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Annual Enrollment 2025

Monday, April 28 - Friday, May 16, 2025.

The Annual Enrollment period is your once-a-year opportunity to enroll in, cancel, or change your health benefits without a qualifying life event. 

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Annual Enrollment is the only time you can make changes to your health coverage without a qualifying life event (such as marriage or birth). It’s important to review your current coverage, consider your family’s healthcare needs for the coming year, and take action if needed.
During Annual Enrollment, you can:
  • Enroll in new benefits you do not currently have
  • Modify existing coverage based on your evolving healthcare needs
  • Add or remove dependents in response to changes in your family situation
  • Cancel any unnecessary coverage (must show proof of alternate coverage)
  • Make no changes to your coverage—you don’t need to do anything, and your current coverage will carry over.

Your Benefit Options

Contact: Human Resources

CURRENT EMPLOYEES and NON-MEDICARE RETIREES:

The City of Boston offers three non-Medicare health insurance plans for benefits-eligible employees and retirees who are not eligible for Medicare.

  1. Compare plan offerings and rates effective July 1, 2025:
  2. See detailed information about what's covered under each plan:
  3. Before you enroll or make changes, be sure to check if your doctors and hospitals are in-network using the health plan’s provider lookup tools:
Need Help Choosing a Plan?

Attend one of our upcoming benefits fairs for in-person support, or contact us with questions.

MEdicare Retirees:

We offer five Medicare health insurance plans for retirees who are eligible for Medicare. All plans are designed to supplement Medicare Parts A & B, but they differ in how they deliver coverage.

  1. Compare plan offerings and rates effective July 1, 2025:
  2. See detailed information about what's covered under each plan:
  3. Review what's covered under our Metlife Dental insurance plan for retirees:
Need help understanding Medicare enrollment rules and timelines?

Read the 2025 Medicare and Your City of Boston Health Insurance Guide for detailed information, including when and how to apply for Medicare Parts A and B, what to do if you’re covering non-Medicare-eligible family members, a what happens if you delay Medicare enrollment. 

Take Action

Take Action
  1. Complete the combined Health and Life Insurance Application. Basic Life Insurance is required for all new health plan enrollees. Both enrollment forms are included in this file.
  2. Attach the required verification documents for any eligible dependents to be covered under your plan: 
    • To enroll a spouse: Submit a copy of your marriage certificate.
    • To enroll a former spouse:  Submit a copy of the divorce decree specifying that you must continue to provide coverage.
    • To enroll a child: Submit a copy of the child’s birth certificate (for adopted children, you’ll need to also include the adoption certificate). 
    • To enroll an adult disabled dependent: Contact the health plan directly and follow their procedures.
  3. Submit all required documents together by May 16, 2025 at 5:00 p.m.. Incomplete submissions will be voided.
    • Return by email: HBI@boston.gov
    • Drop off in-person: Health Benefits & Insurance Office, Room 807, Boston City Hall
RETIREE DENTAL PLAN ENROLLMENT:
  1. Use this form to enroll in dental coverage as a City of Boston retiree:
  1. Complete the Health Insurance Enrollment Form. No supporting documentation is needed, unless you are also adding or removing dependents.
  2. Submit your form by May 16, 2025 at 5:00 p.m.. 
    • Return by email: HBI@boston.gov
    • Drop off in-person: Health Benefits & Insurance Office, Room 807, Boston City Hall
  1. Complete the Health Insurance Enrollment Form. 
  2. Attach the required verification documents for any eligible dependents to be covered under your plan: 
    • To enroll a spouse: Submit a copy of your marriage certificate.
    • To enroll a former spouse:  Submit a copy of the divorce decree specifying that you must continue to provide coverage.
    • To enroll a child: Submit a copy of the child’s birth certificate (for adopted children, you’ll need to also include the adoption certificate). 
    • To enroll an adult disabled dependent: Contact the health plan directly and follow their procedures.
  3. Submit all required documents together by May 16, 2025 at 5:00 p.m.. Incomplete submissions will be voided.
    • Return by email: HBI@boston.gov
    • Drop off in-person: Health Benefits and Insurance Office, Room 807, Boston City Hall
  1. Use the standard Health Insurance Enrollment Form — this is the correct form for canceling coverage.
  2. On the form, check the box to cancel coverage and list any family members whose coverage you want to cancel.
  3. Submit the completed form by May 16, 2025 at 5:00 p.m. — incomplete submissions will be voided.
    •  Return by email: HBI@boston.gov
    • Drop off in-person: Health Benefits and Insurance Office, Room 807, Boston City Hall

If you do not wish to make changes to your current health insurance enrollment, you do not need to take any action. Your current selections will roll over.

Contact Us

Have questions or need help with your benefits? Explore the resources below, attend an in-person Benefits Fair, or contact the Health Benefits and Insurance team directly — we’re here to support you during Annual Enrollment and beyond.

Health Benefits Office

1 City Hall Square, Room 807

Boston, MA 02201

Benefits Fairs

Benefits Fairs
Annual Enrollment Benefits Fair
On May 1

May 1
Annual Enrollment Benefits Fair
On May 7

May 7
Annual Enrollment Benefits Fair
On May 13

May 13

Additional Resources

Glossary of Health Insurance Terms

Health insurance is full of terms you may not know. To help you better understand your coverage options, see this list

Medicare and your City of Boston Health Insurance

Need help understanding Medicare enrollment rules and timelines? Read this guide for detailed information.
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