Mutual insurer in Stevens Point, WI with a transportation unit writing auto liability, physical damage, cargo, non-trucking and general liability through trucking-focused appointed agencies.
Services
Who it serves
Overview
Sentry Insurance is a mutual insurance company based in Stevens Point, Wisconsin, founded in 1904. It is an insurance carrier (underwriter) with several business units, including a dedicated transportation unit that insures trucking companies. Sentry says it insures more than 50,000 truck drivers.
Sentry has been an American Trucking Associations Featured Product provider for eight consecutive years and is an allied member of the ATA and other trucking associations. Its trucking insurance is sold only through appointed agencies that specialize in trucking.
Compare with other Insurance providers: Cottingham & Butler, Roanoke Insurance Group and Progressive Commercial, or see all Insurance.
Services
Sentry's trucking page lists commercial auto liability, physical damage (covering damage from weather, animals or other drivers), motor truck cargo (covering loss from destruction, theft and similar events), non-trucking liability for owner-operators driving for personal use, general liability with product liability, product recall and E&O options, and cyber liability for data breach risks.
Its motor carrier page also mentions coverage for employees using rented vehicles for company business, loss of use expenses after a company vehicle is stolen, and loss of personal effects in a stolen vehicle.
On the safety side, Sentry has transportation safety services staff who help customers identify risks and set up safety procedures, and its trucking page says its safety directors have more than 20 years of industry experience. It publishes trucking resources on coverage, safety and retirement planning, plus a workers compensation guide.
Sentry offers a telematics program through TruckerCloud. Its site says insureds may earn a premium discount at bind by sharing telematics data. Claims are handled in-house by Sentry adjusters who specialize in trucking risks, rather than being outsourced.
Who it is for
Sentry says it serves both owner-operators and large fleets, though it does not publish fleet size thresholds. Its non-trucking liability product is aimed at owner-operators leased to carriers. Its broader commercial lines and workers compensation resources make it relevant for established carriers that want trucking auto coverage alongside other business insurance from one insurer. It is a carrier product, so freight brokers looking for contingent coverage or a BMC-84 bond will need a specialist.
How working with them works
Sentry's trucking insurance is available only through 65 appointed agencies that specialize in trucking. A prospect can fill in a contact form on Sentry's site, and Sentry will match them with a trucking-experienced agent who builds a plan. Buyers can also use the find-an-agent tool or call Sentry directly.
Existing customers can log in, make payments and file claims online. Premiums are not published and are set through underwriting. The telematics discount applies at bind when data is shared through TruckerCloud.
Because Sentry's trucking coverage is only available through appointed agencies, the agent you choose matters. Ask how many trucking accounts the agency places with Sentry and which other insurers it can quote, so you can compare options side by side before you bind.
Questions to ask before you sign
Ask your Sentry agent to confirm every coverage on the proposal, including auto liability limit, physical damage values and deductibles, motor truck cargo limit and deductible, general liability and any non-trucking liability for leased owner-operators.
Request the cargo form and exclusions. Ask about theft conditions, unattended vehicle rules, refrigeration breakdown, restricted commodities and high-value load limits.
Ask whether the policy includes any E&O or cyber coverage, or whether those are separate policies.
Confirm that Sentry will file your federal proof of liability (BMC-91X) and state filings, and how quickly. If you broker freight under separate authority, plan to source a BMC-84 bond and contingent coverage elsewhere.
If you will share telematics data through TruckerCloud, ask what data is shared, how it is used at renewal, and how the discount is applied.
Check Sentry's current AM Best rating yourself on the AM Best site. Ask how claims are assigned, how quickly an adjuster responds to a serious accident, and what safety services are included with your policy.
Company background
Sentry was founded in 1904 and was originally known as Hardware Dealers Mutual Fire Insurance Company of Wisconsin. As a mutual company, its business is built around its policyholders. It has more than 2,000 associates in Stevens Point and about 4,000 more around the country, with nine regional offices.
Sentry's commercial business is organized into units including National Accounts, Direct Writer, Transportation, Regional and Specialty. Its personal lines are sold under The General brand. The company also owns SentryWorld, a golf and hospitality complex in Stevens Point.
Sources
Information compiled from public sources. Last verified November 2026. Confirm details directly with the company.
