Every
deadline.
Every
entitlement.
One
countdown.
WheelsUp works backward from your separation or retirement date to map every milestone, leave window, and benefit — so nothing slips through the cracks. Not just a pay calculator: the whole flight plan.
Free tier · no spam — we'll only email you about WheelsUp
Separating is a deadline minefield
The rules live in dense, branch-specific regulations, and missing a window costs real money and real headaches. Most people track it in a spreadsheet and hope.
Windows that don't move
Terminal leave, SHPE/separation physical, TAPS, Skillbridge, VA BDD, SBP election — each has a hard deadline tied to your date.
Rules scattered across regs
AFI, Navy MILPERSMAN, Army AR, Marine MCO, Coast Guard — each branch has its own regs. Answers exist, but they're buried and hard to cross-check.
Mistakes cost money
Forfeited leave, a mistimed physical, a missed SBP or BDD window — small slips with four-figure consequences.
Your whole transition, mapped
Free tier covers the planning backbone. Pro unlocks the money math and hand-off tools.
Backward-planned timeline
A Gantt of every phase — PTDY, Skillbridge, terminal leave — auto-computed from your dates.
Milestone checklist
Every required action with its deadline and status — overdue items surfaced first.
Dashboard & countdowns
The dates that matter at a glance, with your next action front and center.
Retirement pay estimator
High-3, SBP, VA/CRDP, taxes — net pay with side-by-side scenarios.
Terminal leave vs. sell-back
See which nets more — allowances and tax handled — down to the dollar.
Printable brief, docs & contacts
A one-page hand-off for MPF/spouse, plus document and POC trackers. Multi-device sync + reminders.
Guard & Reserve calculators
Points-based retired pay, age-60 considerations, and CRDP modeling — specific to your component.
Divorce & retired pay
USFSPA pay-division estimate — disposable-pay math, the award formulas, the 50%/65% caps, and the 20/20/20 and 10/10 benefit flags.
VA disability & benefits explorer
What are you eligible for? Combined ratings, dependents, education benefits, home loans, state perks — all in one place.
Deadline reminders & sync
Email alerts for every milestone, cross-device sync, and a shareable one-page brief — so you and your family stay aligned.
Advanced financial tools Pro
Eight of these nine are in the app today; the expanded VA disability calculator is the one still rolling out. Go beyond the timeline — model the money decisions that shape your next 30 years.
How it works
Preflight, in three steps.
Set your dates
Branch, rank, base, and your separation or retirement date. Two minutes.
See your roadmap
Every deadline, leave window, and entitlement, computed and laid out for you.
Never miss a window
Check off milestones, run the numbers, and get reminders as dates approach.
Help shape WheelsUp
We're building this with separating and retiring service members — not for them. Which deadlines, entitlements, or calculators would make your transition easier? Tell us and we'll prioritize what gets built first.
Or just send us feedback — it comes straight to us, no email app needed.
Free to start — no card, and no account needed to look around.
Simple pricing
Start free. Unlock the advanced tools when you're ready — subscribe, or pay once and keep it for your whole transition.
Subscriptions renew automatically until cancelled; you can cancel yourself at any time from your account and keep access through the term you've paid for. Prices exclude any tax we're required to collect. Full terms: Payment, plans & refunds.
Free — no card needed
- Dashboard & countdowns
- Backward-planned timeline (Gantt)
- Milestone checklist
- Reference / FAQ
Pro unlocks
- Retirement pay estimator
- Terminal-leave vs. sell-back calculator
- Printable transition brief
- Documents & contacts trackers
- Multi-device sync + deadline reminders
Your data is private
Your plan is yours. We don't sell data, and you can export or delete it anytime. Privacy Policy · Consumer Health Data Policy
Estimate only
Calculations are planning estimates. Always verify with finance, MPF/MPS, MTF, and the VA before acting.
Built by a veteran, for veterans
Made by someone who went through the transition firsthand — every feature is something we actually needed.
FAQ
Which branches are supported?
All five: Air Force, Army, Navy, Marines, and Coast Guard. Each branch has its own rules, milestones, and calculators built in — set your branch when you start, and WheelsUp personalizes everything to your service.
Does this cover Guard and Reserve?
Yes. Guard/Reserve members get component-specific calculators: points-based retired pay (points ÷ 360), age-60 considerations, CRDP modeling, and Reserve-specific milestones like the Notice of Eligibility (NOE) and RCSBP. Active Duty, Guard, and Reserve all work in the same app.
What deadlines does it track?
Every milestone that matters: terminal leave, TAPS/transition class, Skillbridge application, VA BDD filing window, SBP election, separation pay eligibility, IDES/medical separation timelines, and more. Each has a hard deadline tied to your service end date.
Can I really see what I'll make in retirement?
Yes. The Pro retirement pay estimator models High-3, SBP, VA disability offset, CRDP (for some), plus taxes. You can run side-by-side scenarios (e.g., "SBP on vs. off" or "terminal leave vs. sell-back"). It's an estimate — always verify final numbers with finance.
Is my personal information safe?
Yes. Traffic is encrypted (HTTPS/TLS), data at rest is encrypted, and passwords are salted and hashed — we never see them. Your plan is isolated to your account, never sold or shared, and you can export or permanently delete it anytime. We also don't ask for SSN or other sensitive identifiers.
Can I sync across devices?
Yes. Pro members can access their plan on phone, tablet, and desktop, and get deadline reminders via email. Your data syncs instantly, and you can pause reminders or export a printable transition brief at any time.
Is this official military guidance?
No. WheelsUp is an independent planning tool built by someone who went through transition. Everything is an estimate — always verify dates and numbers with your finance office, MPF/MPS, MTF, or the VA before acting on them.
Subscription or one-time?
Both. Subscribe (quarterly or annual) for a low entry price, or pay once for lifetime access — choose what fits. Lifetime is a single charge that never renews.
What's included in Free vs. Pro?
Free: timeline, checklist, and countdowns. Pro: pay estimator, terminal leave calculator, Guard/Reserve calculators, printable brief, document trackers, multi-device sync, and deadline reminders.
Is WheelsUp available now?
Yes — WheelsUp is live. The free tier needs no card, and you can upgrade to Pro from inside your account at any time.