Retiring After 65? 5 Scenarios When You Shouldn’t Wait to Enroll in Medicare

Medicare is health insurance for people 65 and older.* You qualify for Medicare if you have worked and paid Medicare taxes for 40 quarters (10 years). 


Even if you are working past the age of 65 and getting health insurance from your employer, you can still enroll in Medicare if you qualify. Sometimes, it can actually benefit you to enroll at 65.


Let’s look at 5 scenarios when enrolling in Medicare may be a better decision than staying on your employer’s health plan.
 

Good to know: Part A and Part B are together known as “Original Medicare.”

*Or people younger than 65 who  have a disability, end-stage renal disease (ESRD), or ALS (also called Lou Gehrig’s disease).

5 Scenarios for Enrolling in Medicare

Comparison is key. Depending on the plan options offered by your employer, choosing to enroll in Medicare (including a Medicare Advantage or Medicare Supplement plan) could be a more cost-effective option and/or provide more comprehensive coverage overall.


It all depends on your individual health care needs and budget.

Medicare is not a free service. But, in most cases, neither is your employer’s health insurance plan.
A premium is the amount you pay each month to be a member of a health insurance plan. Look at these Medicare premiums and compare them to the plan(s) offered by your employer:

  • Part A (hospital insurance) is $0 a month for most people. However, if you don’t qualify for premium-free Part A (because you or your spouse did not pay taxes long enough while working — generally at least 10 years), the premium for 2025 is either $285 or $518 a month, depending on how long you or your spouse worked and paid Medicare taxes.
  • Part B (medical insurance) is $185 a month for 2025. But this could be higher depending on your salary.
  • Part C (Medicare Advantage plans) can vary. Medicare Advantage plans are offered by private health insurance companies. They include Part A, Part B, and usually Part D, and typically offer additional coverage for items and services not covered by Original Medicare. Though you are still responsible for paying your Part B premium, you may be able to find Medicare Advantage plans with $0 monthly premiums.
  • Part D (prescription drug plans) can vary. Part D plans are also offered by private health insurance companies, so your exact monthly premium will vary by plan. If you join a $0 premium Medicare Advantage plan that includes drug coverage, you can get Part D coverage for $0 a month.

 

What do the four parts of Medicare cover?

Aside from your monthly premium, you also pay for health insurance in the form of cost sharing—which includes deductibles, copayments, and coinsurance.


A deductible is an amount of money that you’re responsible for paying out-of-pocket each year before your plan begins paying for covered services. For example, if you have a $1,000 medical deductible, you must pay $1,000 out-of-pocket before you plan pays for any medical services.

 

Medicare Advantages plans may have lower or $0 medical and prescription drug deductibles. (Original Medicare, on the other hand, has deductibles for both Part A and Part B.)

 

What are copayments and coinsurance?
 

Generally speaking, you get more comprehensive coverage by enrolling in a Medicare Advantage plan (or in Original Medicare plus a Medicare Supplement plan) than by enrolling in Original Medicare. 

 

What is a Medicare Supplement Plan?

 

Medicare Advantage plans cover everything that Original Medicare covers, plus more. Though exact benefits vary by plan, this can include dental coverage, vision coverage, hearing aids coverage, prescription drug coverage, and more. Compare your employer’s plan to the Medicare Advantage and/or Medicare Supplement plans you are considering.

 

What does Original Medicare cover and not cover?

Employers sometimes offer this option because it is more cost effective for them than offering you an employer-sponsored plan.

Retiree coverage is insurance offered by employers to employees after they retire. If your employer offers this, you may be required to sign up for Part A and Part B to receive these benefits. Ask your Human Resources (HR) department how your retiree coverage works with Medicare.


Retiree coverage plans work similarly to Medicare Supplement plans in that Medicare pays first, then then the plan helps cover the “gaps”—such as coinsurance and deductibles.


Before enrolling in retiree cover, ask your HR department:

  • If you (or your family’s) current benefits will change
  • If they offer creditable drug coverage (coverage that's expected to pay, on average, at least as much as Medicare drug coverage). This is important for you to have adequate coverage and avoid paying a late enrollment penalty when you enroll in a Medicare Part D plan. Your plan must send you information each year about whether your drug plan is considered creditable. (Keep this information in case you need it when you’re ready to join a Medicare Part D plan.)