Playbook: Risk & Insurance

Rob Carpenter Tuesday, February 24, 2026

A handful of parent companies control America’s trucking insurance market

The seventh installment in FreightWaves’ investigation into America’s trucking insurance crisis reveals that the apparent diversity of the commercial truck insurance market is an illusion. Behind dozens of subsidiary names filing BMC-91s with FMCSA sit a small number of Fortune 500 holding companies. The concentration of risk is worse than anyone in the industry realizes.

Read More »
Rob Carpenter Friday, February 13, 2026

Trucking Risk Control Could Become the New Entrant Gate

For decades, insurance was the one thing you couldn’t fake your way past to start a trucking company. That’s no longer true. As instant-issue coverage and $300 authority fees make it easier than ever to place 80,000 pounds on public highways without verification, a scalable, pre-authority risk-control model could restore the gate the industry lost without adding a single federal employee to the payroll.

Read More »
Rob Carpenter Thursday, February 12, 2026

Inside the Shadow Market: 200,000+ Trucking Crashes Without Guaranty Fund Protection

My investigation found 76 Risk Retention Groups insure nearly 30,000 motor carriers linked to more than 6,300 fatal crashes, all without state guaranty fund protection for crash victims. The findings come as reports indicate that major insurers, including Chubb and AmTrust, are exiting the Chicago trucking market, funneling high-risk carriers into RRGs that have already incurred $199 million in unpaid losses and multiple insolvencies.

Read More »
Rob Carpenter Thursday, January 29, 2026

The $75,000 Bond and Truckers Left Holding The Bag

Nearly 88,000 trucking companies closed in 2023. Fraud losses topped $455 million in 2024. Carriers filing claims against $75,000 surety bonds are discovering that the pot’s already been split 50 ways. As the Supreme Court prepares to rule on whether brokers can be held liable for hiring bad carriers, it’s time to ask: who really bears the risk in freight, and is the system rigged against the people actually moving the loads?

Read More »
Rob Carpenter Tuesday, January 20, 2026

Why Robotaxis Keep Failing While AV Trucks Take the Slow Road to Safety

In December 2025, Waymo recalled 3,067 robotaxis after its vehicles ran red lights and blew through school bus stop signs at least 20 times in Austin alone, including one incident that occurred moments after a child crossed in front of a vehicle. Meanwhile, Aurora’s autonomous trucks have completed over 100,000 driverless miles in Texas without a single school bus incident. The difference is methodology, and understanding that difference might just save your life.

Read More »
Rob Carpenter Friday, January 16, 2026

The Stagecoach Robbing Era and The Evolution of Freight Fraud

The freight industry moved $14 trillion in goods last year. It cannot function without trust, trust that the carrier picking up your load is who they claim to be, trust that the broker paying you will actually pay, and trust that the load you accepted exists. That trust has been systematically exploited for decades. At its root, every form of freight fraud, chameleon carriers, double brokering, cargo theft, identity spoofing, comes down to one question: Are you who you say you are?

Read More »
Rob Carpenter Monday, January 12, 2026

Trucker Charged in Fatal I-81 Crash Released on Bond as Questions Swirl Over Crash Transparency

When a commercial vehicle operator is charged with killing three people and walks out of jail on bond following a hearing that doesn’t appear on the public court docket, questions need to be asked. El Hadji Karamoko Ouattara’s January 7 bond hearing is on the docket, but after nearly three weeks since the crash, no one has identified the motor carrier he was hauling for.

Read More »
Rob Carpenter Tuesday, April 15, 2025

Fleets Face Privacy Challenges as Workplace Surveillance Looks at Major Overhaul

A proposed California law, Assembly Bill 1331, could upend how trucking fleets monitor drivers by prohibiting dashcam and GPS surveillance during off-duty periods, even inside the vehicle. If passed, the bill would redefine off-duty time as private, creating costly compliance challenges and raising concerns about safety, theft prevention, and liability. With $500 penalties per violation and the potential for lawsuits, fleets operating in California, and nationwide, may need to rethink how they balance privacy with operational oversight.

Read More »
Rob Carpenter Tuesday, April 8, 2025

Fleets Face Privacy Challenges as Workplace Surveillance Looks at Major Overhaul

A proposed California law, Assembly Bill 1331, could upend how trucking fleets monitor drivers by prohibiting dashcam and GPS surveillance during off-duty periods, even inside the vehicle. If passed, the bill would redefine off-duty time as private, creating costly compliance challenges and raising concerns about safety, theft prevention, and liability. With $500 penalties per violation and the potential for lawsuits, fleets operating in California, and nationwide, may need to rethink how they balance privacy with operational oversight.

Read More »
Rob Carpenter Monday, February 17, 2025

Fighting Back Against Truck Accident Fraud and Why Visibility Matters

The trucking industry is under attack from rising insurance costs, cargo theft, and nuclear verdicts. Now, fraudulent staged accidents have emerged as another costly threat, orchestrated by criminal networks to exploit insurance claims and extract massive settlements. Cases like “Operation Sideswipe” in New Orleans and similar schemes in New York have cost the industry hundreds of millions of dollars.

Adding to the crisis is third-party litigation financing (TPLF), where private investors bankroll lawsuits, driving up the frequency of multi-million-dollar verdicts against carriers. However, fleets are fighting back with AI-powered dashcams from companies like Motive, providing real-time visibility, GPS tracking, and data-backed defenses against fraudulent claims.

This article talks about how dashcams are shifting the landscape, preventing staged accidents, disproving false liability claims, and helping carriers build defensible compliance programs. Read on to learn how visibility, data, and technology can protect your fleet from fraud and exposure.

Read More »