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Massachusetts Insurance News & Job Opportunities

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Latest News

Editorial graphic showing a judge’s gavel, law books, and Braintree Town Hall, highlighting a $6.05 million insurance coverage ruling against MIIA arising from a wrongful conviction settlement.

MIIA Ordered To Pay Braintree $6.05M In Wrongful Conviction Case

October 26, 2026

A Massachusetts Superior Court judge rules MIIA must indemnify Braintree for $6.05 million of a wrongful conviction settlement but rejects the Town’s Chapter 93A claim.

Illustration of New England insurance agency mergers and acquisitions slowing in the third quarter of 2026.

New England Agency M&A Down 55% Through Q3 2026

October 26, 2026

New England insurance agency acquisition activity declined 55% during the first nine months of 2026

MountainOne Insurance acquisition of Encharter Insurance Agency in Amherst, Massachusetts

MountainOne Insurance Acquires Encharter Insurance Agency from Plymouth Rock

October 26, 2026

MountainOne Insurance has acquired Amherst-based Encharter Insurance Agency from Plymouth Rock Assurance, effective October 1, 2026. The transaction adds 22 insurance professionals and establishes MountainOne’s first office in Hampshire County.

Illustration of insurance policy documents, attorney fee statements, and a judge's gavel representing a federal ruling awarding legal fees after a coverage denial.

Coverage Denial: Insured Awarded Its Legal Fees

October 26, 2026

A Massachusetts federal judge awarded $99,059 in attorney fees following Mount Vernon’s unsuccessful coverage denial involving a real estate brokerage’s E&O policy. The court also denied the insured’s attempt to add a Chapter 93A claim.

Insurance agency M&A activity declined in the third quarter of 2026

The Freefall in Insurance Agency Mergers & Acquisitions Continues

October 26, 2026

Insurance agency M&A activity is down 40% from the previous five-year average, with 439 acquisitions announced through September 2026, OPTIS reports.

Willis 2027 insurance forecast showing falling commercial property rates and rising auto liability rates, illustrated by a commercial building and trucks.

Insurance Rates in 2027: Property Falls as Auto Liability Rises

October 26, 2026

Willis’s 2027 insurance market forecast points to continued reductions in commercial property rates while auto liability and excess casualty rates rise. The report also identifies improving high-value homeowners insurance conditions in Massachusetts.

CopperPoint acquisition of General Indemnity Group surety insurance business

CopperPoint Completes $84.3 Million Purchase of General Indemnity Group, Former Parent of Quincy-Based UCS

October 26, 2026

Announced earlier this year, CopperPoint Insurance Company has completed its $84.3 million acquisition of General Indemnity Group from Boston Omaha Corporation.

Historical illustration of New England showing a nineteenth-century harbor, antique fire insurance policy, and map of Massachusetts and surrounding states.

Nearly 200 Years Later, These P&C Insurers Still Do Business in Massachusetts

October 19, 2026

Some of Massachusetts’ oldest property and casualty insurers have been in business for nearly 200 years or more. From Norfolk & Dedham and Hingham Mutual to Quincy Mutual, The Andover Companies, and The Hanover, a look at the historic insurers that continue to serve policyholders today.

Insurance Coverage Cases

Editorial graphic showing a judge’s gavel, law books, and Braintree Town Hall, highlighting a $6.05 million insurance coverage ruling against MIIA arising from a wrongful conviction settlement.

MIIA Ordered To Pay Braintree $6.05M In Wrongful Conviction Case

October 26, 2026

A Massachusetts Superior Court judge rules MIIA must indemnify Braintree for $6.05 million of a wrongful conviction settlement but rejects the Town’s Chapter 93A claim.

Illustration of insurance policy documents, attorney fee statements, and a judge's gavel representing a federal ruling awarding legal fees after a coverage denial.

Coverage Denial: Insured Awarded Its Legal Fees

October 26, 2026

A Massachusetts federal judge awarded $99,059 in attorney fees following Mount Vernon’s unsuccessful coverage denial involving a real estate brokerage’s E&O policy. The court also denied the insured’s attempt to add a Chapter 93A claim.

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Latest Agency Sales

Illustration of New England insurance agency mergers and acquisitions slowing in the third quarter of 2026.

New England Agency M&A Down 55% Through Q3 2026

October 26, 2026

MountainOne Insurance acquisition of Encharter Insurance Agency in Amherst, Massachusetts

MountainOne Insurance Acquires Encharter Insurance Agency from Plymouth Rock

October 26, 2026

Insurance agency M&A activity declined in the third quarter of 2026

The Freefall in Insurance Agency Mergers & Acquisitions Continues

October 26, 2026

World Insurance acquisition in Massachusetts

World Insurance Grows Its Presence in Mass. With Hingham Agency Acquisition

September 28, 2026

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DOI News

Massachusetts Auto damage appraiser news

ADALB Moves to Clarify Licensed Appraiser Requirements for Repair Shops

June 20, 2026

Home Insurance Premiums Rose 12.7% During 2024 says Latest DOI Report

February 2, 2026

DOI Issues Consumer Advisory Regarding Roof-Related Insurance Notices

November 6, 2025

DOI Issues Q&A on Protected Accessory Dwelling Units

October 23, 2025

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CAR News

Massachusetts private passenger automobile insurance market share rankings

5th Look 2026: Massachusetts Private Passenger Auto Market Share Report

September 14, 2026 By AC Editor

Massachusetts private passenger automobile insurance market share rankings

4th Look 2026: Look 2026: Market Share Report for MA Auto Insurance Marketplace

July 13, 2026 By AC Editor

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Insurance Fraud

Henry Lam, owner of HL Temporary Services, sentenced in federal workers’ compensation fraud case

Lowell Temp Agency Owner To Do 13 Months for Payroll and Workers’ Comp Fraud

A federal judge sentenced Henry Lam, owner of Lowell-based HL Temporary Services, to 13 months in prison after he pleaded guilty to employment-tax charges and mail fraud involving workers’ compensation insurance premiums.Insuran

Kevin Kolenda prize insurance wire fraud case and Massachusetts insurance ban

Massachusetts Barred His Phony Insurance In 2006. Now Kevin Kolenda Has Pleaded Guilty To Wire Fraud

Nearly 20 years after Massachusetts barred Kevin Kolenda from selling prize insurance without a license, the longtime operator of Hole-in-Won has pleaded guilty to federal wire fraud related to his prize insurance business.

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Ratings & Results

Chubb reported strong second-quarter 2026 earnings while reducing underpriced property business and warning that casualty pricing continues to lag rising loss costs.

Chubb Q2 Net Profit Down 3.8% as Combined Ratio Improves

The Hartford reported strong second-quarter 2026 earnings driven by Business Insurance growth, improved Personal Insurance underwriting, and a new $4.2 billion stock repurchase authorization.

The Hartford Reports Strong Q2 Results as Business Insurance Drives Growth, Personal Lines Profitability Improves

AM Best reports

AM Best Revises Safety Insurance Outlook to Negative, Affirms Ratings

AM Best report showing moderation in auto and homeowners insurance rate increases in 2025

Best’s Special Report: Personal Auto and Homeowners Markets’ Stabilization Evident Despite a Decline in Approved Rate Changes

Arrow Mutual Liability Insurance Company rating downgrade illustration showing AM Best downgrade concept

AM Best Downgrades Arrow Mutual Liability Insurance Company Ratings

Liberty Mutual earnings results

Liberty Mutual Posts $2 Billion Quarter as It Shifts from Defense to Growth

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Economic & Legislative News in Massachusetts

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Regulators Eye In-State Path for Out-of-State Medical Marijuana Patients

October 26, 2026 By State House News Service

Massachusetts cannabis regulators are considering eliminating residency requirements for medical marijuana purchases, a move that could expand access for out-of-state patients as medical sales continue to decline.

Amazon Prime Air drone delivery proposal in Westborough Massachusetts

Lawmakers Want Moratorium on Drone Delivery

October 26, 2026 By State House News Service

Westborough Town Meeting approved a new unmanned-aircraft bylaw in response to Amazon Prime Air’s proposed drone delivery operation, while Massachusetts lawmakers seek a temporary moratorium on commercial drone applications.

Massachusetts wrong-way driving detection system on a state highway

Wrong-Way Driving Systems Have Recorded More Than 215 Events Since June

October 26, 2026 By State House News Service

MassDOT says its wrong-way driving detection systems have recorded more than 215 events since June, with about 140 drivers correcting course after alerts.

Massachusetts added 3,500 jobs in September 2026 while unemployment held at 4.3%

Mass. Gained Jobs in September, but Unemployment Rate Held at 4.3%

October 19, 2026 By State House News Service

Massachusetts added 3,500 jobs in September while the unemployment rate remained at 4.3% and the state labor force increased by 8,400, according to preliminary state data.

Massachusetts business confidence index rose to 48.6 in September 2026

Business Confidence Held in Negative Territory in September

October 5, 2026 By State House News Service

Massachusetts business confidence improved in September, with the Associated Industries of Massachusetts index rising 1.2 points to 48.6, though sentiment remained in negative territory.

MBTA bus camera enforcement program in Massachusetts

Limited Bus Camera Pilot Found 26,000 Violations

September 29, 2026 By State House News Service

The MBTA says an automated camera enforcement pilot on four buses captured 26,000 bus stop and bus lane violations during a 30-day test as the agency prepares for broader enforcement in 2027.

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New England Newswire

Vehicle theft declines in Vermont and New Hampshire during the first half of 2026

Vehicle Thefts Fall 21% Nationwide; Vermont, New Hampshire Among Biggest Declines

October 5, 2026 By AC Editor

New Hampshire Insurance Department Issues Bulletin on Auto Policy Termination for Nonpayment at Renewal

September 14, 2026 By AC Editor

Arbella Insurance Group's commercial lines office in Bedford, New Hampshire.

Arbella Opens First Commercial Lines Office in New Hampshire

August 31, 2026 By AC Editor

New Hampshire Insurance Department fiscal 2026 results

New Hampshire Insurance Department Contributes $189.2 Million To State General Fund

August 10, 2026 By AC Editor

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Company Newswire

Arbella employees support Dana-Farber during the insurer’s 18th annual Pink Day

Arbella Marks 18th Annual “Pink Day” in Support of Dana-Farber Cancer Institute

Arbella Insurance Group employees and the Arbella Insurance Foundation raised $65,000 for Dana-Farber Cancer Institute during the company’s 18th annual Pink Day.

SIAA acquisition of specialty MGA Canopy Specialty Insurance

SIAA Acquires Canopy Specialty Insurance, Expanding Specialty Underwriting Capabilities

SIAA has acquired Canopy Specialty Insurance, a U.S.-U.K. specialty commercial P&C managing general agent, adding underwriting and product development capabilities to its distribution platform.

MountainOne Insurance earns MAIA Five Star Agency Designation

MountainOne Insurance Becomes 15th Massachusetts Agency With MAIA Five Star Designation

MountainOne Insurance has earned the Massachusetts Association of Insurance Agents’ Five Star Agency Designation, becoming the 15th agency in the state to hold the recognition.

The winner of the MAIW/Essex Chapter Scholarship for 2026

The Winners Of The MAIW’s Essex/Middlesex Chapter 2026 Estelle Jeter Scholarship

This is the 88th year of operation for the Massachusetts Association of Insurance Women.

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Primary Sidebar

  • NEW! BOSTON: Product Management Analyst (Safety)
  • NEW! DEDHAM: Senior Commercial Lines Underwriter (N&D)
  • WOBURN: Director of Finance – Insurance Services (Salem Five)
  • SOUTHBOROUGH: Agency Development Representative (HMIC)
  • YARMOUTH: Employee Benefits Producer – Division Manager (Pioneer Insurance Partners)

Career News

Staff Boom Strengthens Executive Leadership Team to Accelerate Technology-Led Growth

Lou Garcia, president and CEO of InsurBanc

Lou Garcia joins InsurBanc as President and CEO

Jared Stuckey, vice president of customer service and underwriting at Plymouth Rock Home Assurance

Plymouth Rock Home Assurance Names Jared Stuckey VP of Customer Service and Underwriting 

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Interviews

From Nuptials, Tickets, and Taxes to Trusted Advisor: One Agency’s Unique Path to P&C Success

A Conversation with Evan Silverio, President & CEO of Silverio Insurance Group

Deland, Gibson Celebrates 125 Years: A Conversation with CEO Chip Gibson

The Fourth-Generation Family-Owned Agency is Based in Wellesley

Talking with Richard Welch: Growth and Innovation at Hospitality Mutual | Agency Checklists

Talking with Richard Welch: Growth and Innovation at Hospitality Mutual

Mr. Welch is CEO of Massachusetts-based Hospitality Insurance Group

Born and Bred in the Bay State: The Special Agent Story

Our Latest Agency Interview is with the Founder & President of Special Agent

A Conversation with Daniel C. Bridge – The 2023 Insurance Professional of the Year

Daniel Bridge is Board Chair, President, and CEO of Vermont Mutual Insurance Group

Making The Leap From Corporate to Entrepreneur: Nadeen Vella On Building NaVella Insurance From Scratch

Making The Leap From Corporate to Entrepreneur: Nadeen Vella On Building NaVella Insurance From Scratch

Our latest Agency Interview is with Nadeen Vella, the founder and owner of a virtual scratch independent agency.

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MA Division of Insurance Announcements

In Memoriam

In Memoriam: James P. Daley, 1959-2026

In Memoriam: Richard Sias, 1946-2026

In Memoriam: Stephen Joel Paris, 1938-2026

InsurOp-Eds

Agency Checklists, MA Insurance News, Mass. Insurance News, Insurance Claims, How to make an insurance claim after a natural disaster

The REAL Customer Experience

By Bill Wilson

Agency Checklists, MA Insurance News, Mass. Insurance News, Insurance Claims, How to make an insurance claim after a natural disaster

InSurOp-Ed: An Agent Call To Action: Underinsurance

By Bill Wilson

How Agents Can Ensure Home Improvement Projects Are Reflected Properly Within Their Clients’ Homeowners Policies

By Jim Hyatt

Massachusetts Auto damage appraiser news

InsurOp-Ed: My First Auto Claim In 50 Years

By Bill Wilson

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