The Comprehensive Military Retirement Checklist

Military retirement is a complicated time. You’re excited about what comes next, and worried about it, too. There are 100 things to do, from deciding where to live to figuring out your Tricare coverage to making sure that the service member’s disability claim is done properly. It can be overwhelming!

Fortunately, you’re not in this alone. I’ve gathered the best tips, tricks and suggestions from thousands of military service members and spouses to put together this checklist for you. I don’t claim that I have everything – this will always be a work in progress – so if you see something missing, please shoot me an email at kate@katehorrell.com with the subject line: retirement checklist.

As with all information on this website, this is not an official source. We gather and distill information so that’s easy to access and understand, but we can’t share every possible variation and exception. Always refer to official sources and verify that information provide applies to your unique situation.

Not every item on this list will apply to you, and that’s OK. Do a little research, and then disregard anything that doesn’t apply to your military retirement situation.

Most items link to a page that discussed the topic in more details, and provides links and resources.

More Than 2 Years Before Military Retirement

Consider going through the Transition Assistance Program (TAP) program a little earlier than the usual timeline. Personally, I think 3-5 years out is a great time to go through the program for the first time. The official guideline says to start within two years of retirement, or no later than 365 days before retirement. (Note: Having been in a TAP class with someone who waited until the last possible moment, I encourage you not to do that. He was beyond stressed.) If at all possible, spouses should also attend. Spouses have different questions than the service member, and remember different tidbits of information. Yes, this may mean taking off work or getting childcare, but it is worth it.

Start thinking about what life might look like after the military. Talk to your spouse, if you have one. This is an ongoing conversation that includes so many factors: jobs, climate, personal preference, schools, access to military resources, etc. In reality, many retiring military members end up going where they find a job. There’s nothing wrong with that, but if that’s what’s going to happen, it’s a lot easier to come to that conclusion earlier rather than later.

If you are married or have children, start learning about the Survivor Benefit Plan. For many families, this may be the biggest financial decision you ever make. There’s a lot to learn and you do not want to leave this decision to the last minute. If you’ve read and researched and still aren’t sure, consider getting help from a fee-only financial advisor who understands military pay and benefits. Be aware that there are many salespeople who will tell you that SBP is not right for you based on the desire to sell you life insurance or investments to replace SBP. SBP may or may not be right for your situation, but you don’t want to take advice on that from someone who stands to make money off your choice. SBP vs. life insurance vs. investments is not the right way to look at this question – they are different tools for different purposes.

Continue working on your transition fund.

If you don’t already have adequate post-retirement coverage, start looking into your life insurance options for the service member and spouse. Get this into place as soon as possible – do not wait until you’re starting the retirement and disability medical processes, and definitely don’t wait until after you retire. You can’t make good decisions about SBP and/or VGLI until you know whether you are insurable on the civilian market.

Identify any educational or employment programs that the service member or spouse may want to complete while still on active duty. Looking into offerings by:

Catch up on all the medical stuff that you’ve been avoiding. Make appointments to document all your medical issues, and make and complete specialty appointments, as necessary. That nagging shoulder or hearing problem or snoring that makes your whole family complain? Get the process started now.

If you own rental property, make sure you understand the military extension on the capital gains exclusion. You may want to sell that property before or shortly after retirement so you don’t lose that exclusion. This is a good time to map out the short-term and long-term plan for any rental properties, and see how different actions can impact the big picture.

24 Months to 18 Months Before Military Retirement

Make an appointment with your local Transition Assistance Program for required counseling.

Create a LinkedIn Account, or start building out your network.

Review and update all your military records, including educational/training records, security clearance, and administrative/personnel files. Correct anything that is wrong, and fill in any missing items. Make a copy for your own files.

Build out your three post-military budgets.

Learn about the Department of Veterans Affairs Disability Compensation application program, and plan your timeline. Identify the local organizations that offer Veterans Service Officer services. Gather reviews on the VSOs in your area, if you have more than one choice.

Start to learn about VA medical care, eligibility, and how priority groups work.

Understand the Dependency and Indemnity Compensation program. Even if you don’t expect to meet the criteria, it’s good to understand how it works.

12 Months to 18 Months Before Military Retirement

Start gathering service member and family medical records.

Create your master resume. Get help from one or more of the many resources that help veterans with resumes.

Attend a TAP workshop if you haven’t yet done so. Explore the additional add-on programs such as entrepreneurship, education, vocational training. Take your spouse, if at all possible.

Explore the various internship programs available to transitioning military members. Spouses, too!

Make sure you understand your military retirement move entitlements.

Start working on bigger medical issues, like any surgeries that you suspect you may need, or getting kids’ wisdom teeth removed.

If necessary, submit your retirement letter through your chain of command.

6 Months to 12 Months Before Military Retirement

Find out your unit or branch’s required paperwork, and timelines for the paperwork.

Start purging your household goods if you are going to be moving. Food, too.

Schedule your final medical and dental appointments.

Be sure you know when your last active duty pay will be paid, when your retirement pay will start, and when any VA disability compensation will start. No one wants to be surprised by this.

Start making more serious decisions about what life will look like after retirement. Definitely consider renting until you get settled instead of buying. Obviously, there are situations where buying makes sense. But there are a lot of times when it doesn’t.

Consider whether you would like to enroll in the Federal Long Term Care insurance program, and explore eligible family member coverage.

Consider whether you will take terminal leave or sell back your excess leave, if you have the choice. You also get 20 days of Permissive TDY for transition purposes, so factor that into the planning. (30 days if you are retiring from OCONUS.)

Review and update your will and other legal documents.

Make sure you have up-to-date civilian email and snail mail addresses on MyPay and the Thrift Savings Plan website. Set up a Department of Defense Self-Service (DS) Login, if you don’t already have one. You’ll need a DS login for all sorts of things, including Tricare, the milConnect website, and the Department of Veterans Affairs eBenefits site (which includes education benefits.)

Learn about the many veteran and spouse job programs, including:

6 Months to 3 Months Before Military Retirement

Have your Separation History and Physical Exam (SHPE). This may be multiple appointments depending on your medical history.

Submit your pre-discharge disability claim under the Benefits Delivery Discharge (BDD) program.

Create an eBenefits account. Go through the steps for a “premium” account. This will allow you to access your VA benefit information online, as well as retrieve a copy of your DD 214 whenever necessary.

Be sure that you know how to access your myPay account without using a CAC card. This includes having a Login ID and a password. You may be able to reset this information online, or you may need to have information sent to you through regular postal service mail. (That’s another reason to make sure that everyone has your correct address.)

Go ahead and download anything you need from your active duty myPay account, including old LES and tax statements. Your active duty myPay account will remain available for 13 months following retirement. When your retired pay begins, you’ll get a second menu for accessing retired pay information. Your personal information will carry over from your active duty myPay to your retiree myPay account, as should any allotments you have set up.

The Last 90 Days Before Military Retirement

Review your Pre-Separation Counseling Checklist (DD Form 2648.

Decide on your Tricare coverage, and whether you want a Tricare Supplement. Make a decision about dental and vision coverage, if desired.

Consider whether you want to utilize your Space A travel benefits during terminal leave. You’re still Category III – Active Duty, giving you a boost in getting on those flights.

Complete the VA Healthcare Registration process. You will probably need a copy of your DD214 and a form of identification. You can do this online, in person, or by mail using VA Form 10-10EZ.

Verify the information on your DD 214: be sure that your social security number, dates of service, name and other information are exactly right.

Have last medical and dental appointments for everyone in the family. Get necessary documentation, like kids’ sports physicals, to get you through the next few months.

Fill a 90 day supply of any necessary prescriptions.

About a month before your retirement, call your installation’s identification office and ask about the procedures for getting your retired military ID cards. Some installations are able to get them to you a day or two before retirement (I don’t know how – don’t ask me), and some will need you to wait until you are officially retired. Try to make appointments, if at all possible. Don’t forget that you don’t have to use the office on your installation – if that’s not convenient, or they can’t get you an appointment, use the RAPIDS appointment system to see what other options exist in your area.

The First Week After Military Retirement

Verify that your status has been updated in the Defense Enrollment Eligibility Reporting System (DEERS.) You can call a DEERS office, or check online at https://milconnect.dmdc.osd.mil/milconnect.

Get your retired identification cards.

Get multiple copies of your DD 214. Consider keeping them in separate places, just in case. Perhaps a safe deposit box, your parents’ or children’s house, etc.

Call Tricare to indicate what plan you would like to use. Arrange payments for your enrollment fees. You have to enroll in your “new” Tricare, even if you are staying with the same plan, or you won’t have coverage.

In The Months Following Military Retirement

Consider your options for your Thrift Savings Plan Account. The default recommendation from most advisors I respect is to keep it in TSP unless you have a specific need that can only be accomplished by moving it elsewhere – perhaps a Roth conversion.

Make a final decision about VGLI – the deadline to switch to VGLI from SGLI without a health examination is 120 days after retirement.

Evaluate whether you need to change your income tax withholdings to reflect your new situation. This may include changing your residence to a new state or starting a new job.

Expect to be called by representatives of the VA’s Solid Start program. They will attempt to contact you by phone several times around 90, 180, and 365 days after retirement. The purpose of this program is to ensure that every veteran knows about the benefits available through the VA.

If you did not apply for VA disability compensation through the BDD program, file your claim now (if appropriate.)

If you have any new medical conditions that arise in the year following retirement, consider whether they may be service-connected and if it would be appropriate to file a VA disability claim for them (new or updated.)

Check with your county courthouse to see if there is an option to “file” a copy of your DD-214 there. That will give you a way to get a copy even if all yours are missing, and might be faster than getting it from the VA.

In The Years Following Military Retirement

Keep DEERS updated whenever you have a life change, including marriage, divorce, birth of a child, child marrying or aging out of military dependency, moves, becoming eligible for Medicare, or death of the sponsor a family member.

Dependent children may remain on your Tricare coverage until age 21, or age 23 if they are a full-time student and you provide the necessary documentation to the DEERS office. Once they age off Tricare, they may continue coverage by purchasing Tricare Young Adult coverage.

If you receive extra VA disability compensation because you have children, you will need to provide the appropriate documentation once they turn 18. You can continue to receive extra benefits for them until they turn 23 as long as they are in school full-time. This extra benefit applies if your VA disability rating is 30% or more. However, keep in mind that you generally can’t receive extra payments for your children and have them also receive VA education benefits. Make sure that’s all sorted out correctly each year.

Keep DFAS informed of changes to your address, phone number and email address. Notify DFAS if you have a life change such as a marriage, divorce, birth of children, or deaths. This includes contact information for your beneficiaries, such as for Arrears of Pay or Survivor Benefit Plan.

At some point, you or your spouse may need hearing aids. If you’re not eligible to have them covered by the VA, look into the Retiree At-Cost Hearing Aid program.

Keep in the back of your head the 1 year deadline for adding SBP coverage for new dependents: a new spouse, a new child, a former spouse. There are specific eligibility rules for each of these situations, but the important thing to remember is that you only have one year

If you need to file a secondary claim for conditions that are caused or aggravated by a service-connected disability, consider using the Decision Ready Claims program.

When You Turn 65

When you become eligible for Medicare, typically at age 65, your Tricare coverage will transition to Tricare for Life. You must sign up for Tricare Part A and B to have Tricare for Life coverage.

Retirement is a whirlwind of things to do, mixed in with excitement and anxiety and fun and stress. Use this list to help you make sure that everything gets done as easily as possible, so you can focus on the good parts!

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