We hear a lot of the same questions over and over. It tends to happen when you’ve been in business as long as we have and you’ve helped as many retirees and soon-to-be-retirees with their planning as we have. We thought it would be a good idea to answer a couple of these questions every week.
Please note this very important fact. Our answers do not take into account your particular investment objectives, financial situation, or risk tolerance and may not be suitable for all investors. Our answers are not financial advice and should not be taken as advice. This material is provided for educational purposes only.
Do I have to take Medicare at age 65?
When talking about filing for Medicare and whether or not you need to file for Medicare when you turn 65, the short answer is: it depends. It depends on if you have coverage through your employer. It depends on if you have coverage from a spouse’s employer. It depends on the size of the employer providing coverage. It depends on if you have some coverage elsewhere. While 65 is the “magic number” for Medicare eligibility, you aren’t always forced to enroll immediately, but making the wrong choice can lead to permanent late-enrollment penalties.
If you or your spouse are still working and covered by an employer group health plan, the size of the company will be the deciding factor. If the employer has 20 or more employees, the insurer will more than likely require you to enroll in Medicare Part A, but you can usually delay Medicare Parts B and D without penalty. In this scenario, your employer plan remains your “primary” insurance. However, be careful: if you have a High Deductible Health Plan with an HSA, enrolling in any part of Medicare stops your ability to contribute to that HSA.
If the employer has fewer than 20 employees, Medicare usually becomes the “primary” payer at age 65. In this case, you will almost certainly need to enroll in Parts A, B, and D immediately as your small-group plan may refuse to pay for services that Medicare would have covered.
Quick sidebar on the parts & coverages of Medicare:
| Medicare Part | Summary of What Is Covered |
|---|---|
| Part A | Hospital Insurance – covers inpatient care in hospitals, skilled nursing facilities, hospice care, and home health care. |
| Part B | Medical Insurance – services from doctors and other health care providers, outpatient care, home health care, durable medical equipment, and preventative services. |
| Part D | Drug Coverage – pharmacy drug coverage, will vary by plan |
| Medigap | Extra insurance you can buy from private companies that helps pay your share of Medicare and fill in gaps. |
| Part C Medicare Advantage | Private insurance acting much like an employer-provided PPO plan. |
The rules for Affordable Care Act (aka ACA or Marketplace) coverage are different. Once you are eligible for Medicare, you generally lose any premium tax credits or subsidies for your ACA plan. While you can technically keep an ACA plan, it is almost always financially disadvantageous to do so. Furthermore, keeping an ACA plan instead of enrolling in Medicare at 65 does not count as “creditable coverage,” meaning you would face late-enrollment penalties should you eventually switch to Medicare later. Making the decision for you, your ACA provider may cancel your plan when you turn 65 and all providers are prohibited by law from offering you a new ACA plan once you are eligible for Medicare.
The same “no-go” rule applies to COBRA or retiree insurance; neither is considered “current employment” coverage. If you are on COBRA or a retiree plan, you must sign up for Medicare during your Initial Enrollment Period to avoid gaps in coverage and lifelong surcharges. When in doubt, check with your benefits administrator to see how your specific plan coordinates with Medicare.
If you are a veteran or a Federal employee, your situation depends on the coverage you have and the coverage you plan to keep. If you are retired military and are eligible for TRICARE For Life, you are required to file for Medicare Parts A and B. If you are a Federal employee and have your coverage through Federal Employees Health Benefits Program (FEHB… probably Blue Cross Blue Shield), you can keep this coverage in retirement and do not have to file for Medicare when you turn 65. Further, your FEHB counts as credible coverage so long as you have it, so if you drop it in the future and want to file for Medciare later than 65, you may do so without penalty.
How can I invest more in my retirement accounts?
A lot of folks put what they can in their employer-sponsored retirement account (401(k), 403(b), 457, TSP, etc.) and IRAs and don’t pay attention to them—then panic when retirement gets close and they look to see a small balance and little gains for their trouble. If you feel behind on retirement savings—or simply want to take full advantage of your tax-advantaged accounts—and want to know how to invest the most in your retirement accounts, the IRS gives you several ways to accelerate contributions especially as you approach retirement.
Before we talk about additional contributions, make sure you are maxing out the standard contribution limits for your employer-sponsored retirement accounts ($24,500 for 2026) and IRAs ($7,500 for 2026). Then, once you hit age 50 you become eligible for catch-up contributions, which allow you to contribute above the normal annual limit. For many workers, this is the easiest and most powerful way to boost savings during peak earning years. For 2026, your standard catch-up contributions are $8,000 for employer-sponsored accounts and $1,100 for IRAs, bringing them up to $32,500 and $8,600, respectively.
Then there is the “super catch-up.” If you are between ages 61 and 64, you can contribute an even larger catch-up amount to your employer-sponsored plan. This provision was designed to help individuals who may be nearing retirement but need to make up for earlier gaps in saving. The super catch-up for 2026 is an additional $3,250 on top of the regular catch-up for employer-sponsored plans, for a total of $11,250 in catch-up contributions.
However, there is an important twist for higher earners. If your wages exceed a certain threshold (currently set at $150,000, indexed for inflation), any catch-up contributions to a 401(k) must be made into the Roth portion. That means you won’t get a tax deduction today, but those contributions—and their future growth—can be withdrawn tax-free in retirement, assuming you meet the rules. If an employer doesn’t offer a Roth, the high-earning employee cannot make any catch-up contributions.
The key to investing more in your employer-sponsored retirement accounts is to be intentional. These enhanced contribution limits are time-sensitive opportunities. Taking advantage of catch-up and super catch-up provisions in your early 60s can meaningfully improve your long-term financial security and give your retirement plan a final, powerful boost.