The 2027 Open Enrollment is October 23, 2026, through January 23, 2027.

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
October 23, 2026 November 1, 2026
November 23, 2026 December 1, 2026
December 23, 2026 January 1, 2027
January 23, 2027 February 1, 2027
February 23, 2027 March 1, 2027
March 23, 2027 April 1, 2027
April 23, 2027 May 1, 2027
May 23, 2027 June 1, 2027
June 23, 2027 July 1, 2027
July 23, 2027 August 1, 2027
August 23, 2027 September 1, 2027
September 23, 2027 October 1, 2027
October 23, 2027 November 1, 2027
November 23, 2027 December 1, 2027
December 23, 2027 January 1, 2028

If you are applying and enrolling in a health or dental 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.
Last Update: October 23, 2026
General Information, Individuals & Families, Students