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Benefits Available to City Retirees

You can find out what benefits you have as a City of Boston retiree on this website.

For health insurance questions, contact:

Health Benefits Office

1 City Hall Square, Room 807

Boston, MA 02201

Email: | Phone: 617-635-4570

Fax: 617-635-3932

Office hours: Monday through Friday, 9 a.m. - 5 p.m.

Insurance eligibility


If you receive a retirement or pension allowance from the Boston Retirement Board, you are eligible to take part in the City of Boston health and life insurance.

Family members:

If you are eligible for health insurance, you may also cover your family members. Eligible family members include:

  • children, until they reach age 26
  • your spouse (as defined by Massachusetts state law), and
  • any disabled children you have over the age of 26. They need to depend on you for principal support and be unable to earn a living due to their mental or physical condition. The disability needs to have started before age 19 (or before age 26 if they still depended on you for principal support), and your child must continue to meet the plan’s definition of "disabled." Contact your health plan directly to confirm disability status.
Enrolling family members

If you wish to enroll family members, you must provide documents that verify their eligibility:

  • For your spouse, you need to provide a certified copy of your marriage certificate from the town or city where you were married.
  • For your children, you must provide a certified copy of their birth or adoption certificates, or legal guardian paperwork. We will accept a birth or hospital announcement if a child was born within the last 30 days.
  • We also need Social Security Numbers for your spouse and dependents. 

Mandatory Medicare


Effective July 1, 2011, Massachusetts law mandated that all cities and towns require retirees age 65 and older to apply for Medicare Parts A and B. If eligible, these retirees must also transfer to a Medicare plan to continue their health insurance coverage.

This includes:
  • retirees
  • the spouses of retirees
  • Medicare-eligible dependent children (if they are disabled), and
  • surviving spouses.

If you are eligible to receive Medicate Part A for free, you must enroll in both Medicare Parts A and B. To learn more, review the Medicare and your City of Boston health insurance fact sheet.

Non-Medicare Health Plans

If you are retired but are not eligible for Medicare, you may remain enrolled in one of the City's non-Medicare health plans. The health plan options and retiree contributions are the same as that of active employees.

The City offers three non-Medicare plans. If you are living outside of Massachusetts for more than 90 days each year, you must enroll in the PPO plan. View the non-Medicare plan comparison chart (effective July 1, 2024 through June 30, 2025).

Download Non-Medicare Application

Medicare plans

By law, all retirees, spouses, and dependents of retirees who are eligible for Medicare must:

  • apply for Medicare Parts A and B, and
  • transfer to a Medicare plan to continue health insurance coverage.

We offer six Medicare plans to supplement Medicare Parts A and B for our retirees. 

Please submit completed applications and supporting documents (such as marriage certificate or birth certificate) to the Health Benefits and Insurance Office. Forms can be faxed, emailed, or mailed:

Health Benefits and Insurance 

Boston City Hall, Room 807 

Boston, MA 02201

Fax: 617-635-3932 


Medicare Plans contact info and forms

Life Insurance

Basic Term Coverage:

The City offers a group term life insurance to employees and retirees in the amount of $5,000. The City and the employee or retiree each pay for half of the cost for the benefit.

Optional Life insurance:

Employees can also take part in additional term life insurance coverage based on their salary. The maximum insurance amount is $74,000. We base the cost on an employee’s age, and the employee pays the full amount.

After you retire, the cost increases to $3.95 for every $1,000 worth of coverage. Coverage ends at age 75, at which time all benefits end with the City of Boston. You are then able to convert your coverage into a Boston Mutual plan.

Dental and vision

The City offers 100% retiree-paid dental coverage for retirees. You may be eligible to continue your dental benefits for up to 36 months with COBRA through the Massachusetts Public Employees Fund or BCBS for Boston Public Schools managerial employees.

Retiree Dental:

Download MetLife Retiree Dental Enrollment Form

Some retirees may opt to continue their dental and vision plans through their former union. These unions include:

  • the Boston Teachers Union
  • the Boston Police Patrolmen’s Association
  • the Boston Police Superior Officers Association
  • the Boston Police Detectives Benevolent Society, and
  • the Boston Firefighters L718.

Employees in these unions should contact their union representative for more information about eligibility as a retiree.

Savings and Investment Benefits

Flexible Spending Accounts

These programs allow employees to set aside a portion of their paycheck tax-free to pay for expenses, including:

  • dependent care
  • medical and dental care, and
  • work-related parking fees and mass transit.

The result is a reduction in your taxable income, which will give you an increase in your take-home pay.

Please keep in mind:
  • Annual Enrollment for Flexible Spending is every fall, with coverage effective on January 1.
  • Enrollees retiring before the end of the plan year on December 31 may use their debit card up to their retirement date.
  • After retirement, retirees have until the end of the plan year to submit paper claims for services they used before their retirement date.
  • Please plan ahead when you enroll in Flexible Spending in the year that you retire to ensure you do not lose money.

We offer three types of retirement planning programs:


City workers are welcome to join the City of Boston Credit Union. The credit union offers competitive interest rates, club discounts, and other benefits.

Benefits Billing

If you receive a benefits billing statement related to your City of Boston health or life insurance, you have two options to pay for the coverage: 

Make a check out to 'City of Boston':


Attn: Health Benefits and Insurance

Room 807

Boston, MA 02201

Pay online
  • Visit our payment website. Please refer to your Benefits Billing Statement. Complete the requested information to submit your payment online.
  • Payments made by electronic check / ACH are not subject to a service charge. The online credit card service charge is 2.75 percent of the total payment ($1 minimum). 
  • Upon receipt of your payment, it will be processed and posted to your account within two to four business days.

NOTE: If you are receiving an active paycheck or pension, your deductions will not be affected.

Common questions


Retirees pay the same percentage of health and life insurance premiums as active employees. Premiums are withheld from your monthly retirement or pension check, and we collect them one month in advance. For example, June deductions pay for coverage in July.

Retiree health insurance coverage follows the same rules as coverage for active employees. Retirees can newly enroll in or change plans during the annual enrollment period each spring for coverage that begins on July 1. Retirees can also enroll any time during the year year due to a loss of coverage.

Retirees can add or remove dependents due to a qualifying life event, including a:

  • a marriage or birth
  • a spouse or dependent losing their coverage, or
  • a spouse or dependent gaining coverage elsewhere. You need to drop them from your plan within 30 days of them getting new coverage.

You can update your address by completing the Change of Address form and submitting it to the health benefits office within 30 days of your move.

If you move out of your plan service area, this is considered a qualifying event, and you can enroll in a different plan within 30 days. For questions about the plan service areas, please call Health Benefits at 617-635-4570.

Upon a retiree's death, their surviving spouse may continue coverage at the same cost as when the retiree was alive. Please also keep in mind:

  • Choosing Option A, B, or C for your pension allowance does not affect your surviving spouse’s eligibility for continued health insurance. But, if you choose Option A or B, they your spouse must pay premiums to the City.
  • If you choose Option C for your pension allowance, we will take monthly deductions from your surviving spouse’s pension check.
  • Surviving spouses are no longer eligible for health insurance if they remarry.

Effective July 1, 2011, Massachusetts law mandated that all cities and towns require retirees age 65 and older to apply for Medicare Parts A and B. If eligible, these retirees must also transfer to a Medicare plan to continue their health insurance coverage.

This includes:

  • retirees
  • the spouses of retirees
  • Medicare eligible dependent children (if they are disabled), and
  • surviving spouses.

If you are eligible to receive Medicate Part A for free, you must enroll in both Medicare Parts A and B.

You could be eligible for Medicare Part A for free if:

  • you worked 40 credits into Social Security
  • you have a current spouse, former spouse, or a deceased spouse who worked 40 credits into Social Security
  • you paid the Medicare tax (employees hired after July 1, 1986 have paid the Medicare tax), or
  • you have Military service that counts toward eligibility.

This list is not comprehensive. Even if you think you are not eligible for Medicare, you must go through the process of applying through Social Security.

Medicare Part A - Hospital Inpatient Insurance

The insurance helps cover inpatient hospital care, skilled nursing facility care, nursing home care, hospice, and home health care. This is not for long-term care, and limits apply.

If you are eligible for Medicare, Part A is FREE.

Medicare Part B - Medical Out-Patient Insurance

This insurance helps cover doctors’ services, hospital outpatient care, and home health care. It also helps cover some preventive services. Please keep in mind:

  • Most people pay the standard monthly Medicare Part B premium ($121.80 in 2016). 
  • Higher Part B premiums (Income-related Monthly Adjustment Amounts) may apply to some retirees based on their income level. 
  • If you collect a Social Security check, your premium will be withheld from your check.
  • If you do not collect a Social Security check, you will be billed on a quarterly basis for your premium. You must pay this invoice or you will lose your Medicare and your Medicare plan through the City.

Every year in July, the City refunds 50 percent of the amount you paid for your Medicare Part B premium. The refund is issued in your July retirement check for the previous calendar year.

  • For example, the refund issued in July 2016 is for premiums paid from January through December 2015.
  • The City will automatically refund you based on the standard monthly premium amount.
  • If you paid more than the standard premium, you must submit proof of your extra payment no later than April 30th of each year. Proof of payment may be the Social Security 1099 or a letter on Social Security letterhead stating how much you paid.

> Read more information about Medicare Part B Refund

> Download the Medicare Part B IRMAA Refund Request Form

If you are ineligible for Medicare (Part A is not free), you must provide proof. We need a copy of a letter on Social Security letterhead stating that you are not eligible for Medicare Part A for free. You may remain enrolled in a non-Medicare plan.

Family Exemption

If you are covering two or more family members (a spouse and dependents) who are not eligible for Medicare, you may continue coverage in your non-Medicare family plan.

'One Over, One Under'

If you retire and are not eligible for Medicare, but your spouse is eligible:

  • your spouse must enroll in a Medicare plan, and
  • you must enroll in individual coverage in a non-Medicare plan.

If you retire and are eligible for Medicare, but your spouse is not eligible:

  • you must enroll in a Medicare plan, and
  • your spouse must enroll in individual coverage in a non-Medicare plan.

Glossary of Terms

Health Maintenance Organization (HMO) 

A plan that usually limits coverage to care from doctors who contract with the HMO. It generally will not cover out-of-network care except in an emergency. An HMO requires you to live in its service area to be eligible for coverage. HMO plans also require a referral from your primary care doctor to see a specialist.

Value Network HMO

A plan that excludes the highest cost providers, as determined by the health insurance provider, and includes only lower-cost providers that meet a certain quality threshold.

Preferred Provider Organization (PPO)

A plan in which you pay less to use providers that belong to the plan’s network. You can use doctors, hospitals, and providers outside of the network for an additional cost. PPO plans do not require a PCP referral for a specialist visit.

Advanced Imaging:

Diagnostic imaging procedures including magnetic resonance imaging (MRI), computed tomography (CT), and nuclear medicine imaging procedures, such as positron emission tomography (PET).

Annual Enrollment:

The yearly period when employees/retirees can enroll in and change health insurance plans and coverage without a qualifying life event.


A fixed amount you pay for each covered health care service, in addition to your premium and any deductible.


A fixed amount an employee pays for certain services before the insurer begins to pay for those services.  Members pay in full for certain services until reaching the annual maximum deductible amount.

Inpatient Hospital:

Care that you receive when admitted (acute, medical rehabilitation, skilled nursing care). Excludes mental health and substance use disorder.

Outpatient Hospital:

Care that you receive without being admitted or for a stay of less than 24 hours.

Premium Share:

The percent of premium you pay for health insurance every month (from paycheck or pension). The employer pays the remaining percentage.

Primary Care Physician (PCP):

A physician who directly provides or coordinates a range of health care services for a patient.


A physician who focuses on a specific area of medicine or a group of patients to diagnose, manage, prevent, or treat certain types of symptoms and conditions. 

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