Sentry (Dairyland) Insurance Review & Complaints: Commercial Insurance

Sentry Insurance owns Dairyland Insurance and Dairyland Cycle Insurance, and the Sentry Dairyland Insurance family provides life insurance, auto insurance, worker's comp, and commercial property coverage. The Sentry Dairyland Insurance company rating is A+ with the Better Business Bureau.

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Eric Stauffer is a former insurance agent and banker turned consumer advocate. His priority is to help educate individuals and families about the different types of insurance they need, and assist them in finding the best place to get it.

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Written by Eric Stauffer
Founder & Former Insurance Agent Eric Stauffer

Leslie Kasperowicz holds a BA in Social Sciences from the University of Winnipeg. She spent several years as a Farmers Insurance CSR, gaining a solid understanding of insurance products including home, life, auto, and commercial and working directly with insurance customers to understand their needs. She has since used that knowledge in her more than ten years as a writer, largely in the insuranc...

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Reviewed by Leslie Kasperowicz
Farmers CSR for 4 Years Leslie Kasperowicz

UPDATED: Jun 1, 2022

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Dairyland Insurance

Financial Strength

Sentry Insurance is a Wisconsin-based insurer focusing on commercial and small business insurance products. They serve a variety of industries with policies available across the country.

About Sentry Insurance

Sentry’s roots are in the hardware business; the company was created as a mutual insurer to serve the Wisconsin Retail Hardware Association in 1904. The company’s original name, Hardware Mutual Insurance, reflected that focus.

The company expanded over the years to provide coverage to a wide variety of businesses and industries as well as providing coverage across the United States. Today they operate as part of Sentry Insurance Pool, which owns – in addition to a variety of Sentry branded companies – Dairyland Insurance and Dairyland Cycle.

Sentry sells commercial insurance to companies large and small through brokers and agents. Their headquarters is located in Stevens Point, Wisconsin. In 2018, the company ranked at number 694 on the Fortune 1000 list and is one of the biggest commercial insurance companies in the nation.

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Sentry Products

Sentry writes packaged commercial products as well as offering extras like worker’s compensation and employee benefits. They write policies for a lot of industries, specifically trucking, construction, dealerships, manufacturing and processing, retailers and distributors, and the service industry.

Business Owner’s Policy (BOP)

This package policy is generally aimed at smaller to medium-sized businesses and includes all the most common coverages grouped together. Sentry’s BOP includes a combination of these coverages depending on the type of business:

  • Business liability
  • Commercial property coverage
  • Premises and product liability
  • Cyber liability
  • Employee benefits liability
  • Business personal property coverage

Commercial Property

Sentry offers a range of commercial property insurance options that can be selected from to customize your coverage. These products can also be combined with other coverage options, such as liability and commercial auto, to create a complete package.

The commercial property options from Sentry are:

  • Crime insurance
  • Inland marine
  • Business personal property
  • Business income
  • Equipment breakdown
  • Building insurance

Commercial Liability

To add on to the selected commercial property coverage, Sentry has a variety of liability options as well. General liability is usually the main component of this area of business coverage, but Sentry also has some more specific liability policies to choose from based on the company’s needs.

  • Premises and product liability
  • Cyber liability
  • Employment practices liability
  • Personal and advertising injury insurance
  • Employee benefits liability
  • Errors & Omissions coverage for agricultural consultants, contractors, dealers, manufacturers, and printing/graphic art
  • Commercial Umbrella insurance

Business Auto

Sentry has a variety of business auto-related policies to select from. In addition to standard commercial auto policies for leased, owned or rented vehicles used for business purposes, they also offer:

  • Dealership auto coverage
  • Commercial auto liability
  • Motor carrier coverage
  • Physical damage insurance
  • Non-trucking liability

Worker’s Compensation

Sentry offers worker’s compensation insurance as either a stand-alone product or as part of a custom package.

They have options for businesses of all sizes, including for large companies that pick to be self-insured. They also have large and small deductible programs and a guaranteed cost program. Sentry can also work with state worker’s compensation pools.

Life and Retirement

Sentry offers retirement plans as well as life insurance policy options for business owners and employees.

Sentry offers a key person life policy option that is designed to provide a death benefit for the business owner and top employees without which the business would struggle. They also have a personal life policy, offered in both whole life insurance and term life insurance.

In addition to traditional 401(k) plans, Sentry also has a Roth 401(k) and Safe Harbor 401(k). Other retirement planning choices include profit sharing, money purchase, cash balance plans, and a variety of other investment options.


Sentry does not offer rates online, which is standard for the commercial insurance industry. Because business insurance is complex and varies based on the industry, quotes require some in-depth information about the business. This means they are best obtained by speaking directly with an agent or broker.

Sentry is a big company with a lot of policies in force, which indicates they probably have competitive rates.


Sentry Insurance offers many discounts for you to take advantage of, including:

  • Multi-vehicle discount
  • Driving course discount
  • Homeowners discount

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Claims can be reported either online when logged into a customer’s account, or over the phone via a 24/7 toll-free phone number. The status of the claim can then be monitored through the same customer portal.

There are two online customer tools; Sentry Insight is the main customer portal, and Sentry Connect is referred to as a “self-service website”. Both appear to provide many of the same services – claims management and policy information – and it is unclear why there is a need for both options.

Sentry provides an online provider that searches for worker’s compensation claims, both for in-network doctors and other medical professionals as well as for in-network pharmacies. This can be accessed by the employee at any time.

Customer Online Experience

Sentry Insurance’s website makes it easy to compare different insurance policies for businesses and commercial clients. The carrier does not provide much information about their claims process or detail a claim‘s response time frame. Online bill pay is an option, as well as 24/7 claims reporting by phone, fax, or internet, which are great customer service features. So, Sentry is pretty good in terms of user-friendliness

Ratings and Consumer Reviews

Sentry Insurance has an A+ rating by the Better Business Bureau (BBB). The site lists 120 complaints on file in the past three years, which is not high when compared to the size of the company and the number of policies in force. Of the complaints, 43 of the 120 were closed in the past 12 months.

There are a few reviews of the company on the BBB page. Most of them appear to be regarding Sentry Insurance Pool subsidiaries Dairyland Insurance and Sentry Select.

We found a similar situation with the reviews of this company at Pissed Consumer. There are 35 complaints here, most of which refer to car and motorcycle policies. It is unclear whether any of these are for Sentry’s commercial auto policies, but may appear to be issued by subsidiaries writing personal insurance. There are a few complaints about failure to pay worker’s compensation claims.

We were unable to find much that related directly to Sentry’s commercial insurance policies. That is pretty standard with business insurance, as problems are usually handled in other ways and leaving a complaint online is far less common.

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The Bottom Line

Sentry is a huge commercial insurance company and worth a look if you are looking to cover your business of any size. They have a long history, a good variety of products, and their size indicates they are doing something right. As always with commercial insurance, it is worth taking the time to sit down with a trusted agent or broker to help choose the right company and policy for your company. – Sentry may or may not fit the bill.

Since Sentry doesn’t offer an online quote tool, it’s hard for potential customers to compare its prices to other auto insurance providers. Our experts compared premium costs across 10 providers. Sentry was the second most expensive provider in Delaware, South Carolina, and Idaho. If you’re looking to buy cheap insurance, Sentry may not offer the best deal.

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