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Sentry Insurance For Owner operators

Best For Single Truck Owner Operators

Sentry Insurance Approach:

Our review team was delighted to find out that Sentry provides custom-fit commercial trucking insurance policies, Sentry also offers industry knowledge-based free consultation, and personal service, especially to single truck owner-operators.

Sentry is a small commercial truck insurance company but they offer service through their network of  65 agencies in all 50 US states.

Sentry Coverages Available:

Policies are available to large fleets, single truck owner-operators, and everyone in-between. Sentry is good commercial truck insurance for owner operators.

Sentry currently insures more than 37,000 truckers, offering a range of liability, comprehensive, physical damage, collision, motor truck cargo, and non-trucking liability (personal use) coverage, etc.

Sentry doesn’t outsource their claims handling, they staff their claims adjusters who specialize in trucking risks.

Unique Features:

  • Custom policies for small owner-operators
  • Pan American coverage
  • Best in-person service and consultation for small owner operators and truckers


  • Flexible coverage options
  • Available in all 50 states
  • Specializes in coverage for owner-operators and personal use liability


  • Limited online information
  • No online quotes are available
  • Need to work with a local agent
  • Smaller company

Sentry Insurance Style of Policy Delivery:

Sentry believes in tailor-making commercial trucking insurance consultation, documentation, and buying process for small owner operators and truckers. We found that they will provide you with the exact fit policy according to your needs and requirements as a small trucking business.

Sentry Insurance Claims Handling:

Sentry also has knowledgeable claims staff who gets trucking nuances (and your challenges or needs as a small trucker). Sentry also offers certified directors of safety with spotless industry experience of 15 to 20 years.

This level of specialization and expertise, which helps non-fleet small trucking business owners, makes Sentry a top contender for the best truck insurance for commercial vehicles.

During our testing, we found that claims can easily be filed over the phone, and after filing policy status can be checked online without hassle.

Sentry boasts an A+ AM Best rating and a below-average number of consumer complaints, according to the NAIC.

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