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 roadmap.
Free tier at launch · no spam — we'll only email you about WheelsUp.
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.
Terminal leave, SHPE/separation physical, TAPS, Skillbridge, VA BDD, SBP election — each has a hard deadline tied to your date.
DAFI/AFI, JTR, DoDI — the answers exist, but they're buried and branch-specific. Easy to miss, hard to cross-check.
Forfeited leave, a mistimed physical, a missed SBP or BDD window — small slips with four-figure consequences.
Free tier covers the planning backbone. Pro unlocks the money math and hand-off tools.
Go beyond the timeline — model the money decisions that shape your next 30 years. Rolling out through launch.
Project your TSP balance to retirement and beyond from contributions and return assumptions.
Combined-rating math with dependents, plus "what-if" scenarios for future ratings.
Education (GI Bill), VR&E training, VA home loan and more — see what you qualify for.
Full cost-vs-benefit, break-even age, and SBP-vs-life-insurance comparison.
States with VA-rating-based perks (property-tax exemptions and more) to factor into where you settle.
Model annual pay-raise scenarios into your High-3 and resulting retired pay.
Run thousands of scenarios — different VA ratings, SBP on/off, market returns — to see the long-run lifetime-dollar impact of each decision, not just a single estimate.
Branch, rank, base, and your separation or retirement date. Two minutes.
Every deadline, leave window, and entitlement, computed and laid out for you.
Check off milestones, run the numbers, and get reminders as dates approach.
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.
Share a feature idea →Or email us directly: feedback@militarywheelsup.com
Or join the waitlist to follow along and get early access.
Start free. Unlock the advanced tools when you're ready — subscribe, or pay once and keep it for your whole transition.
Limited to the first 100 members. Reserve now and lock lifetime access at the founding price. Help shape v1 and get every future update.
Your plan is yours. We don't sell data, and you can export or delete it anytime.
Calculations are planning estimates. Always verify with finance, MPF/MPS, MTF, and the VA before acting.
Made by someone who went through the transition firsthand — every feature is something we actually needed.
Air Force first (deep, cited content). Army, Navy, Marines, Space Force, and Coast Guard are on the roadmap — join the waitlist and tell us your branch so we can prioritize.
Yes. Traffic is encrypted in transit (HTTPS/TLS) and your data is encrypted at rest. Passwords are salted and hashed — never stored in plain text, and we can never see them. Your plan is isolated to your account, never sold or shared with third parties, and you can export or permanently delete it at any time. We also don't ask for sensitive identifiers like your SSN.
No. WheelsUp is an independent planning tool. Everything is an estimate — verify with finance, MPF/MPS, MTF, and the VA.
Both. Subscribe (quarterly/6-month/annual) for a low entry price, or pay once for lifetime access — whatever fits how you want to pay.
We're validating demand now. Join the waitlist or reserve one of the 100 founding-member spots to get early access and lock the founding price.
Join the waitlist for early access and the founding-member price. We'll only email about WheelsUp.
Prefer to lock the founding price now? Reserve a founding spot →