The Best Insurance Agencies for Semi Trucks in 2026

From August through October 2026, our research team evaluated 40+ insurance agencies that write coverage for semi trucks across the United States, with an emphasis on agencies headquartered or highly active in the Midwest. We focused on independent agencies and brokerages that represent multiple carriers and act as an intermediary between trucking businesses and the insurers that underwrite their coverage. Each agency was scored using a seven-factor algorithm:

• Year Founded (10%): Agencies with long operating histories have proven they can serve truckers through hard markets, carrier exits, and regulatory change.
• Average Review Score (10%): Client ratings averaged across Google, Trustpilot, the BBB, and other review platforms show how an agency treats truckers after the policy is sold.
• Price Range (8%): Estimated annual premium per semi truck reflects how competitively an agency places coverage for its typical client.
• Awards & Recognition (7%): Industry, carrier, and workplace honors offer third-party validation of an agency’s standing.
• Trucking Specialization (22%): Agencies that write trucking exclusively understand semi truck exposures, filings, and coverage gaps better than generalists that treat trucking as a side line.
• Dedicated Account Service (22%): A named account team that answers calls, issues certificates, and handles mid-term changes keeps trucks moving and protects the carrier when a claim hits.
• Coverage Breadth Across the Fleet Lifecycle (21%): Agencies that can insure a single owner-operator and the same operation later as a multi-state fleet save truckers from switching agencies as they grow.

1. Truck Writers, for Trucking-Only Coverage with a Dedicated Account Team

Founded in Minnesota in 1983, Truck Writers is a family-owned independent agency that writes trucking insurance exclusively. Every client is assigned a dedicated account team, backed by a support staff of 30+ professionals trained to handle certificates, filings, policy changes, and claims without routing truckers through a call center. Because the agency represents multiple insurance carriers, semi truck owners get competing quotes rather than a single carrier’s pricing, and agents build each program from a full review of the operation’s routes, cargo, drivers, and loss history.

The agency’s product depth follows a trucking business through every stage of growth. Coverage lines include auto liability, physical damage, motor truck cargo, workers’ compensation, freight broker insurance, per-trip excess, umbrella, bonds, and captive or self-insurance programs for established fleets. Truck Writers is licensed in 38 states and pairs that reach with hands-on risk management support, helping carriers prevent accidents, control claims costs, and keep premiums down at renewal.

Location: Blaine, MN (additional office in Welcome, MN)

Founded: 1983

Avg. Review Score: 5.0/5.0

Price Range: $$$$$

Services: Auto liability, physical damage, motor truck cargo, workers’ compensation, freight broker insurance, per-trip excess, umbrella, bonds, captive and self-insurance programs

2. Joe Morten & Son, for Legacy Fleet Programs and Carrier Relationships

Joe Morten & Son has served commercial trucking since 1936, making it one of the longest-standing trucking insurance agencies in the country. Founded in South Sioux City, Nebraska, the agency helped establish Great West Casualty Company in 1956 and remains that carrier’s largest agency, serving 9,000+ customers across 46 states from ten service locations. Its Top G.E.A.R. risk management program and captive options, including the PowerTech Elite captive, give well-run fleets a path to long-term loss control.

The agency’s deep ties to a single anchor carrier can narrow the range of competing quotes for some semi truck owners, particularly those whose risk profile does not fit Great West’s appetite. Its business model is built on referrals and long-term relationships rather than a visible digital presence, which leaves prospective clients with little public review data to evaluate. Smaller owner-operators may also find that its consultative fleet programs are designed around larger accounts.

Location: South Sioux City, NE (10 locations nationwide)

Founded: 1936

Avg. Review Score: 4.0/5.0 (averaged across Google listings for its office locations)

Price Range: $$$$

Services: Commercial auto liability, physical damage, cargo, general liability, workers’ compensation, excess liability, owner-operator programs, Top G.E.A.R. risk management, captive programs

3. Cottingham & Butler, for Mid-Size Fleet Captives and Risk Consulting

Cottingham & Butler traces its roots to an 1887 storefront agency in Dubuque, Iowa, and has grown into one of the largest privately held insurance brokers in the United States. Its Transportation Group serves 2,500+ transportation clients and is known for its captive insurance programs, risk management consulting, and an annual Transportation Summit that draws fleet executives from across the country. Transportation accounts for roughly 60% of its commercial lines business.

The agency’s processes are calibrated for mid-size and larger motor carriers, so single-truck owner-operators may find the onboarding heavier than they need. Quote timelines typically run two to five business days, reflecting a thorough underwriting process suited to complex accounts. Trucking also shares the firm’s attention with employee benefits, agribusiness, manufacturing, and construction practices.

Location: Dubuque, IA

Founded: 1887

Avg. Review Score: 4.3/5.0

Price Range: $$$

Services: Auto liability, physical damage, cargo, workers’ compensation, general liability, captive insurance programs, risk management consulting

4. Gallagher, for Large-Scale Transportation Risk Management

Founded in Chicago in 1927, Gallagher is one of the world’s largest insurance brokerage and risk management firms and a Fortune 500 company. Its transportation practice manages more than $1.5 billion in annual premiums across 8,900+ transportation clients and employs 350+ dedicated transportation specialists. Proprietary tools such as Gallagher Drive and CORE360 give large fleets data-driven oversight of their full risk program.

Gallagher’s scale is built for large motor carriers with complex, multi-line programs, and single-truck or small-fleet owners can receive less attention than enterprise accounts. Service quality and response times vary by regional office. Trucking is one practice among dozens at the firm, and minimum premiums for its tailored programs tend to price out smaller operations.

Location: Rolling Meadows, IL

Founded: 1927

Avg. Review Score: 4.5/5.0 (Trustpilot, all business lines)

Price Range: $$

Services: Commercial auto, physical damage, cargo, workers’ compensation, general liability, cyber liability, marine, supply chain coverage

5. Reliance Partners, for Fast-Growing Trucking and Logistics Coverage

Reliance Partners was founded in Chattanooga in 2009 with a focus on the trucking and logistics marketplace. The agency has appeared on the Inc. 5000 list seven years in a row and has grown to 200+ employees across eight locations. Its product set spans auto liability, physical damage, cargo, bobtail, non-trucking liability, excess, workers’ compensation, freight broker coverage, and cross-border programs for carriers running into Canada and Mexico.

Rapid growth has come with uneven client feedback, and its Trustpilot score sits well below the other agencies on this list, with complaints centered on post-claim support and aggressive sales outreach. Its high-volume model can make it harder for semi truck owners to build a lasting relationship with a single account manager. Its headquarters and much of its growth also sit outside the Midwest.

Location: Chattanooga, TN

Founded: 2009

Avg. Review Score: 3.5/5.0 (averaged across Trustpilot and other customer rating platforms)

Price Range: $$$$

Services: Auto liability, physical damage, cargo, bobtail, non-trucking liability, excess, umbrella, workers’ compensation, freight broker insurance, cross-border programs

6. TrueNorth Companies, for Driver-Centric Motor Carrier Programs

TrueNorth Companies was formed in Cedar Rapids, Iowa, in 2001 through the merger of three insurance agencies and has grown to roughly 550 colleagues. Its transportation division won the American Trucking Associations’ Mike Russell Trucking Image Award, and the firm is an ATA corporate partner. Its TNTruck platform helps motor carriers onboard independent contractors and enroll them in coverage paperlessly.

Trucking is one division within a broader firm that also sells employee benefits, personal lines, and financial strategy services. Its transportation programs are designed primarily around motor carriers that lease on owner-operators, rather than independent single-truck operators shopping for their own authority. Public client reviews are limited, which makes service quality harder to verify before signing.

Location: Cedar Rapids, IA

Founded: 2001

Avg. Review Score: 3.9/5.0

Price Range: $$$

Services: Auto liability, physical damage, cargo, workers’ compensation, occupational accident, independent contractor programs, risk management

7. Aronson Group, for Tech-Driven Small Fleet Quotes

Aronson Group was founded in Bettendorf, Iowa, in 2017 with a technology-first approach to trucking insurance. Its proprietary platform automates underwriting workflows and delivers carrier-ready submissions, shortening quote timelines to under 24 hours. The agency works exclusively with 1 to 9 unit trucking companies, serves 5,000+ clients nationwide, and holds a 4.9/5.0 review average, the highest on this list.

Aronson’s exclusive focus on fleets of nine units or fewer means carriers outgrow the agency once they pass that size. Its product set centers on primary auto liability, physical damage, and cargo, with no captive or self-insurance programs for maturing fleets. As a younger agency, it also has a shorter track record through hard insurance markets than legacy agencies.

Location: Bettendorf, IA

Founded: 2017

Avg. Review Score: 4.9/5.0

Price Range: $$$$$

Services: Commercial auto liability, physical damage, motor truck cargo, new venture insurance, flexible policies for changing fleets, FMCSA filings, certificates

8. Lockton, for Complex Large-Fleet Placements

Founded in Kansas City in 1966, Lockton is the world’s largest privately held insurance brokerage. Its Transportation and Logistics Practice dates to the early 1980s and is staffed by 30+ risk management associates in Kansas City who place and service large, complex transportation risks. The practice brings strong claims advocacy, legal resources, and industry affiliations to fleets with significant exposure.

Lockton’s transportation team is explicitly built for large and complex accounts, which puts owner-operators and small fleets outside its core market. Premiums for its custom programs tend to sit at the upper end of the range, and public client reviews are sparse. Trucking is also one practice among many at a firm that operates in more than 140 countries.

Location: Kansas City, MO

Founded: 1966

Avg. Review Score: 3.9/5.0 (averaged across Google listings for its U.S. offices)

Price Range: $

Services: Auto liability, physical damage, cargo, occupational accident, umbrella and excess liability, warehouse legal, workers’ compensation, property

9. Hub International, for Full-Service Multi-Line Brokerage

Hub International is one of the largest independent insurance brokerages in North America, with a transportation division that serves operations from single-truck contractors to large motor carriers. Hub is licensed in all 50 states and across Canada, and it maintains relationships with virtually every national and regional market that writes commercial trucking. Its HUB Drive Online platform and fleet risk management services give larger carriers data tools for reducing accident rates.

Hub’s size and acquisition-driven growth mean service quality varies noticeably by regional office. Trucking is one division within a broker that also sells employee benefits, personal lines, and dozens of commercial specialties, and smaller semi truck owners can find themselves routed through generalist teams. Its review average trails most of the trucking specialists on this list.

Location: Chicago, IL

Founded: 1998

Avg. Review Score: 3.9/5.0

Price Range: $$$

Services: Commercial auto, physical damage, cargo, workers’ compensation, general liability, marine, employee benefits, fleet risk management

The Best Insurance Agencies for Semi Trucks by Specialty

We also broke down the top semi truck insurance agencies into three subcategories based on the size and location of the trucking operation.

The Best Semi Truck Insurance Agencies for Owner-Operators and Small Fleets (1 to 9 Trucks)

1. Truck Writers
2. Aronson Group
3. Reliance Partners
4. Joe Morten & Son
5. TrueNorth Companies

The Best Semi Truck Insurance Agencies for Growing Fleets (10 to 50 Trucks)

1. Truck Writers
2. Joe Morten & Son
3. Cottingham & Butler
4. TrueNorth Companies
5. Reliance Partners

The Best Semi Truck Insurance Agencies for Midwest-Based Carriers

1. Truck Writers
2. Joe Morten & Son
3. Cottingham & Butler
4. TrueNorth Companies
5. Aronson Group

Conclusion

The best insurance agency for a semi truck depends on fleet size, hauling territory, growth plans, and how much hands-on account support the operation needs. The agencies on this list represent the strongest options across that range, from single-truck owner-operators to multi-state motor carriers.

Truck Writers ranked first because of the combination it delivers: more than four decades of trucking-only focus, a dedicated account team for every client, multi-carrier access that keeps pricing competitive, and a product range that covers a trucking business from its first semi to a captive program for a mature fleet. Every agent on staff works exclusively in trucking, so the people handling your policy understand the equipment, the filings, and the stakes when something goes wrong on the road.

Ready to compare coverage for your semi trucks?

Request a quote from Truck Writers and get matched with a dedicated account team today.

Sources

• Truck Writers: About Our Agency
• Truck Writers: Best Trucking Insurance Agencies 2026 Report
• Acuity: Truck Writers celebrates 3 generations
• Cottingham & Butler Transportation Group overview
• Reliance Partners on Trustpilot
• Reliance Partners Inc. 5000 announcement
• TrueNorth wins ATA Image Award
• TrueNorth Companies on Birdeye
• Lockton Transportation & Logistics
• Aronson Group company profile (CB Insights)