Insurance Checklist: What to Do Before Your Military Transition

Leaving the military is a major life change. Confirming your insurance coverage is an essential part of post-military life that you can’t get wrong. Not planning properly could leave you without the protections you need. With a strong insurance checklist guiding your every step, you can protect your health, income, and family as you leave the military and move into civilian life.

Please note that this article is aimed at assisting those who are separating from the military, rather than retiring. We have highlighted the areas where benefits differ based on your status. 

Why Insurance Planning Matters During Transition

Insurance planning is a key part of your military-to-civilian transition because many of the benefits that you enjoyed while in the military may not automatically carry over. This can create gaps in coverage and present significant financial exposure and strained budgets because of higher premiums and out-of-pocket expenses. 

Insurance planning matters during your transition to:

• avoid dangerous gaps in health coverage (TRICARE coverage can lapse at separation).
• manage pre-existing military-related health issues.
• replace Servicemembers’ Group Life Insurance (SGLI) with appropriate long-term coverage.

Proactive planning, including having a comprehensive checklist, can prevent these gaps, protect your family’s finances, and manage the higher cost of private-sector insurance.

Life Insurance Checklist

While on active duty, you had SGLI, which offered you low-cost life insurance coverage. If you had a family, they were covered under Family Servicemembers’ Group Life Insurance (FSGLI). 

Here is how you can navigate your life insurance situation as you approach leaving the military: 

SGLI: Once you separate from the military, you have 120 days of free coverage before it lapses. Veterans can apply for VGLI within 240 days of separation without proof of good health. You then have one year, in addition to the 120 days, to convert your SGLI to Veterans’ Group Life Insurance (VGLI). This option allows you to keep your life insurance coverage as long as you keep paying the premiums. 

FSGLI: You can convert spousal FSGLI coverage to a permanent insurance policy, like whole life, within 120 days of your separation. To convert, you must choose a participating company, apply at their local sales office, and provide proof of FSGLI coverage

Private Insurance: You can convert SGLI coverage to an individual policy within 120 days from discharge without proof of good health. Check out the list of participating companies and how to convert. 

Health Insurance Checklist

Separating from Active Duty

Most separating service members (remember, separating from active duty is different from retiring) lose TRICARE at separation. Ideally, you will have a new job lined up before you separate, and you can sign up for civilian healthcare provided by your new employer. Depending on your benefits, this may serve as primary coverage for you and your family. 

Pro Tip: There will probably be a waiting period before your new employer’s health insurance kicks in, so you may need temporary coverage options. Check out your options below.

Here is how you can navigate your health insurance situation as you approach leaving the military: 

Transitional Assistance Management Program (TAMP): If you are a separating service member who was involuntarily separated or leaving under qualifying conditions, you may be eligible for TAMP. TAMP provides up to 180 days of premium-free TRICARE coverage to qualifying separating service members and their families. If you qualify, you are generally enrolled when you separate.

The Continued Health Care Benefit Program (CHCBP): CHCBP is a premium-based plan that provides temporary coverage when you lose eligibility for TRICARE upon separation as a bridge to civilian coverage. You have to purchase CHCBP within 60 days of leaving the military, and coverage only lasts 18 months (up to 36 months for some qualified spouses and others). According to TRICARE, you enroll in the program by submitting DD Form 2837 and the first 90-day premium payment within 60 days of losing TRICARE eligibility. 

Veterans Affairs Health Care: You may be eligible to receive health care benefits at a VA medical care facility. Eligibility for VA healthcare benefits is based on several factors, including active-duty service, type of discharge, income, service dates, and deployments. Having a service-related disability increases priority, but isn’t required.  

The Healthcare Marketplace: If you don’t qualify for TRICARE, VA health care, or private insurance through your employer, you can buy health insurance from the Health Insurance Marketplace. The marketplace provides several plans; some may even offer subsidies based on your income.

Private Insurance: If you prefer certain providers or additional coverage options that you can’t find in any of the other available options, you can get private insurance. That way, you will be able to tailor the plan that meets your individual needs.  

Retiring from the Military

If you have served your country and qualify for retirement, great job! I know that when I retired, I knew that my family’s health insurance needs would be met through TRICARE, and that we would save a substantial amount of money on our health care needs.

Here is a checklist of your retirement health care options:

TRICARE Prime: A managed-care plan only available in Prime Service Areas. There are lower out-of-pocket costs, but you have to have a Primary Care Manager (PCM) and referrals for specialty care. 

TRICARE Select: A preferred provider option (PPO), TRICARE Select offers more freedom to choose a provider without referrals, but has higher deductibles, cost-shares, and enrollment fees.

TRICARE for Life (TFL): Once you reach age 65, you are eligible for TFL, which is used as a secondary insurance after Medicare. I just went through this process, and it’s painless. You just sign up for Medicare through your Social Security portal, and you will be notified when it has all been processed.

TRICARE Retired Reserve: If you are a retired member of the Guard or Reserves qualified for a non-regular retirement and not yet 60 years of age, you may be eligible.

Military Retiree Dental Care and Vision Insurance: Dental and vision insurance are offered to military retirees through the FEDVIP program. You will pay a premium each month for both.

Auto Insurance Checklist

When leaving the military, there are a few things you need to do to ensure that there is no lapse in coverage during your transition. 

Here is how you can navigate your auto insurance situation as you approach leaving the military: 

• Update Your Address: Premiums are based on location.
• Update Vehicle Usage and Mileage: If you are commuting to work, this changes your risk profile.
• Do an Auto Insurance Review: This includes getting quotes from different companies.
• Update Your Vehicle Registration (particularly if you’re moving to a new state).
• Review Liability Coverage and Bundling (especially if moving from on-base housing to a home you own). 

Renters/Home Insurance Checklist

You will also want to review your renters/homeowners insurance as part of your transition checklist. You might want to shop around, especially if you are moving to a different state. Your current agent may not operate in your new location. 

• Complete a Comprehensive Home Inventory: Determine how much coverage you really need. Make sure to itemize all high-value and hard-to-replace items. When applicable, record serial numbers and retain receipts. 
• Shop Around: Compare rates from multiple companies.
• Notify Your Agent You Have Left the Military: This may affect your risk profile. 
• Consider Bundling Policies: Combining homeowners/renters and auto policies can save you money. 
• Update Address and Coverage: Ensure you have full replacement costs, rather than market value, verify liability limits, update coverage limits, and adjust your deductible based on your budget.  
• Verify Storage Coverage: Ensure items in storage are covered during your transition.

Timeline: What to Do Before and After Separation

Health Insurance Checklist

Pre-Separation (90 to 180 days) 

• File your Benefits Delivery at Discharge (BDD) Claim: If you are filing for VA disability, this is the most crucial step to get benefits faster.  
• Complete a Separation Health Assessment (SHA): This self-assessment documents all occupational exposures and injuries. Confirm your military separation physical.
• Gather Medical Treatment Records: Collect all medical, dental, and mental health records.
• Register for MHS GENESIS: Ensure you have access to the MHS GENESIS Patient Portal to download your records.
• Review Your Health Insurance Options: Investigate post-separation coverage, including:

• Transitional Assistance Management Program (TAMP): Provides 180 days of premium-free health care.
• Continued Health Care Benefit Program (CHCBP): Temporary premium-based coverage after TRICARE/TAMP expires.
• VA Health Care: If you have a service-connected disability, you may be eligible for VA health care.
• TRICARE: If you are retiring and qualify for TRICARE Prime, Select, or Reserve Select.

Upon Separation (0 to 120 days)

• Confirm DEERS information is current: This will avoid coverage gaps.  

• Enroll in CHCBP (if necessary): If you are not eligible for TAMP and have no employer insurance, apply for the CHCBP within 60 days of losing TRICARE/TAMP.
• Apply for VA Health Care: If you determine this is your best option, and you qualify, apply for VA health care.  
• Select New Plan: If not using TAMP/CHCBP, select and activate your new employer or Marketplace plan.

After Separation (180 Days to 2 Years)

• Enroll in CHCBP: If you do not have employer coverage after TAMP benefits end (180 days), you can buy CHCBP for 18 to 36 months of additional coverage. You have 60 days to enroll after losing TAMP/TRICARE.

Life Insurance Checklist

Pre-Separation (90 to 180 days)

• Determine SGLI Conversion Options: Decide between converting to VGLI or purchasing a commercial policy.
• Apply for VGLI (Optional): If you apply for VGLI within 240 days of separation, you do not need to prove good health. After 240 days, and up to 1 year later, you will have to complete a medical exam.
• Convert SGLI to Whole Life: You can convert SGLI to a permanent policy (often whole life) with a commercial company within 120 days of separation.
• Check Spouse Coverage: FSGLI ends 120 days after separation. During that period, you can convert it to a commercial policy.

Upon Separation (0 – 120 days)

• Review SGLI Coverage Amount: Identify your current coverage level on your final Leave & Earnings Statement (LES).  
• Confirm Separation Date: Know the exact date to calculate your 120-day SGLI extension and 240-day VGLI guaranteed enrollment window.
• Decide on VGLI: Determine if you will convert SGLI to VGLI.  
• Evaluate Private Insurance: Compare VGLI premiums with commercial life insurance policies.

Common Mistakes

Using our insurance checklist can help prevent some of the common mistakes when leaving the military:

• Letting SGLI Expire: Failing to convert to VGLI or a private policy will eliminate your safety net. SGLI coverage ends on day 121 after separation, and you have an additional one year to convert. If you convert after 240 days, you have to have a medical exam.
• Assuming Coverage Continues: If you want to use VA health benefits, you have to apply. Coverage does not automatically switch from TRICARE. 
• Failing to Shop Around: Relying on the same insurance company for all your insurance needs can lead to higher out-of-pocket expenses.
• Making Last-minute Decisions: Rushing into buying life or health insurance without careful research can cost you dearly.
• Missing Application Deadlines: You have deadlines you must meet to receive VA benefits, such as disability compensation. 

Bottom Line

A successful transition out of the military requires planning to ensure you protect your health, your family, and your financial future. Using our insurance checklist and avoiding common mistakes, such as missing deadlines, you can avoid costly gaps and replace the coverage you lose once you leave the military. Being proactive ensures you make the successful transition to civilian life with all of the insurance protections you enjoyed while in uniform.