Short answers to the questions that come up again and again. Each one is grounded in the regulation or statute that decides it, and each links to the guide that covers it in full. If an answer here disagrees with something you have been told, the citation is the thing to check.
When do I have to start TAP?
No later than 365 days before your separation or retirement date. That is the DoD-wide rule in DoDI 1332.35, and the services repeat it in their own instructions. It is a floor, not a target — starting at the 365-day mark leaves you doing TAP while you are also doing terminal leave planning, permissive TDY and a job search.
Involuntary separations and some short-notice cases have their own compressed timelines, so if your date moved, ask rather than assume.
Covered fully in The military retirement timeline.
How long do I have to enrol in TRICARE after I retire?
90 days after your retirement date. Retiring is a TRICARE Qualifying Life Event, and your active-duty coverage does not become retiree coverage on its own — you have to enrol. Re-enrol inside the 90 days and there is no break in coverage.
If you miss it, you may request a retroactive enrolment up to 12 months from your retirement date. It is a request, not an entitlement, and coverage has already broken by then.
Covered fully in TRICARE after you retire: Prime, Select and For Life compared.
Do I have to take Medicare Part B at 65 to keep TRICARE?
Yes. This is the most expensive misunderstanding in military retirement. 10 U.S.C. §1086(d) is written as a bar plus an exception: someone entitled to Medicare Part A is not eligible for TRICARE under that section unless they are enrolled in Part B.
So Part B is not an optional extra sitting on top of TRICARE. It is the thing that keeps TRICARE alive at 65. Decline it and you do not save a premium — you lose the coverage. The same applies overseas, where Part B is required to stay TRICARE-eligible even though Medicare does not cover you there.
Covered fully in TRICARE after you retire.
Do I lose TRICARE the day I separate?
Not if you separate in one of the categories covered by 10 U.S.C. §1145. Those members and their dependents get 180 days of transitional TRICARE at no premium, starting the day of separation, under the Transitional Assistance Management Program.
It is not universal — §1145(a)(2) lists the qualifying categories, and an ordinary end of a first enlistment is often not one of them. Retirees are a separate case entirely: they get retiree TRICARE, not TAMP.
Covered fully in TAMP: the 180 days most separators don't know they have.
Does VA disability reduce my retired pay?
By default yes — you waive a dollar of retired pay for each dollar of VA compensation. Concurrent Retirement and Disability Pay under 10 U.S.C. §1414 undoes that waiver for retirees who qualify, letting the two stack instead of offsetting.
The usual qualifying route is a 20-year retirement with a VA rating of 50% or more. Below that threshold the waiver still applies, which is why a rating increase from 40% to 50% can be worth far more than the rating change alone suggests.
Covered fully in CRDP: when retired pay and VA compensation stack.
Is VA disability compensation taxable?
No. 38 U.S.C. §5301(a)(1) exempts payments made under any law administered by the Secretary of Veterans Affairs — which covers VA disability compensation, and the GI Bill education stipend along with it.
The edge most people miss is what the exemption does not reach: property bought with those payments. Save your VA compensation and invest it, and the growth on it is ordinary taxable investment income. The payment is exempt; what you turn it into is not.
Covered fully in VA disability math: why 50 + 30 ≠ 80.
When can I file a BDD claim?
Between 180 and 90 days before separation. Benefits Delivery at Discharge is the VA's pre-discharge claim path, and the window is genuinely two-sided: file earlier than 180 days out and it is too early, file later than 90 days out and you have missed BDD.
The point of it is timing — a claim filed in that window can be decided at or near your separation date, rather than starting the clock the day you take off the uniform.
Covered fully in The VA BDD claim timeline.
How is Guard and Reserve retired pay worked out?
By points, divided by 360. Your creditable retirement points across a career are totalled under 10 U.S.C. §12733 and divided by 360 to give the equivalent years of service that drive the multiplier — so 5,400 points is 15 equivalent years, whatever the calendar says.
Two things follow that surprise people: pay normally starts at age 60, not at retirement, and there is a real cap on the number of inactive-duty points creditable per year, which has changed several times over the decades.
Covered fully in Guard and Reserve retirement: points ÷ 360.
What is the 10/10 rule in a military divorce?
It is a payment rule, not an entitlement rule, and that distinction is where most of the confusion lives. Under 10 U.S.C. §1408, DFAS will pay a former spouse's court-ordered share of retired pay directly only when the marriage overlapped at least 10 years of creditable service.
It does not decide whether a former spouse is awarded a share — that is the court's decision under state law. Fail the 10/10 overlap and the award can still stand; it just gets paid by the retiree rather than by DFAS.
Covered fully in Divorce and military retirement: USFSPA, 10/10, and the frozen benefit.
Can I use SkillBridge and terminal leave together?
Usually yes, but how much of each you get depends on your service, and the services do not limit the same thing. The Air Force, Space Force and Army cap the SkillBridge programme; the Navy and Marine Corps cap the whole absence — SkillBridge, terminal leave and permissive TDY together.
The practical consequence: one identical plan can clear one service's rules and breach another's. Terminal leave also comes last in the sequence in all five services. Build the plan against your own service's instruction, not a figure someone quoted from a different branch.
Covered fully in SkillBridge, the complete guide.
Every one of these is a date or a number in your own plan. WheelsUp back-plans them from your actual separation date and branch, with the citation attached to each card.
Sources
- DoDI 1332.35 (with the service supplements) — transition assistance must begin no later than 365 days before separation or retirement
- Defense Health Agency, Retiring — retirement as a Qualifying Life Event, the 90-day enrolment window, and the retroactive-enrolment request up to 12 months
- 10 U.S.C. §1086(d) — (d)(1) bars a person entitled to Medicare Part A from TRICARE under that section; (d)(2)(A) restores it for a person enrolled in Part B. Read together, Part B is what preserves TRICARE at 65
- 10 U.S.C. §1145 — (a)(1) transitional health care for the member and dependents; (a)(2) the qualifying categories; (a)(4) the 180-day period beginning on the date of separation
- 10 U.S.C. §1414 — Concurrent Retirement and Disability Pay: qualifying retirees receive both retired pay and VA compensation without the §5305 waiver
- 38 U.S.C. §5301(a)(1) — payments under any law administered by the Secretary are exempt from taxation, and the exemption does not extend to property purchased in part or wholly out of such payments
- 10 U.S.C. §§12731–12739 — non-regular retirement; §12733 the computation of creditable retirement points, divided by 360 for equivalent years of service
- 10 U.S.C. §1408 — the Uniformed Services Former Spouses' Protection Act: direct payment by the Secretary requires 10 years of marriage overlapping 10 years of creditable service
- DoDI 1322.29 and the five services' own SkillBridge instructions — the programme-versus-absence distinction in what each service caps
Spot an error? Tell us — citations are the product here.