Transition Timeline: Money Moves in the 12 Months Around Separation

The dates below are anchored to your separation date, T-0. T-12 means twelve months before; T+6 means six months after. Your exact windows will vary with your situation, especially if you are retiring rather than separating, so treat this as the sequence and confirm the specifics for your case. For the hard-deadline items, the separation checklist covers each one in more detail.

• T-12 · Twelve months out

  Make it a decision, then start the reserve

  The first move is not financial. It is deciding, deliberately, that you are leaving and roughly when. Everything downstream sequences off that date.

  • Schedule the Transition Assistance Program early rather than at the last minute; the financial planning it forces is more useful with a year of runway than with a month.
  • Start building an income-gap reserve. Even smooth transitions often include a stretch between final military pay and stable civilian income, and VA claims and new-job start dates rarely cooperate with each other. Cash you set aside now is optionality later.
  • Pull your credit reports and clean up anything that would complicate renting, buying, or a security clearance conversation at your next employer.
• T-9 · Nine months out

  Records and claim prep

  Your medical record is the evidence base for your VA claim, and it is far easier to complete while you are still in the system that generated it.

  • Get a complete copy of your medical and dental records, and read them. Document conditions that were never formally recorded; get them into the record now, while you still can.
  • Start a personal file of everything transition will ask for: evaluations, awards, orders, training certificates. Future-you, applying for jobs and filing claims, will thank present-you.
  • If your household runs on two incomes or a working spouse's benefits, start mapping how coverage and cash flow change on the other side.
• T-6 · Six months out

  The BDD window opens

  The Benefits Delivery at Discharge program lets you file your VA disability claim before you separate, which is the single biggest thing you can do to shorten the gap between your last paycheck and your first benefit payment.

  • File your BDD claim. The window generally runs from 180 down to 90 days before separation; inside 90 days you can still file, but the expedited track closes. Confirm current rules with the VA.
  • Run the terminal leave math: take terminal leave and stay on pay and benefits longer, or sell leave back for a lump sum. The right answer depends on your job start date, your coverage needs, and taxes.
  • Review your insurance picture as a whole: what SGLI covers now, what your family actually needs after, and how you will replace it. Deciding this before separation means you are comparing options, not reacting to a deadline.
• T-3 · Three months out

  Coverage decisions and the final admin push

  The last quarter is administrative, and administration is where transitions quietly go wrong.

  • If you have not filed a VA claim yet, file now; the 90-day mark closes the BDD track but not the claim itself.
  • Map your health coverage bridge: TAMP eligibility if it applies to you, a new employer's plan and its start date, or purchased coverage. Know which one catches you on day one, not day thirty.
  • Attend your final out-processing briefings with a list of questions, not a signature pen. SBP elections for retirees happen here and are largely irreversible; do not make that call in the hallway.
• T-0 · Separation day

  Guard the paperwork

  One document rules the next decade of benefits: your DD-214.

  • Review your DD-214 before you sign it. Errors in dates, characterization, or awards are far easier to fix now than through corrections boards later.
  • Store multiple copies in multiple places, physical and digital.
  • Confirm your final pay computation, unused leave payout, and any outstanding travel claims. Update DEERS with your new status and contact information.
• T+1 to T+4 · The first months out

  The clocks that started at midnight

  Several windows opened the day you separated, and the most important one is easy to miss because nobody is around to remind you.

  • The SGLI to VGLI conversion window: you generally have about 240 days from separation to convert without answering health questions. If your health would make new coverage hard to get, this window may be the most valuable deadline of your entire transition. After it, conversion is still possible for a period but requires evidence of insurability. Confirm current windows with the VA.
  • If TAMP applies to you, know its end date; 180 days arrives faster than it sounds, and your next coverage should be arranged before it lapses, with CHCBP as the fallback bridge if you need one.
  • Enroll in VA healthcare if you are eligible. Enrollment is its own step, separate from your disability claim.
  • Notably absent from this list: your TSP. There is no deadline on that decision, which is exactly why it should be made deliberately, not in the chaos of month one. The TSP guide walks the options.
• T+6 to T+12 · The first year

  From transition to rhythm

  Somewhere in the back half of the first year, the goal shifts from managing a transition to running a household on its new normal.

  • Rebuild the plan on real numbers: actual civilian income, actual benefits as awarded, actual cost of living wherever you landed. The pre-separation plan was a forecast; this is the reconciliation.
  • Now make the TSP decision, with your full picture in view: new employer plan, tax situation, and what the rest of the plan needs the money to do.
  • Prepare for the transition-year tax return. A year that mixes military pay, possibly a leave payout, civilian income, a state move, and new tax-free VA income is more complicated than either the year before or the year after. It is the one return worth getting professional eyes on even if you never do so again.
  • Restate the goals. Separation was the mission for two years; something else is now. Write it down and point the plan at it.

Windows, program rules, and eligibility periods referenced here change over time and vary by situation, especially between separation and retirement. Confirm current specifics with your transition office, the VA, and the relevant agencies before acting on any deadline.