Separating from the military sets off a series of financial deadlines that don’t run on the same schedule, and most of them aren’t automatic. Health coverage, life insurance, Department of Veterans Affairs disability filing and retirement account decisions all run on their own separate clocks, and missing any one of them can mean a gap in coverage or a benefit that closes for good. Here’s how the sequence goes, from before separation through the end of the first year.
Before Separation: 90 to 180 Days Out
The window to start planning opens well before your separation date. Veterans and service members can file a disability claim before leaving service through VA’s Benefits Delivery at Discharge program, which generally opens 90 to 180 days before separation. Filing during this window means a claim can be fully developed and, in many cases, decided closer to your exact separation date rather than months afterward.
This is also the window to request your Service Treatment Records while you still have CAC access to military medical systems. Getting a full service treatment record from the National Archives may take months, making it worthwhile to request before you lose easy digital access.
The Transition Assistance Program, a mandatory pre-separation program covering financial planning, employment assistance and benefits orientation, is required for most separating service members with more than 180 days of active service. This is also the time to review Thrift Savings Plan fund elections and rollover options, and to model how any Blended Retirement System matching contributions factor into retirement planning going forward.
Day of Separation
Basic Allowance for Housing and Basic Allowance for Subsistence both stop on your separation date, according to the Defense Finance and Accounting Service. There’s no grace period on either allowance, which makes budgeting for the immediate post-separation weeks, especially before a first civilian paycheck or VA payment arrives, one of the more commonly underestimated parts of the transition.
The First 120 Days: Free Life Insurance — but Only Temporarily
Servicemembers’ Group Life Insurance continues at no cost for 120 days after separation, according to Military.com’s own guide to converting SGLI coverage. After that point, SGLI coverage ends entirely unless you’ve converted it to Veterans’ Group Life Insurance, a separate policy administered by Prudential on the VA’s behalf.
Related: How Does SGLI Convert to VGLI After Separation, and What’s the 2026 Deadline?
Day 180: The TAMP Deadline, if It Applies to You
The Transitional Assistance Management Program provides 180 days of premium-free Tricare coverage after certain separations. The detail that catches people off guard is that TAMP is not automatic and does not apply to everyone. The program generally covers involuntary separations, early retirement programs and certain force-shaping events, not routine end-of-enlistment discharges. Veterans who assume they have a Tricare bridge and don’t actually qualify for TAMP can find themselves with no health coverage at all starting on Day 1 after separation.
Related: Transitional Assistance Management Program
Veterans transitioning into the National Guard or reserve have a separate option in Tricare Reserve Select, priced in 2026 at $57.88 a month for the member alone or $286.66 a month for family coverage.
Related: Tricare Reserve Select Overview
Day 240: The Life Insurance Deadline Worth Circling
The most consequential deadline in the entire transition timeline, for anyone with any health concerns at all, is the 240-day guaranteed-acceptance window to convert SGLI to VGLI. Applying within 240 days of separation means converting without answering health questions or undergoing a medical exam, regardless of current health status. After Day 240, conversion still remains possible, but only with evidence of insurability, meaning a veteran with a new or worsened health condition could be charged significantly more, or denied coverage entirely, for the same policy that would have been guaranteed just weeks earlier.
Family Servicemembers’ Group Life Insurance, which covers spouses and children while on active duty, cannot be converted to VGLI at all, according to a 2026 transition checklist published by First Command. Veterans need to separately arrange coverage for dependents through a new employer’s plan or a private policy before that coverage lapses.
Day 485: The Absolute Final Deadline
Even with the guaranteed-acceptance window closed, veterans still have until 485 days after separation — one year and 120 days — to convert SGLI to VGLI at all. After Day 485, the option to convert disappears, regardless of health status or willingness to pay a higher premium.
Throughout the Year: The Decisions With No Fixed Deadline
Not every financial decision in the first year runs on a countdown clock, but that doesn’t make them less important. Thrift Savings Plan funds can be left in place, rolled into a civilian 401(k), or moved into an IRA. Retirees with 20 or more years of service also need to finalize any Survivor Benefit Plan elections tied to their pension, a decision that becomes considerably harder to change after the fact, according to a transition financial checklist published by Navy Federal Credit Union.
Veterans should also compare any civilian job offer against total military compensation, not just base pay, factoring in the value of allowances and benefits that don’t have a direct civilian equivalent.
Related: What to Do With Your First Civilian Paycheck After Military Separation
The Bottom Line
Every deadline in this timeline exists independently of the others. Qualifying for TAMP doesn’t affect your SGLI conversion window. Filing a VA claim through the Benefits Delivery at Discharge program doesn’t change when BAH stops. The safest approach is to write down your exact separation date and calculate each deadline from it, rather than relying on memory or assuming one benefit’s timeline mirrors another’s. A financial adviser experienced with military benefits, or a transition counselor at an installation’s TAP office, can help build that calendar before separation happens.
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