Healthcare for Business
2026 Massachusetts Application timelines
Below are the deadlines for applying, enrolling and submitting first payment for your businesses healthcare benefits in Massachusetts.
It’s recommend to a quote at least 30 days prior to your coverage start date.
March 1st, 2026
Employer Application Deadline: February 1st, 2026
Employee Enrollment Deadline: February 10th, 2026
First Payment Due: February 20th, 2026
April 1st, 2026
Employer Application Deadline: March 1st, 2026
Employee Enrollment Deadline: March 10th, 2026
First Payment Due: March 20th, 2026
May 1st, 2026
Employer Application Deadline: April 1st, 2026
Employee Enrollment Deadline: April 10th, 2026
First Payment Due: April 20th, 2026
June 1st, 2026
Employer Application Deadline: May 1st, 2026
Employee Enrollment Deadline: May 10th, 2026
First Payment Due: May 20th, 2026
July 1st, 2026
Employer Application Deadline: June 1st, 2026
Employee Enrollment Deadline: June 10th, 2026
First Payment Due: June 20th, 2026
August 1st, 2026
Employer Application Deadline: July 1st, 2026
Employee Enrollment Deadline: July 10th, 2026
First Payment Due: July 20th, 2026
September 1st, 2026
Employer Application Deadline: August 1st, 2026
Employee Enrollment Deadline: August 10th, 2026
First Payment Due: August 20th, 2026
October 1st, 2026
Employer Application Deadline: September 1st, 2026
Employee Enrollment Deadline: September 10th, 2026
First Payment Due: September 20th, 2026
November 1st, 2026
Employer Application Deadline: October 1st, 2026
Employee Enrollment Deadline: October 10th, 2026
First Payment Due: October 20th, 2026
December 1st, 2026
Employer Application Deadline: November 1st, 2026
Employee Enrollment Deadline: November 10th, 2026
First Payment Due: November 20th, 2026
What MedHealth has to offer:
Access to 50+ plans offered through 5 top insurance companies and 3 different plan types through the Massachusetts Health Connector for small businesses.
Savings opportunities for qualified businesses, like saving 15% through ConnectWell and up to 50% health care tax rebates.
Personalized service to help navigate policy renewals, onboarding employees and other administrative tasks.
Tell us more about your business
Access Health & Dental Plans
Proud Partner of the
Servicing Businesses Across Massachusetts
Call or Text (617) 515-7291
Frequently Asked Question
Working with us is completely FREE to small businesses, we are compensated by insurance companies. We help our partners in several different ways.
Finding the right plan - We learn about your company, employees, goals and budget to find the best plan for your busienss.
Service - We help employees enroll in your plan, answer their questions and manage events like adding dependents due to the birth of a child. Plus, we work hard to find you tax rebates or state approve rebates.
Renewals - We communicate important renewal date, coordinate documents and cover plan changes.
Here's what you need to qualify to obtain coverage through the Massachusetts Health Connector.
Your company has between 2-50 employees.
Your company is based in Massachusetts.
Plan Options - select from over 50 plan options across 3 plan types, we'll help you find the right one.
Savings - On top of the many options, there are cost savings and tax rebated available to qualified businesses.
Simplicity - The platform brings together big insurance companies, the State of Mass and certified brokers, like MedHealth to provide an easy health coverage experience.