Retirement Transition
Getting ready to retire? A little planning now sets you up for a smooth landing.
Review the 2027 Benefits eGuide for complete plan details.
At a Glance
Retirement affects your medical coverage, your 401(k), your life insurance, and more. Here's the order to think it through.
Your Last Day
Medical, Rx, Dental, and Vision coverage ends on the last day of the pay period in which your termination effective date occurs, with COBRA available.
EAP coverage ends on your last day unless you enroll in COBRA medical.
Life and AD&D Insurance end on your last day, too — you have 31 days to port or convert to an individual policy. Contact Voya to request a conversion/portability application packet.
Disability coverage also ends on your last day. If you are currently receiving disability benefits, you may be eligible to continue receiving them. Contact Voya to find out more.
Medicare & COBRA
Talk to SmartConnect. As you approach Medicare eligibility, SmartConnect's Medicare concierge offers one-on-one guidance to compare your options and enroll when you're ready.
If you’re already Medicare-eligible, COBRA can continue until your qualifying period ends, but it becomes secondary to Medicare — so you’ll need Medicare Part A and Part B in place to avoid any gaps in coverage.
COBRA lets you keep your health coverage for a limited time by paying the full cost yourself plus an administrative fee, bridging the gap while you transition.
Your 401(k)
You're always 100% vested in your contributions to the 401(k) Savings Plan. After 3 years of service, Office Depot's contributions are fully vested.
Decide what to do with your balance. You can leave your 401(k) invested with Fidelity, roll it into an IRA, or begin taking distributions, depending on your age and plan rules.
If you have an outstanding 401(k) loan, pay it off in full or continue payments through ACH — otherwise, the balance may be treated as a taxable distribution.
Your HSA & HCFSA
Your Health Savings Account (HSA) funds are yours to keep, even in retirement — they roll over year to year and stay usable tax-free for eligible expenses, including future medical needs in retirement.
Once you’re enrolled in Medicare, HSA contributions stop — but your existing balance remains yours to spend, tax-free, on qualified expenses.
Health Care Flexible Spending Account (HCFSA) expenses incurred before your separation date can still be reimbursed — submit your claims by March 31 of the following year.
Support Along the Way
Update your estate plan. LegalEASE can help you finalize a will or update your estate documents before you retire.
The EAP is available while you sort all of this out — free, confidential support 24/7, including legal and financial services for a confidential conversation about your finances, plus up to five free counseling sessions per issue per year for you and your household. (Remember: EAP coverage itself ends on your last day unless you elect COBRA medical.)
Keep this handy through every step
Confirm your separation date and what ends that day
Schedule a Medicare consultation with SmartConnect
If you're Medicare-eligible, get Part A and Part B in place before COBRA becomes secondary
Update your will or estate plan with LegalEASE
Use the EAP while you sort out the details — but remember its coverage ends on your separation date unless you elect COBRA medical
Contact Voya to request a conversion/portability application packet for your Life & AD&D Insurance if you would like to continue coverage
Pay off or continue making payments on any outstanding 401(k) loans
Submit outstanding HCFSA claims by March 31 of the following year
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