3 Trucking Insurance Options to Consider
While some insurance will always be dictated by regulations (like liability insurance) or shipper demands (cargo insurance), other choices are driven by unique business needs and concerns. Here are three examples.

Halvor Lines' Chief Risk Officer Adam Lang, right, with Halvor CEO Jon Vinje and insurance representative Chad Hoppenjan from Cottingham and Butler, posing for a promotional photo for Halvor’s insurance captive pre-COVID.
Photo: Halvor Lines
Insurance is one of the few products you buy in the hopes that it’s never used. But when disaster strikes, an appropriate level of coverage can define the difference between a speedy recovery and economic ruin.
While some coverage will always be dictated by regulations (like commercial auto liability insurance) or individual shipper demands (cargo insurance), other choices are driven by unique business needs and concerns. Here are three examples that might deserve a closer look by trucking operations.
1. Cyber Security Coverage
Trucking companies are increasingly becoming the victims of cyberattacks, including the ransomware that requires payment in exchange for unlocking digital files. Even the FBI has issued a warning about hackers tapping into vulnerable ELDs.
It’s more than an inconvenience. Depending on the files that are locked away, the business of assigning loads can come to a screeching halt. Worse yet, personal information can be stolen, sold, and repurposed for other criminal activities.
“Nearly every fleet office and every vehicle these days is connected, and every connecting point is a point of sale for a hacker,” says Vishal Kundi, CEO of Boxx Insurance. Every connected device a driver brings to work introduces another vulnerable digital path.
To compound matters, hackers are not always the professionals who lurk under the cover of the dark web. The fastest-growing segment of attackers are rogue employees, he says. Maybe they were put on furlough, or feel disaffected with the company
“It’s not the hack that’s what will kill your business. It’s how you manage it,” Kundi says. “You may pay, but not get the data back.”
One of the challenges is that there’s no standard form of cyber insurance. “Will it pay for the ransom, or will it pay just for the recovery of the data?” Kundi says, referring to one key question.
The level of required coverage will depend on the business, too.“How many client records or employee records do you have?” Kundi asks, noting that it can cost $200 to $300 to address each record lost in a privacy breach. The costs involve everything from notifying customers and regulators, to rebuilding the records themselves.
“Truckers have a ton of employee information, and they’ve got a ton of contract information for part-time drivers.”
Add the costs of business interruption to that, and it explains why many smaller Boxx customers are still securing between $1 million and $5 million in coverage.
2. Enhanced Disability Coverage
When owner-operators are told they need to purchase private disability coverage, Glenn Caldwell knows they usually focus on two topics: How much it costs, and how much it will pay in the event of an injury. But Caldwell, vice-president – corporate development at NAL Insurance, says another key consideration will be the “exclusions” that determine which medical conditions and situations will not be covered.
“Do the research and implement a plan that’s going to fully be there,” he says. “Sadly, many times a fleet doesn’t find out until after a claim hits the auto policy that the program [an owner-operator] accepted has limitations.”
It’s also easier to make the case for an extra $5 or $10 a month than to ask for an extra $200 a month after a major motor vehicle accident injury claim hits the auto policy, Caldwell adds.
It’s all about reading the fine print. Insurers approach topics like “pre-existing” medical conditions in different ways. A change in blood pressure medication, for example, might be the only thing needed to deny coverage for a heart attack that occurs on the road in the U.S.
“Some of the higher-value benefit plans cover all stable pre-existing conditions as long as a doctor hasn’t said you can’t travel or there’s something underlying there,” Caldwell says. “It’s always about asking the questions.”
The level of payments can vary dramatically, too. A cheaper plan might cap payments for physiotherapy sessions at $30 per visit. Those won’t make much of a dent in a bill that approaches $800.
In terms of securing accident disability coverage, Caldwell recommends looking for features such as first-day accident disability, meaning there’s no waiting or elimination period. Benefits should also be paid based on gross earnings rather than net, and apply 60 days per injury in the case of strains and sprains, he adds.
“Read your policy. Make sure you understand. If you don’t, make sure you speak to your broker.”
3. An Insurance Captive
One strategy to help control insurance-related costs but still secure the appropriate coverage is to join an insurance captive – an insurance company owned and controlled by a group of fleets. It presents the added potential of sharing in dividends as well.
Coverage like this isn’t meant to protect against the massive liability-related losses that follow so-called nuclear verdicts, but it can offer the protective layer to address the smaller losses that are relatively common in trucking – such as physical damage and property damage.
While traditionally limited to larger fleets, or even businesses large enough to form their own captive, interest has expanded among mid-sized fleets, says Avi Goldberg, a transportation insurance broker at Marsh Canada.
One of the reasons for that growing interest is today’s “hard” market, as costs increase and some insurance providers reconsider whether they’re even interested in underwriting certain types of business in the first place.
“There’s not a lot of excess liability carriers in the market for transportation,” Goldberg says as an example, referring to the coverage used to build up limits on top of an original policy, closing gaps in coverage and offering fleets some added protection. “If you want $5 million or $10 million liability limits, it’s very difficult.”
But insurers can be enticed by companies that join together.
Every captive sets the requirements for those who are allowed to join. The 20 members in a captive managed by Marsh Canada, for example, demonstrate a commitment to risk management. “So we have certain standards and certain conditions that the members put together.”
Given that one fleet’s losses will affect the prices paid by other businesses within the captive, there’s a greater interest in sharing best practices. Outside a captive, fleets might keep information about everything from mileage to losses under wraps, he explains. “They compete against each other. They price against each other.”
But knowing such details can lead to a safer operation and fewer losses. It’s why a safety group within the Marsh-managed captive meets twice a year. Rather than leaving decisions to a single risk manager, fleets can tap into the insights of 20 peers.
Each captive’s structure is ultimately dictated by its members, so any review should consider obligations as well as the coverage. There will be unique requirements concerning collateral that needs to be presented, as well as exit conditions.
The costs are not limited to premiums alone, either. Captive members purchase shares as a price of membership. There may also be an expectation of topping up the funds if premiums are exhausted.
Any captive that doesn’t incorporate a cap of some sort is a risky proposition for everyone involved, he adds, providing another reason to read the fine print and any re-insurance agreements.
Expect the type of coverage to grow along with the interest in the entities themselves. Goldberg expects captives to expand into areas such as employee benefits and business interruption insurance.
It’s all about ensuring everyone is well covered.
John G. Smith is the editorial director of Newcom Media's trucking and supply chain publications – including Today's Trucking, trucknews.com, and others. A version of this article first appeared on trucknews.com and was used with permission from Newcom Media as part of a cooperative editorial agreement.
More Safety & Compliance

Brake Safety Week to Focus on Drums and Rotors
Commercial vehicle inspectors will be focusing on brakes during CVSA's Brake Safety Week, August 23-29.
Read More →
Trump Administration Looks to Put More Veterans Behind the Wheel
The Freedom Haulers program pulls together existing and expanded programs at several federal agencies to recruit veterans to drive commercial heavy-duty trucks and cut the red tape for them to get a CDL, training, and employment.
Read More →
$604 Million Verdict Tests Broker Liability After Supreme Court Ruling
C.H. Robinson plans to appeal after a Texas jury found it bore the largest share of responsibility for a fatal 2021 crash, in a case that follows the Supreme Court's Montgomery decision allowing negligent hiring claims against freight brokers.
Read More →
How Fraley & Schilling Improved Logbook Compliance by Over 50%
Fraley & Schilling needed a way to close a compliance workflow gap in its ELD system without adding more work from driver training, reminders, and back-office follow-ups. It found the answer in a custom driver app.
Read More →
Farewell, CDL: Why I'm Giving Up My Commercial Driver's License
After more than 20 years as a CDL holder, HDT Executive Editor Jack Roberts is letting his commercial license expire. Not because he wants to — but because trucking's nuclear verdict crisis has made the risks of public-road test drives too great for editors, manufacturers, and everyone involved.
Read More →
Enhance Fleet Performance with High-Efficiency Auxiliary Power Units
Drive sustainable cost savings while increasing driver comfort during short- and long-haul logistics operations.
Read More →
Wabash Trailers Recalled for Improperly Installed Underride Guards
More than 900 Wabash dry van trailers may not comply with the Federal Motor Vehicle Safety Standard for rear impact guards.
Read More →
Why K&B Trucking Is Embracing AI and Driver Safety Technology
Crunching data and embracing artificial intelligence are key in K&B Trucking's safety efforts, says the company's safety director.
Read More →
The Hidden Problem Behind FMCSA's ELD Revocations
NMFTA researchers say dozens of registered ELDs may be built on the same software platforms, allowing compliance and security concerns to persist even after individual devices are removed from the market.
Read More →
ATRI Wants Motor Carriers for Driver-Facing Camera Study
In this new study, the American Transportation Research Institute will explore how driver-facing cameras can impact safety and operational metrics in trucking fleets.
Read More →
