“The most frustrating transition of my life!”

By Mark E. Overberg, Lt. Col., U.S. Army (Ret.)      August 2026

This story’s headline summarizes what many hundreds of military retirees told me about their experiences transitioning to Medicare at age 65.

In this story, I share my personal experience navigating the transition to Medicare after 14 years as the Deputy and then Director of Army Retirement Services. In this role, I consulted with military healthcare experts about TRICARE and MEDICARE and advised over a million retiring and Retired Soldiers through personal briefings and the Army Echoes and Change of Mission newsletters.

The purpose of TRICARE and Medicare

As much as military retirees like TRICARE, the “primary purpose of TRICARE is to support the medical readiness of the armed forces and the readiness of medical personnel.” The TRICARE program includes a comprehensive enrollment system for all categories of beneficiaries except TRICARE-for-Life (TFL) beneficiaries. TFL does not have an enrollment form or enrollment fee, because TFL coverage is automatic the first date a TRICARE beneficiary has Medicare Part A and Part B.

Medicare is the government healthcare program for Americans when they reach age 65. Medicare provides comprehensive medical coverage for the elderly and the disabled.” 

The more you learn about Medicare and the sooner you learn it, the smoother your transition to Medicare will be.

My personal healthcare insurance experience

My family and I used TRICARE Prime for 22 years while I was on active duty. When I retired, we shifted to the Federal Employee Program’s Blue Cross/Blue Shield (BC/BS) policy with TRICARE Select as our secondary insurance for the next 17 years. We also used TRICARE Young Adult for two years. Lastly, I started using Department of Veterans Affairs healthcare five years ago.

Advance notice about Medicare

Six months before I turned 65, the Defense Manpower Data Center (DMDC) mailed me a letter wishing me an early 65th birthday. DMDC reminded me that my retired ID card would expire on the first day of my 65th birth month and my Medicare decision was required before then as well. 

Medicare coverage starts on the first day of your 65th birth month unless you’re born on the first of the month. In that case, Medicare coverage starts on the first day of the month before your 65th birth month. DMDC encouraged me to renew my ID card online as soon as I made my Medicare election, so they could update my eligibility for benefits in the Defense Enrollment Eligibility Reporting System (DEERS).

Ninety days before my 65th birthday, the Social Security Administration (SSA) sent a letter reminding me it was time to make my Medicare decision. I was ready and made my election on the SSA website, at https://www.ssa.gov/ in less than 5 minutes.

Healthcare options for military retirees at age 65

Option A. For retired Department of the War (DOW) civilian employees with more than five years of civilian service, staying with their Federal Employee’s Health Benefit Plan (FEHBP) is their first option. DOW continues to pay a share of the civilian retiree’s monthly premiums. They also have the option to suspend their FEHBP with the option to re-enroll during an Open Season. Alternatively, if FEHBP is cancelled there is no option to re-enroll.

Option B. Opt into Medicare Part A and B and use TRICARE For Life (TFL) as secondary insurance for copays and prescription drugs. Most military retirees qualify for zero premium Medicare Part A (hospitalization) coverage because they paid into Medicare through payroll taxes for at least 10 years. Part B (outpatient care) is surprisingly expensive compared to TRICARE Prime because the premium is based on income and is paid by each enrollee. Retirees pay an Income Related Monthly Adjustment Amount (IRMAA) based on the Modified Adjusted Gross Income the retiree reported on their income tax form two years prior. TFL does not have an enrollment fee or monthly premium. For TFL, prior authorization (preapproval) is only required when TFL acts as the primary payer for certain specific medical services or skilled nursing care. When Medicare or another insurance plan is the primary payer, a TFL prior authorization is generally not needed.

Option C. Enroll in a Medicare Advantage (MA) plan (also called Medicare Part C). Civilian healthcare companies provide Medicare Part A and Part B benefits, 67 percent of MA plans have no monthly premium, however enrolees must pay their Medicare Part B monthly premium. MA plans often include prescription drug coverage and other benefits, such as a gym membership or dental services. While almost all plans with dental benefits cover routine preventive care, comprehensive care is tiered, subject to annual dollar limits, and dependent on the private insurance provider. MA Plans can afford to do this in part by requiring their enrollees to use in-network providers or pay higher copayments for out-of-network care. Most MA plans require preauthorization for many services. A recent Kaiser Family Foundation poll found most people view delays and denials of care by health insurance companies as a problem, with about two-thirds of Medicare beneficiaries reporting that they consider it to be a major problem.

Option D. Enroll in the Department of Veterans Affairs Healthcare, at https://www.va.gov/health-care/about-va-health-benefits/, which may charge for nonservice connected care depending on the enrollee’s qualifications. If the retiree’s spouse and eligible children are not veterans, they will need different healthcare insurance.

Some wrinkles

Each member of a military couple enrolls in Medicare just before their 65th birthday. Unless the retiree and their spouse have the same birth month and year, one of you will remain in TRICARE Prime or Select until the month they turn 65, while the other transitions to Medicare and TFL.

Medicare Part D (Prescription coverage)

Medicare Part D helps cover the cost of prescription drugs. TRICARE For Life beneficiaries remain eligible for TRICARE prescription drug coverage which is “creditable coverage” – at least as good as Medicare Part D prescription drug coverage, however, it does not provide identical coverage.

Medicare Supplemental Insurance (Medigap)

A “Medigap” policy generally covers the copays not covered by Medicare Part A and Medicare Part B, which normally covers 80% of allowable charges. There are several Medigap plans to choose from and their benefits and monthly premiums vary. TFL provides military retirees and their eligible dependents Medicare wrap around coverage and therefore most do not feel the need to enroll in a Medigap plan.

Summing it up so far

I’ve outlined:

• the timeline to enroll in Medicare and required actions military retirees should follow when TRICARE Prime and Select end at age 65.
• the most common choices for military healthcare insurance after age 65.

In the November edition of Army Echoes, I’ll explain the criteria I used to evaluate my healthcare insurance options after age 65. I’ll share my experience actually going through the transition process and some lessons learned that may make your decision and transition smoother. 

*Special thanks to Anne E. Breslin, TRICARE For Life program manager, Defense Health Agency for providing subject matter expertise to ensure the accuracy of this article.