Military Separation Checklist: Your Final 12 Months

Transition · Updated July 2026 · 14 min read

Your last year in uniform runs on a set of fixed deadlines, and several of them close quietly. This checklist walks through what has to happen and when, from the 365-day mark to the day your DD214 is signed.

The 12-month mark: start TAP and map the whole year

The Transition Assistance Program (TAP) is not optional. Pre-separation counseling must start no later than 365 days before you transition, and TAP is mandatory for separating service members who have served 180 continuous days or more on active duty. That 365-day figure is a legal floor, not a recommendation. Military OneSource advises retiring service members to begin the process at least two years before retirement, because the useful parts of the year get crowded fast.

TAP begins with individualized initial counseling, a personal self-assessment, and an Individual Transition Plan (ITP) — the written plan that maps your goals, gaps, and deadlines. Your ITP drives everything else, so treat it as a working document rather than a form to sign. The program includes pre-separation counseling, a Department of Defense transition day covering managing your transition, translating military skills into civilian terms, and financial planning, a VA benefits briefing, and Employment Fundamentals of Career Transition delivered by the Department of Labor. On top of that core, you complete at least one elective track: employment, vocational training, education, or entrepreneurship.

Two hard dates sit at the back end of TAP. Your capstone event, where your commander verifies you have met the Career Readiness Standards, must happen no later than 90 days before separation or release from active duty. Your mandatory final medical and dental exams, including the separation health assessment, must also happen no later than 90 days before you separate. Both are prerequisites for things that come later, which is why a 90-day cushion matters more than it looks.

If your separation is unanticipated, or you are a Reserve component member demobilizing on short notice, TAP must begin as soon as possible within whatever time remains. Shortened timelines do not remove the requirement; they compress it. Tell your transition counselor immediately if your date moves.

Bring your spouse. Military OneSource states that caregivers and spouses are especially encouraged to attend pre-separation counseling with their service member, and most of the decisions in this checklist are household decisions.

• Pre-separation counseling: must start no later than 365 days before transition
• Capstone event: no later than 90 days before separation
• Final medical and dental exams: no later than 90 days before separation
• Retiring? Military OneSource says begin at least two years out
• Spouses and caregivers are especially encouraged to attend pre-separation counseling

SkillBridge, terminal leave, and permissive TDY all compete for the same days

DoD SkillBridge lets you spend your last stretch of service training or interning at a civilian organization while still on active duty, drawing military pay and benefits. Military OneSource states that service members can receive up to 180 days of permissive duty with approval from their unit commander, used during the last 180 days of military service. The employer provides training and experience; SkillBridge itself carries no obligation for anyone to hire you at the end, and treating it as a guaranteed job offer is a common and costly mistake.

This is the area most likely to have changed since anything you last read. Across 2024 and 2025 the services tightened SkillBridge considerably, adding caps on program length that vary by rank and pushing approval authority to higher levels of command. The Army did this through MILPER Message 25-116, issued 3 April 2025, which superseded MILPER 24-486; the Air Force, Space Force, Navy, and Marine Corps issue their own SkillBridge instructions. Army MILPER messages carry expiration dates and get superseded, so by mid-2026 the governing document may well be a newer one. Do not assume you will get the full 180 days, and do not plan around a policy you have not confirmed with your own career counselor this month.

Terminal leave is separate from SkillBridge and comes out of leave you have actually earned. By statute, members accrue leave at 2.5 calendar days for each month of active service — 30 days a year — and generally may not accumulate more than 60 days, though narrow special leave accrual rules allow more in specific deployment and missing-status situations. Selling leave back is capped at 60 days across an entire career, with limited statutory exceptions, and the payment is calculated on basic pay only. Because sell-back excludes allowances like housing and subsistence, taking terminal leave is usually worth more than selling it, though your circumstances and tax situation decide that.

Permissive TDY (permissive temporary duty, or PTDY) for job hunting and house hunting is a third bucket. The number of days authorized, and whether you qualify at all, varies by branch, by whether you are retiring or separating, and by whether you are stationed stateside or overseas — and approval sits with your commander. Because the rules are service-specific and change, get the current figure from your personnel office rather than from a forum post. The scheduling point is the one that matters: SkillBridge, terminal leave, and PTDY all draw down the same final months. Put them on one calendar early, because they cannot all be taken at full length.

Months 6 to 3: file your VA disability claim inside the BDD window

Benefits Delivery at Discharge (BDD) is the single most time-sensitive item in this checklist. BDD lets you file a VA disability compensation claim before you leave so that VA can begin processing while you are still in uniform, which shortens the wait for a decision after separation. VA sets the filing window at between 180 and 90 days before you leave the military. It is a window with a floor and a ceiling: file earlier than 180 days out and you are too early, and once you are inside 90 days you can no longer use BDD at all.

Missing the BDD window does not mean missing your chance to claim. If you have fewer than 90 days remaining, VA states you can still file a standard pre-discharge disability claim before you separate from active duty. You simply lose the expedited BDD handling. Separately, submitting an intent to file gives you up to one year to complete and submit the claim while protecting a potential earlier effective date for back pay — and VA notes that if you file for disability compensation online you do not need to submit a separate intent to file, because your effective date is set automatically when you start filling out the form, before you submit it.

BDD carries conditions. You must be available to go to VA exams within 45 days of the date you submitted your claim, so do not file BDD and then disappear on terminal leave or a SkillBridge assignment three time zones away without planning for it. You will also need a completed Separation Health Assessment Part A self-assessment. Certain claims are excluded from BDD and go through the standard pre-discharge process instead: claims needing case management for a serious injury or illness, terminal illness, cases where you are waiting to be discharged while hospitalized at a VA or military treatment facility, cases awaiting a character of discharge determination, and cases where you cannot attend a VA exam during the 45-day window.

You should not pay anyone to file this. VA states that the services an accredited Veterans Service Organization (VSO) representative provides on your VA benefit claims are always free. VA also states that an accredited attorney or claims agent can charge you fees for their services, which is legitimate for appeals and complex work, but no one needs to pay for basic help preparing an initial claim. County Veterans Service Officers are another free, accredited option and are often the fastest way to get someone sitting across a desk from you.

Get your medical and dental records in your own hands

Your service treatment records are the evidence base for every disability claim you will ever file, including ones you have not thought of yet. Do not assume the records will be there when you need them, and do not assume someone else is keeping a copy for you. Request complete copies of your medical and dental records before you separate, while you still have access to the military hospital or clinic that holds them, and store them somewhere you control.

How you retrieve records depends on when you served. TRICARE states that paper copies of service treatment records were digitized after retirement or separation for those who retired or separated after January 1, 2014. You can request records in person at your last military hospital or clinic, through the MHS GENESIS Patient Portal (the Military Health System's online patient portal) if you receive care at a military facility, or by completing Standard Form 180, Request Pertaining to Military Records, and sending it to the address listed on the form for your branch and separation date. milConnect, the Defense Department's self-service records portal, covers Air Force members discharged after October 1, 2004, Army after October 1, 2002, Marines after January 1, 1999, and Navy after January 1, 1995. Anyone outside those windows goes through the National Archives.

The quiet failure mode here is the undocumented condition. If your knees, back, hearing, or sleep have been a problem for years but you handled it without going to sick call, there may be nothing in your record establishing that it began in service. Your final separation health assessment is the last clean opportunity to get current conditions written down by a military provider. Report everything honestly, including things you have learned to work around. Understating symptoms at the exit exam is one of the most common regrets veterans describe later.

Finally, read your DD214 — the Certificate of Release or Discharge from Active Duty — carefully before you sign it. It drives unemployment claims, VA eligibility, education benefits, and federal hiring for the rest of your life, and correcting an error afterward is far harder than catching it at the desk. Keep multiple certified copies, and store a digital copy somewhere you will still be able to reach in ten years.

Health coverage: the gap most people do not see coming

The most widespread misconception about separating is that everyone gets 180 days of free transitional TRICARE. They do not. The Transitional Assistance Management Program (TAMP) provides 180 days of health care benefits after regular TRICARE benefits end, with no premiums, but only to specific categories. TRICARE lists them as: members involuntarily separated from active duty under honorable conditions (including those receiving voluntary separation incentive or voluntary separation pay, if they do not receive retired or retainer pay); National Guard and Reserve members separating from active duty of more than 30 consecutive days in support of a contingency operation or a preplanned mission; National Guard members separating from more than 30 consecutive days of Title 32 orders supporting a national disaster response; members separating after involuntary retention (stop-loss) in support of a contingency operation; members separating after voluntarily agreeing to stay on active duty for less than one year in support of a contingency operation; members with a sole survivorship discharge; and regular active duty members who agree to become members of the Selected Reserve. A routine end-of-enlistment separation that fits none of these categories does not qualify. Confirm your status rather than assuming it.

If you are retiring, the deadline is different and it is strict. TRICARE states you have 90 days after your retirement date to enroll in a TRICARE health plan. Miss it and you lose automatic coverage, leaving you eligible for care at a military hospital or clinic only if space is available — meaning you are seen only when capacity allows, after enrolled patients. There is a recovery path: you can request retroactive enrollment up to 12 months from retirement, but enrollment fees have to be paid back to the retirement date, and after that window you are waiting for TRICARE Open Season or a qualifying life event. Update your address and information in the Defense Enrollment Eligibility Reporting System (DEERS), the database that controls your and your family's eligibility, as soon as you have orders.

The Continued Health Care Benefit Program (CHCBP) is the bridge if nothing else covers you, and it is a real cost you should budget for now. You can enroll within 60 days of losing your eligibility for TRICARE, which includes losing TAMP coverage, and your separation must be under other than adverse conditions. Separating service members can buy up to 18 months of coverage; certain dependents and unremarried former spouses can get up to 36 months. TRICARE's current cost table lists calendar year 2026 premiums of $2,103 per quarter for individual coverage and $5,339 per quarter for family coverage. Those figures are set annually, so check the current table before you budget. Compare CHCBP against an employer plan and the Affordable Care Act (ACA) marketplace before defaulting to it.

Two more items close on their own schedule. Your Servicemembers' Group Life Insurance (SGLI) can convert to Veterans' Group Life Insurance (VGLI). VA states you can sign up for VGLI coverage up to the amount you had through SGLI — the program's overall ceiling is $500,000, but your starting VGLI amount is capped at the SGLI you actually carried. If you sign up within 240 days of leaving the military you will not need to prove you are in good health. You can still apply up to 1 year and 120 days after leaving, but after the 240-day mark you must submit evidence that you are in good health — and if your health has changed, that is not a formality. Separately, apply for VA health care right away. If you served in a theater of combat operations after November 11, 1998 and were discharged or released on or after September 11, 2001, you get 10 years of enhanced eligibility from your discharge date, which places you in priority group 6 or higher. For those who enlisted after September 7, 1980 or entered active duty after October 16, 1981, the general minimum duty requirement is 24 continuous months of active duty or the full period for which you were called, with exceptions including discharge for a service-connected disability, hardship, or early out. A dishonorable discharge bars eligibility; an other-than-honorable or bad conduct discharge may still allow benefits after a Character of Discharge review.

• TAMP: 180 days, premium-free — but only for the specific separation categories TRICARE lists
• Retirees: enroll in a TRICARE plan within 90 days of your retirement date
• CHCBP: enroll within 60 days of losing TRICARE eligibility, separation must be under other than adverse conditions
• VGLI: apply within 240 days to skip the health review; absolute deadline is 1 year and 120 days
• VGLI starting coverage is capped at the SGLI amount you carried, not automatically $500,000

Relocation, household goods, and financial runway

Military OneSource states you have one year after leaving active duty to complete your final move. That sounds generous until you factor in that storage entitlements, extension rules, and the details of what the government will pay for differ between retirees and separatees, and have been revised in recent Joint Travel Regulations updates. Because those rules are genuinely different depending on your category and are subject to change, book time with your installation's personal property or transportation office early rather than relying on secondhand figures. Ask specifically about how long you have, what storage you are entitled to, and what happens if you exceed it — unclaimed storage costs land on you personally.

Build a cash buffer, and build it larger than feels necessary. Your final pay is not a single clean deposit: terminal leave pay, any sell-back, travel settlements, and final allowances arrive on different schedules, and lump-sum leave payments are taxable income. Meanwhile, civilian pay usually starts weeks after you begin work. Plan for the gap between your last military paycheck and your first civilian one, and do not count on any specific timing.

Unemployment Compensation for Ex-servicemembers (UCX) exists for exactly this gap, and it is underused because people assume it is not for them. The Department of Labor states you must have been separated under honorable conditions. Under federal law at 5 U.S.C. 8521, qualifying service generally also means you completed the first full term of active service you initially agreed to serve — but the statute lists exceptions that still qualify, including early release for the convenience of the Government, medical disqualification, pregnancy or parenthood, a service-incurred injury or disability, and hardship (including a sole survivorship discharge). For reservists, active duty in a reserve status counts only if it was a continuous period of 180 days or more. If you were released early, do not assume you are out — check. Benefits are administered by states: the Department of Labor states that the law of the state under which the claim is filed determines benefit amounts, the number of weeks benefits can be paid, and other eligibility conditions. Have your DD214 in hand when you file. The program is implemented under federal regulations at 20 CFR Part 614.

One planning point that catches nearly everyone: your military compensation includes allowances such as housing and subsistence that are not taxed. A civilian salary is taxed in full. That means matching your current base pay with an equivalent gross salary will leave you worse off, sometimes substantially. Work out your actual total compensation, including the value of those allowances and your health coverage, before you evaluate any civilian offer.

Start the job search at 12 months, not at three

The most common regret in transition is starting the job search too late. Hiring cycles for the roles most veterans want run long, and applications submitted from a position of financial pressure tend to produce worse outcomes than ones submitted with nine months of runway. Begin building your résumé, your professional network, and your target list of employers at the 12-month mark, alongside TAP rather than after it.

Translation is the practical work. Your MOS (Military Occupational Specialty), rating, or AFSC (Air Force Specialty Code) does not mean anything to most civilian hiring managers, and neither do your award citations. TAP includes a military-to-civilian skills crosswalk for exactly this reason. Rewrite your experience in terms of outcomes, scope, budget, and people managed. If you hold a security clearance, understand its currency rules and state its status accurately, because for many employers it is the single most valuable line on your résumé.

Education benefits interact with your job search timing, so know where you stand before you decide. VA states that if your service ended on or after January 1, 2013, your Post-9/11 GI Bill (Chapter 33) benefits will not expire. If your service ended before January 1, 2013, those benefits expire 15 years after your last separation date from active service. That difference should shape whether you go to work immediately, go to school, or do both.

Use the free infrastructure. The Department of Labor's Employment Fundamentals of Career Transition workshop is part of TAP, and American Job Centers and state workforce agencies provide no-cost help with résumés, interviewing, and job placement. Accredited Veterans Service Organizations and County Veterans Service Officers can help you sort benefits questions in parallel. There is a large paid industry selling transition services; nearly everything essential in this checklist is available at no cost from an accredited or government source.

Sources

Every figure above is drawn from these official sources. Benefit rates and thresholds change — check the current official page before you act.

• Military OneSource — About the DoD Transition Assistance Program
• Military OneSource — DoD SkillBridge Program
• DoD SkillBridge — Official program site
• U.S. Army — Army revises rules for participation in civilian transition job-training programs (MILPER 25-116)
• VA — Pre-discharge disability claims (BDD)
• VA — How to file a VA disability claim
• VA — Your intent to file a VA claim
• VA — Get help filing your claim
• VA — Eligibility for VA health care
• VA — Veterans' Group Life Insurance (VGLI)
• VA — Post-9/11 GI Bill (Chapter 33)
• VA — Request your military service records (including DD214)
• TRICARE — Transitional Assistance Management Program (TAMP)
• TRICARE — Continued Health Care Benefit Program (CHCBP)
• TRICARE — CHCBP costs
• TRICARE — Retiring
• TRICARE — My Military Health Records
• U.S. Department of Labor — Unemployment Compensation for Ex-servicemembers (UCX)
• U.S. Department of Labor VETS — Employment Fundamentals of Career Transition (EFCT)
• 5 U.S.C. § 8521 — UCX definitions (Federal service)
• 20 CFR Part 614 — Unemployment Compensation for Ex-servicemembers
• 10 U.S.C. § 701 — Leave accrual and accumulation
• 37 U.S.C. § 501 — Payment for accrued leave
• National Archives — Veterans' Service Records