Hello there! 

Approaching the milestone age of 65 can feel overwhelming with the constant phone calls, junk mail, and non-stop ads promising you the world — these can be frustrating, confusing, and often misleading. Medicare isn’t a one-size-fits-all design, yet most of these callers and ads only offer a one-size-fits-all approach (and it’s for their benefit, not yours.) Even worse, they could be scammers or fraudsters…but there’s no way to tell without a proper vetting process. Why take that risk?

Don’t fall for these traps! Work with experienced professionals with decades of service to communities in your area, who will always have your best interest in mind, respect your privacy and Protected Health Information, and provide expert personalized guidance to ensure you made the best decision for your retirement.

Whether you’re turning 65 soon or you’re over 65 and need to start thinking about Medicare, we’ve created this Frequently Asked Questions page just for you. As always, our experts are here to help you make informed decisions about Medicare—no pressure, no gimmicks or nonsense guaranteed!

Medicare FAQ

If you or your spouse are actively working for a company with 20 or more employees and are covered under a qualified group health insurance plan, you can delay enrolling in Medicare until the job or health coverage ends, with no penalties or loss of options.

After losing this job-based coverage, you have a special enrollment period of eight months to sign up for Medicare without a penalty.

If your employer has fewer than 20 employees, you will need to enroll in Medicare when you’re eligible. If you don’t, you could face lifetime penalties and coverage gaps!

If you can delay Medicare enrollment, it is still prudent to look at all of your options to make sure you didn’t leave anything on the table. Sometimes Medicare offers lower insurance rates and/or more benefits than employer group coverage. You have the choice to:

1. Continue to use your employer’s health plan and delay Medicare enrollment.
2. Enroll in Medicare and drop the employer’s coverage (if Medicare is better than your current coverage).
3. Use both the employer’s coverage and Medicare (often this leads to being over-insured).

Medicare coordinates differently with COBRA than it does with active employer coverage. When you are still actively working at a large employer, their Group Insurance pays primary and Medicare pays secondary.

The opposite is true of COBRA: Medicare pays first and COBRA pays second. What this means is that if you do not enroll in Medicare when first eligible, YOU will be the primary payer, and unless your name is Jeff Bezos and have an unlimited supply of money, we recommend to enroll in Medicare when eligible.

If you’re on COBRA first and then become eligible for Medicare, you must enroll in both Medicare Part A and Part B during your Initial Enrollment Period (IEP). Once your Medicare starts, your COBRA typically ends. If you miss this enrollment period for Medicare, you will face lifetime penalties! On the bright side, your dependents can keep COBRA for up to three years, even after you switch to Medicare.

If you enroll in Medicare first and then enroll in COBRA,  the good news is that you can have both. Taking COBRA is optional, and depending on your situation, you may or may not want to. If you do decide to take COBRA, do not drop your Medicare plan. Medicare is your primary insurer, and that won’t change when you take COBRA. Medicare will cover some or all health care costs first. COBRA may pay some costs not paid for by Medicare.

Possibly! If you are already receiving Social Security benefits, Railroad Retirement benefits, Social Security Disability, or Railroad Disability at least four months before your 65th birthday, you’ll be automatically enrolled in Medicare at 65. However, if you’re not receiving any of the above benefits and you turn 65, you will not be automatically enrolled and will need to do so manually.

Remember, this is only for Part A and B of Medicare, not any additional coverage options like Medigap or Advantage plans, as those are never automatic enrollments. 

This is a subject that we could discuss for weeks and still have things left to cover. The decision to choose between Advantage or Supplement is a very personal decision and it is impossible for us to say which is better for you, without knowing you personally.  There is no “best plan”. We use a proprietary process for deciding the best Medicare path for each individual we help, and it would be inappropriate for us or anyone to tell you which path to choose without having a discussion about you, your health, your budget, your family history, etc. 

Both programs have pros and cons, and it’s a good idea to have an expert to help assist you with these important decisions. 

Most people don’t receive a bill from Medicare because the premiums are automatically taken from their Social Security or Railroad Retirement benefit.

If you’re not receiving Social Security benefits or Railroad Retirement benefits, you will be billed quarterly for Medicare Part B premiums. You will receive a paper bill in the mail towards the beginning of each month, and Medicare premiums are due on the 25th of each month.

You may pay your premium by mail or online at http://www.medicare.gov

Original Medicare Part A and B does not pay for routine dental care, such as cleanings, fillings, root canals, etc. 

Medicare Part A and B may cover dental work related to another health issue when medically necessary. This is called “Inextricably Linked Dental Services.” 

In layman’s terms, what this means is that some dental services are integral to other medically necessary treatments that the success of the treatment is dependent upon, or linked to the dental services in order to have a successful outcome for the treatments. 

For example, Medicare Part A and B will pay for dental or oral exams prior to heart surgery or organ transplant, or dental services needed to stabilize teeth related to a jaw fracture, or dental reconstruction due to a tumor surgery. 

On the other hand, Medicare Advantage plans usually DO include routine dental care for cleanings, fillings, and other routine services.

Unfortunately, the spam calls and junk mail have really gotten out of hand. These massive insurance companies have huge marketing budgets and can send non-stop mail to millions of people every year. 

Also, there are many call-centers across the globe who employ people just to sit on the phone all day and make thousands of calls using auto-dial software, just because they want to get to know you! Just kidding, they want to sign you up for a random Medicare plan and then couldn’t care less what happens after that. 

In a nutshell, the good people (like us!) don’t have to resort to these tactics as we follow ethical business practices an

Our recommendation: Hang up on these people immediately (or better yet, don’t even answer!), throw the mail directly into the trash, and schedule a call with someone who doesn’t harass people all day long!

Medicare Parts A and B generally do not cover prescription drugs that you would pick up at a pharmacy and administer yourself. This is where Medicare Part D (we like to say “D as in Drug”) coverage comes in. 

There are 2 ways to get prescription drug coverage through Medicare:

  1. Standalone Prescription Drug plan
  2. Medicare Advantage plan (Part C)

Most (not all) standalone drug plans are typically purchased to go along with your Medicare Part A and B coverage. This will add an additional monthly premium for the drug plan itself.

If you enroll in a Medicare Advantage plan that includes Part D coverage, you will have prescription coverage automatically added to your medical coverage (and at no extra cost to you).

Either way, you’ll need to choose a Medicare drug coverage option or else you’ll face lifetime penalty for not having a Part D plan!