Massachusetts drivers can apply for the RMV’s 2026 Low Number License Plate Lottery through Aug. 14. The lottery will award 237 coveted passenger plates.
Main Content

4th Look 2026: Look 2026: Market Share Report for MA Auto Insurance Marketplace
Agency Checklists analyzes April 2026 CAR data, ranking Massachusetts private passenger auto insurers by market share, exposures, and market concentration.

4th Look 2026: Market Share Report for MA Commercial Auto Insurers
Safety, Commerce and Arbella lead the Massachusetts commercial auto insurance market. See market share rankings, premiums, and carrier concentration.

Insurify Surpasses 250 Million Auto Insurance Quotes
Cambridge-based Insurify has surpassed 250 million real-time auto insurance quotes, expanding its online comparison platform and consumer insurance data.

Boston Last For Second Year In Allstate’s Best Driver Report
Boston ranked last among the nation’s 200 largest cities in Allstate’s 2026 Best Drivers Report, with Worcester and Springfield also ranking among the bottom five.

Grand Jury Indicts In $585K Workers’ Comp Fraud Scheme
Roof Kings owner Craig Galligan and his company were indicted on workers’ compensation fraud charges alleging nearly $585,000 in unpaid insurance premiums
Governor Healey Appoints Nick Fyntrilakis to Massachusetts Convention Center Authority Board
Governor Healey appointed MAIA President and CEO Nick Fyntrilakis to the Massachusetts Convention Center Authority Board, representing Hampden County.

Vermont Mutual To Reorganize As Mutual Holding Company
Vermont Mutual is seeking policyholder approval to reorganize into a mutual holding company while preserving mutual ownership and independent agency distribution.
Insurance Coverage Cases

Appeals Court Redefines “Contractual Relationship” Under Public Bond Statute
Mass. Appeals Court rules third-party beneficiary rights create a “contractual relationship,” avoiding Section 29’s 65-day bond notice requirement.

Court Rules: ‘Regardless of Whether’ In Exclusion Creates Ambiguity
A Massachusetts Federal court finds insurer must defend Vineyard hangar operator after $1.45M propeller damage claim.
Latest Agency Sales

King Risk Partners Expands Massachusetts Presence with Acquisition of Perry Insurance Agency

SIAA-affiliated Sequel Insurance Agencies Acquires Five Independent Agencies

World Welcomes Worcester’s Wolpert Insurance

Springfield’s Honor Capital and Ascend Announce Agreement to Merge
Insurance Fraud

Grand Jury Indicts In $585K Workers’ Comp Fraud Scheme
Roof Kings owner Craig Galligan and his company were indicted on workers’ compensation fraud charges alleging nearly $585,000 in unpaid insurance premiums

Contractor Indicted For Comp Fraud On Sub Misreps
A Milford contractor was indicted on workers’ comp. insurance fraud charges on allegations that roofing work was misclassified to reduce insurance premiums.
Ratings & Results

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

AM Best Downgrades Arrow Mutual Liability Insurance Company Ratings

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

$14.3M Q1 Loss For Safety: Back-To-Back Storms’ 1600 Claims Cost $42.7M

Record Q1 Results: The Hanover’s Combined Ratio Improves to 91.7%

Vermont Mutual Annual Meeting Shows Strong Results
New England Newswire

Vermont Mutual To Reorganize As Mutual Holding Company

Lemonade Launches Renters Insurance in Vermont With Rates Starting at $5 Per Month
By AC Editor

New Hampshire Insurance Department Monitoring NAIC Security Incident
By AC Editor

Connecticut Named Captive Domicile of the Year at Captive Review Awards USA 2026
Economic & Legislative News in Massachusetts

Health Insurers Say Drug Costs, Patient Expectations Tightening Cost Bind
Massachusetts insurers propose average 12.9% premium increases for 2027, citing specialty drug costs and rising provider reimbursement rates.

Report Flags Insurance Woes for Security, Airport Service Workers
New report finds many union security and airport workers lack affordable health coverage, with high uninsured rates despite employer-sponsored plans.

Poll: Fewer Parents Expect Their Kids to Pursue Bachelor’s Degree
New polling shows declining interest in four-year degrees among Massachusetts students, with sharp gaps by income, race, and parental education.

Annual Sales Tax Holiday Set for Weekend of Aug. 8-9
Massachusetts will hold its 2026 sales tax holiday Aug. 8–9, suspending the 6.25% tax on most purchases under $2,500.

Healey Throws Support Behind Happy Hour in Pursuit of ‘Vibrancy’
Gov. Healey backs happy hour and extended last call as Massachusetts tests new nightlife policies aimed at boosting business and retaining young residents.

Court Rejects Bid to Derail Marijuana Ballot Question
Massachusetts SJC rules AG’s summary fair and allows marijuana repeal ballot question to advance toward the November election.
Company Newswire

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.

Arbella Insurance Foundation Raises Over $214,000 for Hunger Relief Programs Across New England
Arbella Insurance Foundation raises $214K for hunger relief, supporting 120 food programs across New England amid rising food insecurity.
MassMutual turns 175, Marking Generations of Delivering on its Commitments
MassMutual marks its 175th anniversary, highlighting policyholder focus, $1T in coverage, and a legacy of dividends and community support.

FM and Disney Relaunch ‘Disney Wild About Safety,’ Presented by FM
FM and Disney relaunch the Wild About Safety program, expanding global safety education through updated content and enhanced storytelling.








