What it covers

• Your VA disability claim: the early window before you leave, and the 1-year deadline to get paid back to the day after you left

• When free SGLI ends, and your two VGLI deadlines

• Health care after you leave: TAMP, the CHCBP bridge plan, or TRICARE retiree enrollment

• Retiree dental and vision (FEDVIP) and your Survivor Benefit Plan choice

• One-time VA dental care (apply within 180 days)

• Your final move under the Joint Travel Regulations, based on your status: usually 180 days if you separate, 3 years if you retire from active duty, and when free storage ends

• Traditional Guard and Reserve retirement: TRICARE Reserve Select ending, TRICARE Retired Reserve, and your retired pay and TRICARE at age 60

• Guard and Reserve: the deadline to ask for your civilian job back (USERRA)

• Things with no deadline that are easy to forget: VA health care, records, your DD-214, unemployment, your TSP, and the GI Bill

Pick the status that fits you

• Separating from active duty: leaving for good, not retiring

• Retiring from active duty: retired pay starts right away. Includes Title 10 and Title 32 AGR and medical retirement.

• Retiring from the Guard or Reserve (traditional): moving to the Retired Reserve, with retired pay usually at 60

• Guard or Reserve coming off 31 or more days of orders and staying in your unit

Your status changes the rules. A traditional Guard or Reserve retirement, for example, has no government move, and its health care dates work differently. Spouses can use the tool too.

A planning tool, not the final word

Every date shows the office to confirm it with: your transportation office, retirement services, TRICARE, BENEFEDS, VA, or OSGLI. Your orders, component, and situation decide what applies. Check with them before you act.

Common questions

How long does SGLI last after I get out?

Your SGLI coverage continues for free for 120 days after you leave the military.

What is the VGLI deadline?

You can get VGLI with no health questions if you apply within 240 days after you leave. After that, you can still apply up to 1 year and 120 days after you leave, but you must show you are in good health.

When should I file my VA disability claim?

Best: 180 to 90 days before your last day, through Benefits Delivery at Discharge. You must be available for VA exams for 45 days after you file. Already out? File within 1 year after you leave and your benefits can start the day after your last day. Not ready? An intent to file holds your date for up to a year.

I am retiring from active duty. When do I have to enroll in TRICARE?

Within 90 days after your retirement date to keep coverage with no break. You can ask for retroactive enrollment up to 12 months after.

I am retiring from active duty. How long do I have for my final move?

Under the Joint Travel Regulations, a retiree with pay after 8 or more years of continuous active duty, or a disability retirement, has 3 years after leaving active duty to move to a home they choose. Free storage generally ends after 1 year. Confirm with your transportation office.

I am retiring from the Guard or Reserve. What dates matter?

Your TRICARE Reserve Select ends when you transfer to the Retired Reserve. Request TRICARE Retired Reserve within 90 days to avoid a gap. Free SGLI ends 120 days later, and your VGLI deadlines follow. At 60, your retired pay and TRICARE do not start on their own, so apply early. Confirm with your retirement office and TRICARE.

What happens to my health care if I separate?

Your active duty TRICARE ends when you leave unless you qualify for TAMP, which gives 180 more days to some people, such as those separated involuntarily or Guard and Reserve finishing more than 30 days in a row of contingency orders. Either way, you can buy up to 18 months of bridge coverage, with monthly premiums, through CHCBP if you enroll within 60 days after your TRICARE or TAMP ends.

Does this save my information?

No. Nothing you type is saved or sent. The calendar file is made on your own device.

Why I built this

The deadlines that come after you leave, the ones that cost real money, are spread across five agencies. This puts them in one place, with dates.

Brian Mongold, Chief Master Sergeant (retired)

Help keep this accurate

VA, TRICARE, BENEFEDS, and your personnel office are the official sources. Something wrong? Send me a note and I will fix it.

Version 2.0. Checked October 2026 against VA, TRICARE, BENEFEDS, OPM, Department of Labor pages, and the Joint Travel Regulations.

The fine print

Planning tool only. Always confirm with your servicing office. Unofficial. Not affiliated with VA or DoD. Not legal or financial advice.

More free tools

VA Claim Organizer, How to Read Your Military LES, Job Search Tracker, and GI Bill Tracker. See more Veterans tools or all free tools.