroll into Part B by mailing in CMS Form 40B to your local office. If you’re retiring and delayed Medicare past your 65th birthday you will need to also submit CMS Form L-564 to show that you had creditable coverage through your employer while delaying Medicare.

Online Medicare Enrollment

You can enroll into Medicare Parts A and B, as well as Social Security, online at SSA.gov. The process is straightforward and takes roughly 15 minutes. We can assist you with this if needed!

When to Enroll Into Medicare

You will have an Enrollment Period available to you depending on your specific circumstances. Here’s a list of the different enrollment periods available:

Initial Election Period (IEP)

When you turn 65 years old you have an enrollment period that is a 7 month window of your birthday to enroll into Medicare Parts A&B. This would be 3 months before, the month of, and 3 months after your birthday. You will have the same period available to you if you have received Social Security Disability Income (SSDI) for 24 months. This period will be 3 months prior to the 25th month, the month of, and 3 months after.

Special Election Period (SEP)

For those who kept employer sponsored health insurance or a spouses work insurance past 65, you will have an enrollment period available once employer coverage is dropped. You will have 8 months after dropping employer coverage to enroll into Medicare A&B (if you haven’t opted into Part A already). Beware that you only have a 63 day period to enroll into a Prescription Drug Plan (Part D) after losing creditable coverage to avoid penalties!

Annual Enrollment Period (AEP)

Every year we have an annual enrollment period that we can use to enroll you into a Medicare Advantage Plan (MAPD). This period ranges from October 15th to December 7th.

Open Enrollment Period (OEP)

Open enrollment is a yearly period that we can switch you from a like plan to a like plan (MAPD to MAPD). This period can be used if you aren’t satisfied with your current Medicare Advantage plan to move to one that better suites your needs and budget.

Depending on your eligibility, we can utilize your enrollment period to enroll you into either a Medicare Supplement (Medigap) Plan or a Medicare Advantage Plan, based on your health needs and budget. There’s also Annual Enrollment Periods (AEP) and Open Enrollment Periods (OEP) that can be used to enroll or switch Medicare plans. We can also assist in enrollment for cost savings programs such as Extra Help/Low-Income Subsidy and Medicaid. We’ll be able to consult you on the best options for you and ensure that your doctors are in network, and your prescriptions are on a plans formulary, prior to enrolling you into any plans!

Original Medicare

Original Medicare is a federal health insurance program offered to individuals 65 years or older, certain qualifying health conditions, and those receiving Social Security Disability Income for over 24 months. Medicare is broken up into Parts A and Parts B that cover you for your hospital and medical expenses. Medicare has a broad network that you can utilize for doctors and hospitals, but has high out of pocket exposure on its own. This is why we recommend pairing Medicare with either a Supplement Plan or Advantage Plan. You will also need a Part D Prescription Drug Plan if you opt for Original Medicare only, a Supplement Plan, or a Medicare Advantage without Part D included.

Part A Hospital Insurance

Part A has no monthly premium if you have worked at least 10 years or 40 quarters, or a spouse has. Part A covers you for inpatient services, skilled nursing facilities, home healthcare and hospice. Part A has a deductible that covers you for the first 60 days that you are hospitalized.

Part B Medical Insurance

Part B has a monthly premium of $185 in 2025 for most people, a yearly deductible of $257, and a 20% coinsurance for any medical services. Part B must be paid unless you qualify for Medicaid or other programs that assist with the cost of Original Medicare. Part B will cover your doctors, outpatient care, some home health services, some durable medical equipment and prescriptions, and some preventative services.

Medicare Supplement (Medigap)

Medicare Supplement Plans offered by private insurance companies can fill in the gaps of Original Medicare (Parts A&B), protecting you from large hospital bills. Medigap plans are standardized, meaning that no matter what carrier you choose they will offer the same basic benefits. Plans are categorized by letters A-N, with different levels of coverage between each letter. With a Medicare Supplement plan you can go to any doctor that accepts Medicare, with no referrals or preauthorization needed.

Medicare Advantage (Part C)

Medicare Advantage Plans are offered by private insurance companies, taking over for Original Medicare (Parts A&B). With Medicare Advantage Plans your prescription drug coverage is often included, as well as extra perks such as gym memberships, groceries, and over the counter allowances (not all plans). Some plans even include dental and vision.

Medicare Advantage plans are offered as an HMO, PPO, or PFFS meaning that Doctor’s and Specialists can choose to accept a plan. Plans have changes every year, which is why its recommended to have an agent that can compare plans every year for you. We can ensure your doctors & specialists are in network, as well as check your prescriptions on the plans formulary (list of covered drugs).

Prescription Drug Plans (Part D)

If you’re enrolled into Original Medicare, utilizing a Medicare Supplement Plan, or an Advantage Plan with no Part D include, you will need a Medicare Part D Prescription Drug Plan for your prescription drug coverage. This can be a stand alone plan, or included in your Medicare Advantage (Part C) plan.

Medicare Part D Plans have a monthly premium for coverage, a yearly deductible, as well as a maximum out of pocket that will limit your yearly costs for prescriptions.

How to Save Money on Medicare Costs

Extra Help/Low-Income Subsidy

LIS or Extra Help is a federal program that assists individuals with limited income and resources with the cost of their Part D prescription drug coverage. LIS can assist with premiums, deductibles and copayments for Part D. You may need to apply for LIS if you are not automatically deemed eligible (receiving Medicaid or Supplemental Security Income). You must be enrolled into Part D in order to receive LIS, and if your income or resources change you can lose eligibility for assistance.

Medicaid (Dual Special Needs Plans)

Medicare can be paired with Medicaid in order to help you save money on copayments, coinsurance and some services that Medicare doesn’t cover. When you have Medicare and Medicaid you are also eligible for Dual Special Needs Plans (DSNP) that offer extra benefits such as dental, vision and hearing as well as Over The Counter Benefits.

Medicare Advantage Plan

Medicare Advantage Plans can help you save money on your Medicare costs with low to $0 per month premiums for most plans and extra benefits such as dental, vision and hearing as well as grocery/over the counter benefits. Medicare Advantage plans may also include transportation allowances, benefits that can be used on utility bills, and gym memberships.