The Financial Separation Checklist

Every item below has two things: what to do, and when the window closes. Windows marked in red are hard deadlines set by law or regulation. The others are strong recommendations where earlier is meaningfully better. Timelines are as of this writing and do change, so confirm current rules with the VA, DFAS, or your transition office before relying on a specific date.

Download the Checklist (PDF)
One page, printable, no email required.

The sequence

Phase one · As soon as your separation date is set

• Cash reserve · start now, it takes months

  Build the income-gap reserve

  There is often a gap between your final military paycheck and your first full civilian one, and it can run weeks to months once you account for job-start timing, payroll cycles, and any VA compensation processing time. Generic emergency-fund guidance does not model this gap. Build a cash reserve specifically sized to your realistic gap before your separation date. This is first on the list because it takes the longest, and because this single move removes the pressure that causes rushed decisions on everything else on this page.

• VA disability · window: 180 to 90 days before separation

  File your VA disability claim early

  The Benefits Delivery at Discharge (BDD) program lets you file your claim between 180 and 90 days before separation, so the VA can work it while you are still on active duty and, ideally, have a decision shortly after your date. Filing early means your medical records are fresh, your providers are reachable, and compensation can start close to separation rather than months later.

  Document everything now. Every clinic visit, every injury, every condition, however minor it seems at 30. Claims are built on service treatment records, and the strongest record is the one written down at the time. If your window has already passed, file anyway; you simply file through the standard process after separation.

• Final pay · decide before out-processing

  Run terminal leave versus selling leave, both ways

  Taking terminal leave keeps you on active-duty pay and benefits, including allowances, while you start the next chapter. Selling leave back converts it to a lump sum, but the payout is based on base pay only and is taxable. The right answer depends on your job timing, your healthcare bridge, and your cash needs. Run the numbers both ways rather than defaulting to whichever your unit does out of habit.

Phase two · The final weeks and out-processing

• Healthcare · confirm before your separation date

  Line up TRICARE transition coverage

  Retirees keep TRICARE. Separating members do not, and the gap between military healthcare and an employer plan is where families get exposed. Two programs bridge it. The Transitional Assistance Management Program (TAMP) provides about 180 days of premium-free coverage for members who qualify, typically through involuntary separation and certain other categories. The Continued Health Care Benefit Program (CHCBP) is a premium-based option that can extend coverage up to 18 months beyond that.

  Confirm your TAMP eligibility before your separation date, not after. If you do not qualify, price CHCBP against a marketplace or employer plan so the decision is deliberate rather than a scramble.

• Family records · while the personnel office is easy to reach

  Update DEERS

  The Defense Enrollment Eligibility Reporting System drives your family's benefit eligibility, including transitional TRICARE coverage. Make sure every family member's information, and your own contact information, is current before you lose easy access to a personnel office. An out-of-date DEERS record is a common and entirely avoidable reason benefits get interrupted.

• Survivor benefits · retirees: decision at retirement

  Make the SBP election deliberately

  For those retiring rather than separating, the Survivor Benefit Plan election is made at retirement and is one of the least reversible decisions in the entire transition. It determines whether a portion of your retired pay continues to your survivors. The decision deserves careful analysis: the cost of coverage, your family's needs, your health and insurability, and what other survivor resources exist. Declining SBP generally requires your spouse's notarized concurrence, which is a signal of how consequential the government considers it. Decide with the math in front of you, not under out-processing time pressure.

• Records · at the out-processing table

  Secure your DD-214

  The DD-214 is the key that unlocks nearly everything else: VA benefits, the GI Bill, VA home loans, veterans' preference in hiring, even some state property-tax exemptions. Get certified copies, store one digitally and one physically, and consider recording a copy with your county recorder where that service is offered. Verify every field before you sign it on your way out. Correcting an error later is a slow process; catching it at the table takes minutes.

• Taxes · effective day one as a civilian

  Plan your state taxes and residency

  Active-duty members enjoy residency protections that end with your service. Where you live on day one as a civilian, and where your income is earned, changes your state tax picture immediately. If your transition includes a move, the sequencing of the move against your separation and start dates can matter. Confirm the specifics with a tax professional for your states before the date, so the answer is set when the protections lapse.

Phase three · After separation, the clocks are running

• Healthcare · enroll early

  Enroll in VA healthcare

  VA healthcare enrollment is separate from your disability claim, and many veterans qualify regardless of whether they have a rating. Recent combat veterans generally have an enhanced enrollment period after discharge. Enrolling early does two things: it establishes you in the system before you need it, and it creates a continuous medical record on the civilian side, which supports everything from routine care to future claims.

• Life insurance · free coverage ends around day 120; the no-health-review window around day 240

  Convert SGLI before the clock runs out

  Your Servicemembers' Group Life Insurance does not stop the day you separate. Coverage generally continues for 120 days at no cost. After that, you have choices: convert to Veterans' Group Life Insurance (VGLI), convert to a commercial policy, or replace the coverage privately.

  The detail that matters most: if you apply for VGLI within roughly 240 days of separation, you generally cannot be turned down for health reasons. Apply after that inside the full application window and you may need to prove good health. If you developed any medical condition during service, that no-health-review window can be the difference between having life insurance and not. If your family depends on your income, do not let this one drift past the four-month mark.

• Retirement savings · beneficiaries now, structure decision on purpose

  Make the TSP decision on purpose

  Your Thrift Savings Plan does not expire and there is no forced deadline, which is exactly why it drifts. You generally can no longer contribute after separation, but the account stays invested, and the question of which of the four options fits depends on your situation. The default many separating members land in, by inaction, is decades of savings sitting in an allocation nobody chose for their new situation. We cover the full decision in What to Do With Your TSP After You Separate.

  One immediate action regardless: update your contact information and beneficiaries with the TSP directly, since changes no longer flow through your service records.

Download the Checklist (PDF)
One page, printable, no email required.