Separating or Retiring From Service: Your First-Year Benefits Timeline

Last verified: October 2026 · Part of our "Benefits by Life Situation" series

Disclaimer: This guide is general information, not legal or financial advice, and it is not advice about any VA claim. We are an independent site and are not affiliated with, endorsed by, or operated by the U.S. Department of Veterans Affairs (VA) or the Department of Defense. Rules change. Always confirm with the official source linked next to each fact.

The short version

Leaving the military starts several clocks at once. Some deadlines can't be undone if you miss them. This guide puts them on one page, then walks through health care, life insurance and the first-year checklist.

⏰ Your deadline table

Part 1: Before you separate

The DoD transition timeline

DoD's Managing Your Transition Timeline lays out tasks starting well before your separation date (DoD TAP: Managing Your Transition Timeline). Use it alongside this guide.

The BDD window: what it is (general information only)

VA's Benefits Delivery at Discharge program lets you file a disability claim 180 to 90 days before you leave. Per VA, you must (VA: pre-discharge claim; VBA: BDD program):

• Be on full-time active duty (including Guard, Reserve or Coast Guard on active duty) with a known separation date
• Be available for VA exams within 45 days of filing
• Include the Separation Health Assessment, Part A Self-Assessment

VA says BDD's goal is a decision within 30 days after separation (VBA page).

We don't give claim advice. VA notes you can file "online or with the help of a VA accredited representative." Free help from a VSO is described under "Get individual help" below.

Related: a pre-discharge claim affects the VA home loan funding fee only if you get a proposed or memorandum rating before closing. See Guide 2: Buying a Home .

Transfer your GI Bill (if you plan to)

VA: "While you're still on active duty, you'll need to request a Transfer of Education Benefits (TEB) from the DOD through milConnect" (VA). Details are in Guide 3: Kids, Spouse & College .

Get your records in order

• DD-214: the National Archives provides free copies to veterans and next of kin, and it warns that some companies charge for this free service (National Archives).
• VA letters: once you're in VA's system, you can download benefit letters online (VA letters).

Part 2: Health care after you separate

VA health care: apply early

VA says you can apply "as soon as you've received your separation or retirement papers," and you'll be enrolled once you've separated (VA: active-duty and VA health care). VA also says a member of its Concierge for Care team will call you soon after you separate (same page).

Toxic exposure (PACT Act): VA says, "All Veterans who meet basic service and discharge requirements and who were exposed to toxins and other hazards while serving our country—at home or abroad—are now eligible for VA health care" (VA: health care eligibility).

Combat veterans: the 10-year enhanced eligibility period

VA's web pages give differing discharge dates for this benefit, so check with VA before you rely on any one date.

• What the statute says: under federal law, a veteran who served in a theater of combat operations after November 11, 1998, and was discharged or released after September 11, 2001, has enhanced VA health care eligibility for the 10-year period beginning on the date of discharge or release (38 U.S.C. 1710(e)(3), as amended by the PACT Act). The law also set a one-year enrollment period starting October 1, 2022, for certain veterans discharged between September 11, 2001 and October 1, 2013 who had not enrolled (same source).
• VA's active-duty page lists a discharge date "on or after January 29, 2003" and refers to OEF, OIF and OND service (VA).
• VA's priority groups page lists discharge "on or after October 1, 2013" in one place and "on or after September 11, 2001" in another, each with 10 years of enhanced eligibility (VA).

What to do: confirm your own dates with VA's health benefits hotline at 877-222-8387 or with an accredited VSO. VA's advice is the same on every page: "we encourage you to apply for VA health care right away" (VA).

VA dental: a 180-day window

VA says you may be eligible for one-time dental care: "Be sure to apply within 180 days of discharge or separation" (VA).

TRICARE

• Retirees: "You'll need to enroll within 90 days after your retirement date even if you're already enrolled in TRICARE on active duty."
• Guard and Reserve: "You'll have 90 days from your separation date to change your health plan."
• Source for both: VA: active-duty and VA health care, which links to TRICARE for details.

Part 3: Life insurance: SGLI to VGLI

Per VA (VGLI; apply for VGLI):

• SGLI coverage ends 120 days after separation.
• VGLI lets you keep group coverage, up to $500,000. Your starting amount equals your SGLI at separation, so VA advises not cancelling SGLI before you separate.
• No health questions if you apply within 240 days.
• Final deadline: 1 year and 120 days after separation.

VA describes VGLI as useful "transition insurance" while you shop for another policy, to avoid a gap in coverage (VA).

Part 4: Support that's time-limited

Military OneSource is available to veterans and immediate family for 365 days after separation, retirement or discharge. After that, VA is the main resource (Military OneSource eligibility).

✅ First-year checklist

• ☐ Put every date from the deadline table on your calendar
• ☐ Get your DD-214 copy (National Archives)
• ☐ Apply for VA health care (VA)
• ☐ Decide on VGLI before day 240
• ☐ Retirees: enroll in TRICARE within 90 days
• ☐ Apply for possible VA dental care within 180 days
• ☐ Set up a VA.gov account and update your address (VA)
• ☐ Moving? See Guide 1
• ☐ Get claim help only from an accredited representative (below)

Get individual help (free, accredited)

This guide is general information. For help with anything about your own VA benefits or claims, talk to someone accredited by VA.

• Find a VA-accredited representative or Veterans Service Organization (VSO). VSO representatives help for free. VA's official page explains your options and links to its accreditation search (VA: get help from an accredited representative or VSO).
• Check that anyone helping you is accredited. VA's Office of General Counsel explains that without accreditation, a person "may not independently assist claimants in the preparation, presentation, and prosecution of claims for VA benefits" (VA OGC: Accreditation FAQs).
• Your state's veterans affairs department (directory via NASDVA) can explain state benefits and point you to local help.

We do not help with VA claims, ratings or appeals, and we never charge veterans for information. If someone offers paid claim help, check their accreditation first.

Keep going

• Guide 1: Moving to a New State
• Guide 2: Buying a Home : funding fee timing with pre-discharge claims
• Guide 3: Kids, Spouse & College : GI Bill transfer
• Guide 5: Turning 65 / Aging
• State Benefit Change Tracker

Last verified: October 2026. Found something out of date? Tell us (placeholder).