By when
The one-way doors
Most of what goes expensively wrong in a military career is not a decision made badly. It is a window that opened and closed while somebody was busy — and for a dozen of them, no board, no appeal and no hardship reopens it.
Who this is built for
This is a beta. Every figure here is an illustration built from what you have entered, not a statement of what you are owed — only DFAS, the VA and your own finance office can tell you that.
- Partly — read this — Guard or Reserve
- The 20-year letter and RCSBP windows are modelled from the dates you give. Windows keyed to a regular retirement will not apply to you.
- Partly — read this — Medical or disability retirement (Chapter 61)
- The disability evaluation timeline itself is not modelled — only the windows that follow separation.
- Partly — read this — Already retired
- The post-separation windows apply. The pre-separation ones are shown as closed, which is correct but not useful.
- Partly — read this — Spouse, former spouse or survivor
- The deemed-election and DIC windows are here. A survivor's own claim timeline is not.
- Built for you — Active duty heading for a 20-year retirement
- Built for you — Active duty separating before 20 years
- Built for you — Already separated
Every calculator here carries this list. See all of them side by side.
Read these before you scroll. They cannot be undone, so they are stated here rather than made into something you have to work for:
- File a VA claim, or an Intent to File, within a year of separating
- Last possible date to apply for VGLI at all
- Transfer the GI Bill while you are still serving
Windows below are computed against 2026-09-05, the date this page was published. Your browser has not set the current date yet.
11 waiting on a date from you
These are not 'no deadline'. They are deadlines this page cannot place on a calendar until you give it the date each one runs from.
Needs a date from youNo way back
File a VA claim, or an Intent to File, within a year of separating
Enter your separation or retirement date above and this becomes a date.
Miss it and a later award generally cannot begin the day after separation under this one-year rule. You can still file, and other effective-date or review rules may apply, but delayed filing can permanently forfeit months of back pay.
Commonly got wrong: That missing the year means you lose the benefit entirely. You do not — you can still claim, and should. What you lose is the back pay to separation, which is often the largest single cheque of the process.
38 CFR 3.400(b)(2)(i); 38 USC 5110(b)(1). Arellano v. McDonough, 598 U.S. 1 (2023) rejected equitable tolling for this specific one-year post-discharge grace period; it did not erase continuous pursuit, new-service-record, CUE, or other statutory effective-date routes. · VA Form 21-0966 (Intent to File), then VA Form 21-526EZ
Needs a date from youNo way back
Last possible date to apply for VGLI at all
Enter your separation or retirement date above and this becomes a date.
One year and 120 days after separation the door shuts completely, health evidence or not. There is no application after this and no board that reopens it.
38 USC 1977(e) · SGLV 8714
Needs a date from youNo way back
Transfer the GI Bill while you are still serving
Enter your separation or retirement date above and this becomes a date.
Transfer must be requested AND approved while you are in uniform, and it carries a four-year additional service obligation on top of the six already served. After separation it cannot be done at all — worth $80,000 to $180,000 in tuition and housing allowance.
Commonly got wrong: That you can transfer to your children after you retire. You cannot. This is among the most common and most expensive misunderstandings there is.
38 USC 3319; DoDI 1341.13 · milConnect Transfer of Education Benefits, in service only
Needs a date from youStatutory deadline
Complete the claim your Intent to File is holding open
Enter the date you filed your Intent to File above and this becomes a date.
An Intent to File reserves your effective date for one year. Let it lapse without filing the actual claim and the reservation dies with it — the effective date reverts to whenever you do file.
Commonly got wrong: That an Intent to File which lists your conditions IS the claim. It is not. It is a placeholder, and it expires.
38 CFR 3.155(b) · VA Form 21-526EZ
Needs a date from youStatutory deadline
Add a dependent to your VA award within a year of the event
Enter the date of your marriage, or a birth or adoption above and this becomes a date.
Add them later and the increase runs from the date you filed, not the date you married or the child was born. Worth about $17,000 over twenty years at 30% with a spouse, and over $200,000 at 100% with a spouse and two children.
Commonly got wrong: That the VA learns about a marriage or birth from DEERS. It does not — the two systems do not share dependency data, and the enrolment that gets your family a healthcare card does nothing for your compensation rate.
38 CFR 3.401(b)(1)(i); 38 USC 5110(n) · VA Form 21-686c
Needs a date from youStatutory deadline
Convert SGLI to VGLI while the guaranteed issue lasts
Enter your separation or retirement date above and this becomes a date.
Inside 240 days you are accepted with no health questions at all. After that you have until one year and 120 days, but only with proof of good health — which is exactly the proof an uninsurable veteran cannot supply. For them the loss is total and permanent.
Commonly got wrong: That the window is 120 days. That is the SGLI free-extension period, not the VGLI guaranteed-issue window — conflating them costs people the good months.
38 USC 1977(e); 38 CFR 9.2(c) · SGLV 8714
Needs a date from youStatutory deadline
Enrol in a retiree TRICARE plan
Enter your separation or retirement date above and this becomes a date.
Cover does not carry over at retirement; it requires an affirmative enrolment. Miss the window and you are limited to space-available military care until an Open Season or a new qualifying event, paying full cost for anything else in between.
Commonly got wrong: That your existing plan continues into retirement. It stops, and the failure surfaces as a denied claim rather than a warning.
32 CFR 199.17(o); retroactive enrolment available up to 12 months · milConnect, or your regional contractor
Needs a date from youStatutory deadline
Return your RCSBP election after the 20-year letter
Enter the date of your 20-year letter (Notification of Eligibility) above and this becomes a date.
Silence does not decline. Failing to return the election auto-enrols you in Option C — the most expensive option — irrevocably, with premiums accruing and any unpaid balance later deducted from the annuity.
Commonly got wrong: That doing nothing keeps you out of it. Inaction produces the most expensive outcome available, which is the opposite of what almost everybody assumes.
10 USC 1448(a)(2)(B); irrevocable under 1448(a)(4)(B) · DD 2656-5
Needs a date from youStatutory deadline
Make your SBP election before retired pay starts
Enter the date your retired pay starts above and this becomes a date.
The election locks on the first day you are entitled to retired pay. Declining without your spouse's notarised concurrence does not decline it — it enrols you at FULL spouse coverage, at 6.5% of retired pay for up to 360 months.
Commonly got wrong: That not signing up means not being in it. The default runs the other way, and the concurrence requirement is what catches people.
10 USC 1448(a)(4)(A) · DD 2656; DD 2656-2 to withdraw later
Needs a date from youStatutory deadline
The third-year window to terminate SBP coverage
Enter the date your retired pay starts above and this becomes a date.
The ordinary termination window runs during months 25 through 36 of receiving retired pay. It opens on the second anniversary and ends immediately before the third anniversary. Termination is permanent, requires the covered spouse or other covered beneficiary to concur where applicable, and does not refund prior premiums.
Commonly got wrong: That the second anniversary is the deadline. It is the opening date. The calculator must show the full third-year window rather than call it closed as the window begins.
10 USC 1448a(a), (b), (g); DFAS, Changing or Stopping Your Coverage (third-year termination window) · DD 2656-2, with required beneficiary concurrence
Needs a date from youStatutory deadline
Request a waiver of a VA debt
Enter the date of your first VA debt notice above and this becomes a date.
Miss it and the full debt is collected by offset against your monthly compensation, whatever the hardship.
Commonly got wrong: That the window is 180 days. It was, until the end of 2024 — virtually all secondary guidance is still stale, and following it costs people nine months they actually have.
38 USC 5302(a)(1); 38 CFR 1.963(b). Extended from 180 days to one year by Pub. L. 117-328 §254(a), effective 29 December 2024. · VA Form 5655, with a personal statement
Why the list shows things it cannot date
A tool like this could show only the windows it has your dates for. It would look tidier and it would be dishonest — a short list reads as these are my deadlines, when it actually means these are the ones you gave it enough information to compute. The omission is invisible, and it is the half that costs money.
So every window that applies to you appears whether or not it can be placed on a calendar, and the ones that cannot say exactly which date they need. The same rule governs the questions about your situation: an unanswered one means unknown, and the deadline stays on the list rather than being dropped on a guess.
Three that are commonly believed backwards
- The VA debt waiver window is one year, not 180 days.It changed at the end of 2024, and most guidance still online is stale. Following it costs people nine months they actually have.
- VGLI guaranteed issue runs 240 days, not 120.The 120-day figure is the SGLI free extension — a different thing. Conflating them costs the months where no health questions are asked.
- Doing nothing about SBP does not decline it.Declining without a spouse's notarised concurrence enrols you at full coverage, and letting the reserve election lapse elects the most expensive option available. Inaction is the costly choice in both cases, which is the opposite of what almost everyone assumes.
Every window here carries its statute so you can check it rather than take this site's word for it. Estimates and explanation only — not legal, tax or VA advice. Your dates stay in your own browser.