The 2026 Open Enrollment period ended January 23, 2026. The 2027 Open Enrollment starts November 1, 2026.

In general, Open Enrollment is the only time of year when you can purchase or change insurance plans for any reason. However, you may be allowed to enroll at any time of year if you experience certain life events, such as losing your current insurance. If you qualify for MassHealth, or for a ConnectorCare plan, or want to purchase a standalone dental plan, you may enroll at any time during the year. Find out more now →

When you enroll in a health or dental plan by the enrollment deadline – which is the 23rd day of each month – then the earliest plan start date is the first day of the following month. For example, if you complete enrollment by September 23, then your coverage start date will be October 1.

Monthly Plan Selection and Payment Deadlines

Payment Due Date Coverage Start Date
December 23, 2025 January 1, 2026
January 23, 2026 February 1, 2026
February 23, 2026 March 1, 2026
March 23, 2026 April 1, 2026
April 23, 2026 May 1, 2026
May 23, 2026 June 1, 2026
June 23, 2026 July 1, 2026
July 23, 2026 August 1, 2026
August 23, 2026 September 1, 2026
September 23, 2026 October 1, 2026
October 23, 2026 November 1, 2026
November 23, 2026 December 1, 2026
December 23, 2026 January 1, 2027

If you are applying and enrolling in a Health Connector or ConnectorCare plan for the first time, your enrollment isn't finished until you checkout your plan and make your first premium payment for your coverage by the due date. If you miss this deadline, the earliest date your coverage could start is the first day of the following month.