Preparing to Retire or Separate

The transition timeline

The single biggest mistake is starting late. If you're retiring, begin the Transition Assistance Program (TAP) 18–24 months out. For separation, the critical window opens around 180 days. Here's the order that protects you.

12–18 months out (retirement) / as early as possible

• Start TAP; attend the benefits, financial, and (if retiring) SBP and retirement briefings.
• Begin documenting every medical and dental issue in your records — this is the foundation of your VA claim.
• Consider DoD SkillBridge if you want a civilian-industry internship during your final months.

90–180 days out

• File your VA claim through BDD (Benefits Delivery at Discharge) — the window is 180 to 90 days before separation.
• Schedule your Separation History and Physical Examination (SHPE), 90–180 days out.
• Request terminal leave, and house-hunting/job-hunting leave if authorized.
• Map your healthcare handoff (TAMP, CHCBP, retiree TRICARE, employer, or VA) — see the next section.
• Request copies of medical and dental records (can take weeks to months).

The final weeks

• Review your draft DD-214 before you sign — name, SSN, dates, awards, schools, and the RE code. Errors are painful to fix later.
• Zero out your Government Travel Card — a delinquency at separation can be reported to credit bureaus and even threaten a clearance.
• Complete the TAP capstone and get the completion certificate.
• Arrange your final household-goods move with transportation.

Healthcare: the cliff

This is where transitions go wrong. For most separating members, active-duty TRICARE ends the day you separate — there is no grace period. Map the handoff before you out-process.

If you're separating (not retiring)

• TAMP — the Transitional Assistance Management Program gives 180 days of TRICARE-equivalent coverage, but only if you qualify (generally involuntary separations, post-contingency, and certain conditions). It is not automatic and not for everyone — verify eligibility with your personnel office.
• CHCBP — if you don't qualify for TAMP, the Continued Health Care Benefit Program is a purchasable bridge, like COBRA, for 18–36 months. You pay a premium, but it prevents a gap.
• Employer or Marketplace — ideally line up employer coverage to start the day after separation, or use the Health Insurance Marketplace.
• VA health care — many veterans qualify based on service; service-connected conditions are treated at priority, and a 10%+ rating means no-cost care for those conditions.

If you're retiring

• Retiring disenrolls you from active-duty TRICARE Prime. Official rule You must actively enroll in a retiree TRICARE plan (Prime or Select) within 90 days of retirement, or you lose coverage (retroactive enrollment may be possible within 12 months). Retiree plans may carry enrollment fees.
• Dental and vision don't continue automatically — enroll in the FEDVIP program (there are enrollment windows after retirement).

Life insurance: SGLI → VGLI

Your low-cost SGLI doesn't follow you out. You have a window to replace it — and a decision to make about whether VGLI or private term is the better long-term fit.

• Official rule SGLI continues free for 120 days after separation.
• VGLI (Veterans' Group Life Insurance) lets you convert up to $500,000 with no medical exam if you apply within 240 days of separation. You can still apply later (up to one year and 120 days after discharge) but may have to answer health questions.
• The catch: VGLI premiums rise with age, so for a young, healthy veteran a private level-term policy is often cheaper for the same coverage over the long haul. If you have any health concerns, the no-exam VGLI window is valuable — don't let it lapse.
• Family coverage (FSGLI) for a spouse/children cannot be converted to VGLI — plan separate coverage (employer or private) for them.

The Survivor Benefit Plan (SBP)

SBP is one of the few truly irreversible decisions in your transition, and it's for retirees (20+ years or a qualifying medical retirement). Take the time to understand it.

• Official rule SBP pays a surviving spouse or eligible beneficiary up to 55% of your retired pay for life if you die.
• It's elected at retirement, your spouse must consent in writing to anything less than full coverage, and the decision is generally irrevocable.
• Premiums are 6.5% of the base amount you elect, deducted from retired pay.
• StandWatch guidance SBP's real strength is that it's guaranteed, inflation-protected income your survivor cannot outlive — something a lump-sum life-insurance policy can't easily replicate. Whether it's right depends on your spouse's age and income, your health, and the other insurance and assets you hold. Many families use a mix. Read the official SBP materials and talk to a counselor before you sign.

The VA disability claim

Your VA claim can shape your finances and healthcare for the rest of your life. The two rules that matter most: file early and document everything.

• File through BDD (Benefits Delivery at Discharge) 180 to 90 days before you separate. It's built to get you a rating around your separation date instead of waiting months.
• Schedule your SHPE (Separation History and Physical Examination) 90–180 days out — DoD and VA use it as a single separation exam capturing your full medical history.
• Document every condition in your records before you leave. Describe honestly how symptoms affect you on your worst days, not only your best — the rating reflects how a condition actually affects you.
• Get copies of your complete medical and dental records — and a final copy after any care that happened after you filed.
• Use a VSO. Accredited Veterans Service Officers help you file at no charge — be cautious of anyone charging large fees to "maximize" a claim.

Pay, TSP & taxes

Your income structure changes the day you leave. A little planning prevents a cash crunch and an April surprise.

Final pay & terminal leave

• BAH and BAS stop on your separation date. Build a cash reserve to bridge the gap until your first civilian paycheck or your retired pay/VA compensation starts.
• Terminal leave: you can take accrued leave as paid time at the end (staying on active pay/benefits) or, in some cases, sell leave — the math differs, and sold leave is taxed. Confirm the computation with finance.
• Make sure DFAS has correct info so final pay and (for retirees) retirement pay start on time.

TSP

• You don't have to move it — you can leave funds in the TSP's low-cost funds, or roll to an IRA for more investment options.
• Official rule A direct trustee-to-trustee rollover has no time limit; an indirect rollover (where TSP sends you a check) must be redeposited within 60 days or it's taxed (and possibly penalized).
• If you have combat-zone tax-exempt contributions, get the tax treatment right before you roll anything — those dollars have special handling.

Taxes on retired pay

• Military retired pay is taxable federally, but many states exempt it (fully or partially). If you're choosing where to settle, state tax treatment of military retirement can be worth real money.
• VA disability compensation is not taxed.

The DD-214 & final out-processing

The DD-214 is the single most important document you'll leave with — it's your proof of service for VA benefits, employment, home loans, and burial. Get it right.

• Review the draft before you sign. Check name, SSN, dates, rank, awards, schools, and especially the RE (reentry) code and character of service — these affect future benefits and employment.
• Get multiple certified copies and store originals somewhere safe (and a scan somewhere secure). You'll need it for years.
• Clear every station — medical, dental, finance, supply, security, command — and confirm your travel voucher and final-move paperwork are submitted.
• Confirm your post-service address in DEERS so TRICARE/TAMP and VA correspondence reach you.

Retirement & Separation FAQ

Sources & where to verify

• Military OneSource — transition, TAP, and benefits help. militaryonesource.mil (accessed July 2026).
• TRICARE — retiring, TAMP, and enrollment deadlines. tricare.mil (accessed July 2026).
• VA — disability claims (BDD), health care, and benefits. va.gov (accessed July 2026).
• DFAS — final pay, retired pay, and SBP. dfas.mil (accessed July 2026).
• VA life insurance (VGLI) — conversion and deadlines. va.gov/life-insurance (accessed July 2026).
• Your transition office, DFAS, VA, and an accredited VSO — the authoritative sources for your specific dates and amounts.

Recent updates

• July 1, 2026 — Added an interactive SBP premium and survivor-annuity quick calculator.
• July 1, 2026 — Guide published: transition timeline, healthcare handoff (TAMP/CHCBP/retiree TRICARE), SGLI→VGLI, SBP, the VA/BDD claim, TSP and taxes, and the DD-214.