Retirement Planning Checklist

Last Updated March 7, 2024

Use this checklist in the years and months leading up to your retirement to make sure you are prepared.

Retiree Medical (COBRA/Medicare) Coverage Checklist

Six months before you turn 65:

If you are making HSA contributions through payroll, contact the RRD Benefits Center to stop your contributions.

Two to three months before your retirement date if you are turning age 65 or you are over age 65:

Learn about the benefits provided through Medicare (Parts A, B, C and D) and how they coordinate with any coverage you may choose to purchase through another medical program (e.g., AARP, supplement program).

Contact Allsup Benefits Coordination (free to you and your spouse currently enrolled in an RRD medical option) for help finding the best, most cost-effective medical plan.

Learn about how any remaining balance in your health savings account (HSA) may coordinate with any coverage you elect.

Consult with your financial planner to make sure you are planning for potential health care costs during your retirement.

Two to three months before your retirement date if you are less than age 64½:

Learn about your options through COBRA, the pricing, months of eligibility, and eligibility for your dependents. See your Medical and Prescription Drug Programs SPD.

Explore the coverage available through the individual market or the public health insurance exchange (healthcare.gov).

Learn about how any remaining balance in your health savings account (HSA) may coordinate with any coverage you elect.

Consult with your financial planner to make sure you are planning for potential health care costs during your retirement.

401(k) Checklist

When you reach age 50:

Consider making catch-up contributions to your 401(k) Savings Plan account. For up-to-date IRS contributions limits, visit irs.gov.

Within five or even 10 years of your expected retirement date:

Consider reviewing your contribution and investment strategy with a financial planner. If you decide to change your contributions or investment allocation, contact Fidelity.

Within 30 to 60 days after your retirement date:

If you are participating in the 401(k) Savings Plan when you retire, you will receive a kit at your home address. The kit will include information about your distribution options and consent requirements, plus a notice of important tax withholding information.

Flexible Spending Account (FSA) Checklist

Two to three months before your retirement date

Use any funds left in your FSA (Health Care FSA and/or Dependent Care FSA) to pay for eligible expenses since you can’t keep your account after you retire. You may be eligible for COBRA continuation of your FSA.

Pension Plan Checklist

Within one, five or even 10 years of your expected retirement date:

    If you were eligible, for the Pension Plan, request an estimate of your pension benefit from the Pension Service Center. For faster service, have your user ID and password available.

    Within 45 to 90 days before you want to start receiving your pension benefit (if eligible):

    Contact the Pension Service Center to start the application process. You will need your user ID and password.

    When you initiate your retirement with the Pension Service Center, you will receive additional information, including a letter and all the necessary information and forms that need to be completed to apply for your pension benefit. As indicated on the forms, you will need to have certain signatures notarized and return required supporting documentation.

    If you terminate employment and do not contact the Pension Service Center, you will receive a letter within three months after your separation date. The letter will indicate the amount of your pension benefit and when you can start to receive it.

    You can also find more information in your Summary Plan Description.

    Retirement Planning Resources

      Here are some additional resources and steps to consider.

      Leverage SupportLinc, RRD’s Employee Assistance Program (EAP), as you prepare for retirement. SupportLinc provides financial planning and counseling services that can help you think about and plan for the financial aspects of retirement, as well as the other things in your life that will change.

      Use MetLife Legal Plans for help to make an estate plan and create a will to ensure your assets go to the people you choose, and to help minimize income, gift and estate taxes. You can enroll in MetLife Legal Plans during Annual Enrollment in the fall.

      Review Welcome to 65: What You Need to Know about Your Benefits, which provides an overview of what happens to your RRD benefits when you retire (and some things you should know if you’re thinking about working for RRD after you are Medicare-eligible).

      Visit the Fidelity website for tools and resources to help you get and stay on track to your retirement savings goals.

      Contact Information


      RRD Benefits Center 
      1-877-RRD-4BEN
      (1-877-773-4236)

      Medicare
      1-800-633-4227
      TTY: 1-877-486-2048

      Healthcare.gov
      1-800-318-2596

      IRS
      1-800-829-1040

      HealthEquity
      1-866-346-5800

      Allsup 
      1-888-271-1173

      SupportLinc
      1-888-881-LINC
      (1-888-881-5462)

      MetLife Legal Plans
      1-800-821-6400

      Fidelity
      1-800-835-5095

      Pension Service Center
      1-866-767-1212