The Transition Timeline — What To Do, Counted From Your Separation Date
Most transition checklists are a flat list, which is useless — the only thing that matters is what's due now, measured from your date. Put your separation date in and the list below re-anchors to it. The items marked as deadlines are statutory or program clocks, not suggestions; those are the ones that cost money when they slip.
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Start the clock
- Pull your leave balance and plan terminal leave
Terminal leave has to be approved by your command, and the good dates go early.
- Request a copy of your medical record
You want everything documented BEFORE you separate. Undocumented conditions are far harder to claim later.
- Start the security clearance conversation
A current clearance is worth real money in cleared roles. Know its expiry and whether it transfers.
12 months out
- Attend TAP — then treat it as the floor, not the ceiling
TAP is mandatory and generic. It will not tell you what your MOS is worth in a specific metro.
- Translate your MOS into civilian language
Not a job title swap — the skills underneath it. Resume translator →
- Decide where you are going to live
State tax treatment of military retirement pay varies enormously, as does VA healthcare access. Compare metros →
- Apply for SkillBridge if you want it
Programs fill early and need command approval. Eligibility runs to the last 180 days of service. Find a program →
6 months out
- SkillBridge window opensdeadline
Eligibility begins within 180 days of separation, with command approval.
- File your VA disability claim under BDD if eligibledeadline
Benefits Delivery at Discharge lets you file before you separate so the claim is in process on day one. The filing window is limited — confirm current dates with the VA.
- Build the civilian resume properly
One page per decade of work, achievements not duties, and no acronyms a recruiter has to Google.
- Start networking before you need it
The job you want will come from a person, not a portal. Networking planner →
3 months out
- Confirm your terminal leave in writing
This is the step that quietly fails. Get the dates approved and documented. Run the leave math →
- Decide SGLI → VGLI
Your SGLI ends. Converting to VGLI has a hard clock on it once you separate — see below.
- Line up health coverage for the gapdeadline
Do not assume TRICARE continues. For most voluntary separations it does not.
- Scrub your LES and finance record
Fix pay errors now. Chasing DFAS after separation is materially harder.
1 month out
- Review your DD-214 draft before you sign
Errors here follow you for decades and are painful to correct. Decode your DD-214 →
- Get every document in your own hands
DD-214, medical records, training certificates, awards. Digital and paper copies both.
- Final medical and dental appointments
Use the coverage while you still have it.
- Register on eBenefits / VA.gov
Set up access before you lose your .mil address.
Separation date
- SGLI continues free for 120 daysdeadline
Free coverage runs 120 days from the date you leave. After that you are uninsured unless you have converted or bought private cover.
- TRICARE ends unless you qualify for TAMPdeadline
TAMP gives 180 days of coverage but is NOT automatic — it applies mainly to involuntary separations and specific categories. A routine voluntary ETS usually gets nothing.
Within 240 days after
- Apply for VGLI with no health questionsdeadline
Sign up within 240 days of leaving and you do not have to prove good health. Miss it and you must submit evidence you are insurable.
Within 1 year 120 days after
- Absolute VGLI deadlinedeadline
The last possible date to apply for VGLI at all. After this the option is gone permanently.
The three that catch people out
TRICARE probably does not continue. There's a widespread belief that everyone gets 180 days of TRICARE after separating. That's TAMP, and it is not automatic. It covers involuntary separations under honorable conditions, certain Guard and Reserve members coming off qualifying active-duty periods, stop-loss separations, and sole survivorship discharges. If you're separating voluntarily at the end of your contract, assume you have no coverage the day after — and plan for it.
SGLI runs out at 120 days. Free coverage continues for 120 days after you leave. VGLI is the conversion, and it has two clocks: apply within 240 days and no health questions are asked; after that you must prove you're insurable, and the option disappears entirely at 1 year and 120 days.
Undocumented conditions are hard to claim. If it isn't in your medical record before you separate, you carry the burden of connecting it to service afterward. Get it written down while you still have a military doctor.
Sources
- TAMP duration and the specific eligibility categories — TRICARE
- SGLI free coverage for 120 days after separation — VA
- VGLI 240-day no-health-questions window and the 1 year 120 day final deadline — VA
- SkillBridge eligibility within the final 180 days of service — DoD SkillBridge