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Founded
1904
Monthly Range
$850-2,600/mo
Coverage Types
5
Deductible
$1,000-5,000
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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.
Sentry Insurance is a strong choice for growing fleets that want an insurance partner, not just a policy. Their fleet safety consulting is genuinely valuable — not a marketing gimmick — and the mutual company structure means they're financially incentivized to help you prevent losses rather than just collect premiums. Single-truck operators won't get as much benefit from Sentry's model, but anyone running 5 or more trucks should absolutely get a Sentry quote. The potential for dividend returns and the measurable impact of their safety programs can make Sentry the lowest total-cost option even if their quoted premium isn't the absolute cheapest.
Monthly Premium
$850-2,600/mo
Deductible Range
$1,000-5,000
Sentry's pricing is competitive for mid-size fleets with established safety programs. They weight fleet safety metrics heavily — operations with dash cams, ELDs, formal training programs, and regular safety meetings can qualify for preferred pricing tiers. Single truck operators pay standard market rates. As a mutual company, Sentry may return premium dividends in profitable years, effectively reducing total cost. Payment plans include monthly, quarterly, and annual options.
| 24/7 Claims | |
| In-House Claims | |
| Risk Management | |
| Safety Programs | |
| Online Portal | |
| Mobile App | |
| Flexible Payment | |
| Multi-Truck Discount |
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