Military transition checklist: 3 years out to your first year out

Paperwork and family readiness

Start early. These steps take time

• Get your legal papers in order: Legal Papers Every Adult Should Set Up Now.
• Decide about transferring your Post-9/11 GI Bill to family. VA says you need at least 6 years of service on the date your request is approved, and 4 more years of service. The person receiving it must be in DEERS. You request it through milConnect while you are on active duty. The Defense Department decides whether it is approved (VA: transfer your benefits).
• Know where your records are and how to get your DD-214: Get Your DD-214 and Military Records.
• Read the whole path once: Plan Your Transition.

Start the Transition Assistance Program

DoD instruction 1332.35, as summarized on the Air Force benefits site

• Start TAP no later than 365 days before you separate. The Air Force page recommends starting up to 18 months out if you are separating and up to two years out if you are retiring.
• Complete the Pre-Separation Brief at least 365 days before you separate. If you have less than 365 days left, start as soon as possible.
• TAP includes a mandatory DoD Transition Day, VA Benefits and Services, and a Department of Labor employment course (some exemptions). Your Individual Transition Plan decides which two-day track you take.
• Soldiers: look at civilian credentials your Army job matches and what the Army will pay for: Army Pays for Your Civilian Credential.

Free tools and mentoring for your job search

Each program's own page, checked October 20, 2026. Offers can change

• ChatGPT Plus, free for a year. OpenAI says U.S. servicemembers and veterans within 12 months of retirement or separation can claim a free year of ChatGPT Plus. Eligibility is verified through SheerID. OpenAI's page does not say what happens after the free year or how to cancel, so check before you claim (OpenAI: ChatGPT for veterans, claim page: chatgpt.com/veterans-claim).
• LinkedIn Premium, free for 12 months. LinkedIn says this is a one-time offer that lasts 12 months once redeemed, and you must not already have Premium. It is given out through nonprofit partners, so you must take part in career services from Hire Heroes USA, Student Veterans of America or Hiring Our Heroes. LinkedIn says its partners decide who is eligible (LinkedIn: military and veterans).
• Coursera, free for 12 months. Veterans Transition Support (VTS) says it offers 12 months of free Coursera certificates and specializations to veterans, active duty, reservists, National Guard and military spouses. You register on VTS's Eventbrite page, then VTS confirms eligibility and sends your access link. VTS says there is no deadline (VTS: free Coursera).
• ACP, a free one-year mentor. American Corporate Partners says its programs are free for transitioning service members, veterans and active-duty spouses. You apply online, and it matches you with a volunteer mentor (ACP, apply: apply.acp-usa.org/protege).
• MilMentor, free mentoring. Its site says it pairs service members, veterans and military spouses with more than 1,000 mentors at employers, and that it is free. The site does not say how to sign up (milmentor.com).
• Hire Heroes USA, free career coaching. Its site says it offers one-on-one career coaching, resume reviews, interview preparation and job board access at no cost to transitioning service members, veterans and military spouses. You register on its site (hireheroesusa.org). This is also one of the partners for the LinkedIn Premium offer above.
• Onward to Opportunity (Syracuse University's IVMF), certification training. IVMF says access to the program is free for service members, veterans and military spouses. It includes a 20 to 30 hour prep course for one of more than 40 certifications, plus resume help and career coaching. Exam fees are covered for one certification only if you enroll during your transition from active duty or you are an unemployed veteran or military spouse. Everyone else pays their own exam, which IVMF says can cost up to $1,500. IVMF's page does not show the full eligibility criteria or current start dates (IVMF: O2O).
• A free job coach at an American Job Center. See Free One-on-One Job Coaching for Veterans (DVOP).
• Candorful, live mock interviews. Candorful says it connects transitioning service members, veterans and military spouses with interview coaches for live practice interviews. Its site does not say what it costs, so ask before you book (candorful.org).

File your VA claim and line up training

Dates that depend on your separation date

• If you qualify, file your VA disability claim 180 to 90 days before you separate: Benefits Delivery at Discharge (BDD).
• If your service allows it, look at SkillBridge for your last 180 days: SkillBridge: Ten Free Programs and the Questions to Ask.
• Finish your Capstone. It should be done no earlier than 12 months and no later than 90 days before you separate.
• Check what your family needs while you are still in: TRICARE: The Plans and Who Qualifies.

Before your last day

What to get in your hands

• Get your DD-214 and keep copies: Get Your DD-214 and Military Records.
• Understand your 180 days of TRICARE coverage after your regular benefits end, with no premiums: TRICARE TAMP.
• Decide about Veterans Group Life Insurance (VGLI). VA says you can apply without answering health questions within 240 days after you separate. You can still apply up to 1 year and 120 days after you separate, but you must show proof of good health. Your SGLI coverage ends 120 days after you separate. The first VGLI amount equals the SGLI amount you have when you separate, so do not cancel SGLI before you leave (VA: apply for VGLI)

If you are retiring

Retirement only

• Enroll in TRICARE within 90 days after your retirement date. If you miss it, you can request retroactive enrollment within 12 months of your retirement date, but claims are not paid until enrollment is complete (TRICARE: retiring).
• Understand your retirement pay system: Blended Retirement System.
• If you are retired and have a VA rating, read CRDP: retired pay and VA disability.
• Read Six Benefits Retirees Miss.
• Get Survivor Benefit Plan (SBP) counseling from your installation Retirement Services Officer before you retire. You make your SBP election on DD Form 2656. The Air Force benefits page says an election that gives your spouse less than the maximum allowed by law needs your spouse's written, notarized concurrence, and that the spouse premium is 6.5 percent of the base amount (Air Force benefits: Survivor Benefit Plan). That page does not state a pre-retirement deadline, so ask your Retirement Services Officer.

After you separate

The first 90 days and the year after

• Expect VA Solid Start to try to contact you three times: days 0 to 90, days 91 to 180 and days 181 to 365. VA Solid Start: VA calls you in your first year.
• If you were not able to file before you left, file your VA claim now: Plan Your VA Claim.
• Military OneSource says it supports separating and retiring service members and their immediate family for 365 days after separation or retirement, with help on careers, moving, finances and tax filing (including MilTax). Call 800-342-9647 (Military OneSource: a full year of support). Its article is dated April 21, 2022 and does not state a cost, so confirm on its current site.
• If you are out of work, read Unemployment Pay After Service (UCX).
• If you want help with training or a job, read Veteran Readiness & Employment (VR&E).

What I could not verify

• I read the TAP timing from the Air Force benefits site, which cites DoD Instruction 1332.35. I did not read the instruction itself. Your branch may set its own dates, so ask your TAP counselor.
• The VGLI numbers come from VA's current VGLI page. VA's page implies you need SGLI when you separate, but it does not state it as a rule.
• The SBP details come from the Air Force benefits page. It does not cite a regulation or state a pre-retirement deadline, so I did not give one. Ask your Retirement Services Officer.
• The Army credential item applies to Soldiers only. I did not check the other branches' programs.
• For the free career tools, I read each program's own page. I could not read LinkedIn's help page, so the LinkedIn terms come from its program page. ACP's site does not list its eligibility criteria. ACT NOW Education's site did not confirm the details of its own academy program, so I left it out.
• The Military OneSource details come from a 2022 article. I did not confirm Microsoft's MSSA training program, because I could not read its page. I did not include Hiring Our Heroes' SkillBridge fellowship, because the only page I found was a 2025 flyer.