Best Trucking Insurance Companies 2026

Best for: Best Overall

Progressive Commercial is the largest commercial auto insurer in the United States, covering everything from single owner-operators to large fleets. Their digital-first approach, competitive quoting engine, and wide range of coverage options make them the go-to for truckers who want a streamlined insurance experience. Progressive writes policies in all 50 states and handles claims through a dedicated commercial team separate from their personal auto division.

Best for: Long-Haul Carriers

Great West Casualty Company has been insuring truckers since 1956 and is one of the most respected names in commercial trucking insurance. Based in South Sioux City, Nebraska, they specialize exclusively in the trucking industry — they don't write personal auto or homeowners policies. This singular focus gives them deep expertise in OTR risk and long-haul operations. Their loss control and safety programs are among the best in the industry, with free driver training resources that can lower your premiums over time.

Best for: Owner-Operators

OOIDA (Owner-Operator Independent Drivers Association) provides insurance programs exclusively for its members — independent owner-operators and small fleet owners. As a member-driven association, OOIDA negotiates group insurance rates that individual truckers could rarely access on their own. Their insurance programs cover occupational accident, physical damage, and non-trucking liability, with additional options for health, dental, and life insurance. The association's advocacy work on behalf of owner-operators means their insurance products are designed with the independent trucker's specific needs in mind.

Best for: Small Fleets

Northland Insurance Company, a Travelers subsidiary, specializes in commercial trucking and transportation insurance for small to mid-size operations. They're known for competitive pricing for fleets of 1-20 trucks and have a streamlined underwriting process that gets small fleet operators covered faster than most competitors. Backed by Travelers' financial strength (one of the largest property-casualty companies in the US), Northland offers the resources of a major carrier with the specialization of a niche insurer.

Best for: Financial Stability

National Indemnity Company is Berkshire Hathaway's flagship insurance subsidiary and one of the most financially stable insurers on the planet. While they're not exclusively a trucking insurer, their commercial auto division writes significant trucking business, and their financial backing means policyholders never have to worry about claims-paying ability. National Indemnity is the parent company of Great West Casualty, and while they operate independently, the Berkshire connection provides unmatched balance sheet strength. They're the right choice for operators who prioritize financial security and long-term stability above all else.

Best for: Fleet Safety Programs

Sentry Insurance has been in business since 1904, making it one of the oldest mutual insurance companies in America. Their trucking division offers comprehensive coverage with an emphasis on loss prevention and fleet safety consulting. Sentry is particularly strong for mid-size fleets (5-50 trucks) where their dedicated risk management team can implement customized safety programs that measurably reduce accident frequency and severity. They operate as a mutual company, meaning policyholders are technically owners, which aligns their interests with keeping losses low.

Best for: New Authority

Canal Insurance Company, headquartered in Greenville, South Carolina, has been insuring commercial trucks since 1939. They've carved out a niche as one of the few established carriers willing to write policies for new authority holders and drivers with limited operating history. While their premiums reflect the higher risk of insuring newer operators, their willingness to provide coverage when others won't makes them an important option in the market. Canal writes through independent agents and focuses heavily on for-hire trucking.

Best for: Heavy Haul

Protective Insurance Corporation (formerly Baldwin & Lyons) has specialized in transportation insurance since 1930. Based in Indianapolis, they're one of the few carriers with deep expertise in heavy haul, oversized loads, and specialized equipment operations. Their underwriters understand the unique risk profile of wide loads, permits, escort requirements, and the specialized equipment used in heavy hauling. While they serve the broader trucking market, their heavy haul expertise is what sets them apart from generalist insurers.

Best for: Quick Online Quotes

CoverWallet, now part of Aon (acquired in 2020), is a digital insurance platform that lets small business owners — including trucking companies — get quotes and purchase coverage online without lengthy phone calls or in-person agent meetings. Their platform aggregates quotes from multiple carriers, presenting options side by side for easy comparison. While CoverWallet isn't trucking-specific, their technology platform is one of the smoothest in the commercial insurance space, and they can connect you with trucking-focused underwriters through Aon's vast carrier network.

Best for: New Carriers

Simplex Group is a trucking services company based in Countryside, Illinois, that bundles insurance with other services like IFTA filing, permits, drug testing, and compliance support. They target new carriers and owner-operators who need a one-stop shop for getting their trucking business off the ground. Simplex works with multiple insurance carriers to place policies for operators that traditional markets may decline, including brand-new authorities and drivers with limited experience. Their bundled approach simplifies the startup process but comes at a cost premium.