---
title: "Free Help for Boston Residents as Health Insurance Sign-Ups Open"
url: https://www.hereboston.com/2026/10/24/boston-health-insurance-open-enrollment-free-help/
date: 2026-10-24T06:53:18-04:00
modified: 2026-10-24T06:53:18-04:00
author: "Connor Rendon"
categories: ["Health"]
site: "HERE Boston"
attribution: "HERE Boston"
---

# Free Help for Boston Residents as Health Insurance Sign-Ups Open

> BOSTON, Mass. — The window to shop for 2027 health coverage through the Massachusetts Health Connector opened on Friday, Oct. 23, and Boston officials are urging residents to use free city help to pick a plan. Sign-ups stay open until Jan. 23, 2027. Anyone who wants a plan to start on New Year's Day has

*Source: [HERE Boston](https://www.hereboston.com/2026/10/24/boston-health-insurance-open-enrollment-free-help/) — October 24, 2026 by Connor Rendon*

BOSTON, Mass. — The window to shop for 2027 health coverage through the Massachusetts Health Connector opened on Friday, Oct. 23, and Boston officials are urging residents to use free city help to pick a plan.

Sign-ups stay open until Jan. 23, 2027. Anyone who wants a plan to start on New Year’s Day has to finish by Dec. 23; people who sign up after that, through the January deadline, will see coverage begin Feb. 1.

In Boston, the Mayor’s Health Line, run by the Boston Public Health Commission, has trained staff who walk people through Connector applications at no cost and in confidence. Staff can assist in Spanish, Portuguese, both Haitian and Cape Verdean Creole, and English, while an interpreter service covers other languages. Residents can book a phone appointment at 617-534-5050, and the line plans walk-in help sessions at the City Hall Pavilion.

Mayor Michelle Wu said federal changes have made getting covered more confusing and that the city wants every resident to keep a plan or find a new one. The health line can also help MassHealth members who could lose benefits under new federal Medicaid work rules for some adults ages 19 to 64.

Gov. Maura Healey launched the season at an event in Roxbury alongside Boston Public Health Commissioner Dr. Bisola Ojikutu. The state is again putting in extra money after federal enhanced premium tax credits ran out, so about 279,000 ConnectorCare members should see little or no premium increase next year. Statewide, Navigators offer free sign-up help at 50 sites in 29 languages, and plans can be compared at MAhealthconnector.org or by calling 1-877-623-6765.