Getting Your Money Right When Leaving the Military

October 1, 2026 - 00:07

Leaving the service comes with a paperwork window that does not stay open long. Miss it and the gap can be permanent.

The process starts before the final day. Service members can attend the Transition Assistance Program, which covers budgeting, resume writing and benefit basics. This is also the time to request a copy of the DD-214 worksheet and confirm the date of separation, because most deadlines count from that day.

Health coverage is the first hard deadline. TRICARE stays active for a set period after separation, usually 90 days for those retiring and 180 days for some others. After that, a new plan must be in place or coverage lapses. Veterans who served in combat zones may qualify for extended free care, but they still have to enroll.

Life insurance is next. Servicemembers' Group Life Insurance can be converted to Veterans' Group Life Insurance within one year and 120 days of leaving. Let that window close and a new policy may cost far more, or be denied for existing conditions.

Disability claims can be filed at any time, but filing within one year of separation often speeds up processing and can backdate payments to the separation date. Education benefits under the GI Bill require an application and a certificate of eligibility, and the clock on those benefits starts ticking once service ends.

The final step is a budget review. Pay, housing allowance and commissary access stop or change. Building a spending plan around the new income, before the first civilian paycheck arrives, prevents a shortfall in the months when bills still come due.