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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...

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UPDATED: Sep 15, 2020

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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 for 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 package 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 customized 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 choose 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 choose to be self-insured. They also have large and small deductible programs and a guaranteed cost program. Sentry can also work with state workers 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 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.

Rates

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.

Claims

Claims can be reported either online when logged into a customer 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 search 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.

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Ratings and Consumer Reviews

Sentry Insurance has an A+ rating with 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 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 in regards to 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 relates 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.

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.

For a list of companies that we recommend, visit our Best Insurance Companies page.

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Review Information

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Sentry Insurance
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About Eric Stauffer

Author: Eric StaufferI am a former insurance agent and banker turned consumer advocate. My 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.

17 Comments

  1. I was hit by a SENTRY customer and my car was totaled 4 months.

    Nothing resolved, and they won’t pay to rent a car total either.

    My suggestion is to get an attorney to start with because you’ll need it…

    Reply
  2. Sentry is also carried by Harley Davidson Insurance. A guy hit me on another motorcycle was given a ticket, but come to find out he had Dairyland some insurance company. He was guilty and they refused to accept liability and put the claim on my insurance and my record. Nothing but crooked dealings here there is no one to stop them, I guess the insurance commissioner must be on their payroll. Unscrupulous and unethical cheats, the only way to hurt them is to tell everyone you can to not buy insurance from them. Always look at the fine print to see if they are actually behind the insurance company you are buying from.

    Reply
  3. I opened a policy for 2 hours for a vehicle I was supposed to be purchasing. The vehicle ended up being junk and I declined the purchase. I called to cancel the policy and they told me I needed to submit proof that I did not possess the vehicle. Then they had to “review” my cancellation request. 3 days later I was told it was accepted and IF I was due a refund I would receive a check within 5-15 days. Did not happen. Then I received a letter stating it could take up to 30 days…for having a policy for 2 hours?? Still, I waited. Nothing. I finally called back and received a PARTIAL refund. They stole $60 from me. Shortly after, I got a bill in the mail for $5.27. Because while they were “reviewing” my cancellation request, they were charging me for a vehicle I didn’t have. So I called back again and was told my policy would be backdated to the date I canceled and the $60 would be refunded. I have wasted countless hours calling and babysitting these people. Today I called back to confirm my refund would be sent and was told it had been denied and those were processing and cancellation fees and that I was lucky to get a refund at all. These people are crooks and I am going to report them to the Better Business Bureau. $65 for holding a policy for 2 hours for a vehicle I never owned. Disgusting, unethical, and should be illegal.

    Reply
  4. This Company Sentry Ins, is the worst company on the planet. Do not use them for any insurance needs and don’t give them a penny. I used them for auto insurance years ago and they screwed me on a claim. They even hired lawyers and investigators but denied my claim. It seems like they would much rather give the money that they should use to pay customers for claims to the lawyers and investigators than to the customers.

    Reply
  5. ABSOLUTELY THE “WORST” COMPANY OUT THERE!! DAIRYLAND INSURANCE COMPANY! DO NOT USE THEM FOR ANYTHING. IF SENTRY INSURANCE COMPANY WANTS TO CONTINUE TO BE A COMPANY WITH PRIDE, THEY NEED TO CHECK INTO THE WAY DAIRYLAND IS TREATING THEIR CUSTOMERS…. MAYBE DROP THEM FROM SENTRY ALL TOGETHER! THEY HAD SOMEONE CALL AND INDICATE THAT HE WAS AN EX-POLICE OFFICER, TWISTED AND TURNED EVERY SENTENCE, EVERY LINE, AND THEN SPOKE AS IF THERE WAS INSURANCE FRAUD BEING COMMITTED. WTH IS WRONG WITH THIS COMPANY…. THE INSURANCE WAS PAID MONTHLY, AND THEN WHEN AN ACCIDENT OCCURRED THEY PULLED PAST INFORMATION FROM YEARS AGO INSTEAD OF FOCUSING ON THE CURRENT SITUATION. WHAT GIVES THEM THIS RIGHT!!! IS THERE ANY PRIVACY POLICY EVEN THOUGH NOTHING BAD WAS ON THE RECORD!! EVERYONE SHOULD TURN THIS COMPANY INTO THE INSURANCE COMMISSION… FILE WITH A LAWYER AND SHUT THEM DOWN. THE ADJUSTERS NAME IS “[Redacted]” AND THE SO-CALLED EX-POLICE OFFICERS NAME WAS [Redacted]…. NO LAST NAME. IF THIS CLAIM IS DENIED, POSSIBLY EVEN IF IT ISN’T, I WILL BE FILING WITH THE INSURANCE COMMISSION. HORRIBLE HORRIBLE COMPANY!!!

    Reply
  6. Ive never dealt with a situation were I had a rude adjuster and his supervisor was rude also. They were to busy overtalking you to care to listen to your problem. Maybe have a little more sympathy for people who have been in accidents. I wouldn’t recommend this company to ANYONE. Switching very soon!

    Reply
  7. This company is pure fraud!! I wouldn’t recommend this insurance company to anyone. I literally had coverage with this company for 6 days and paid $381 to start the policy. I canceled the 6th day, due to going with a much cheaper company. I had to send an email stating that I wanted to cancel the policy. Cool. Called today to check the status of the cancellation and the representative stated it was canceled on 05/03/17. Perfect. Then I ask how much of a refund I will be getting back and she proceeds to tell me I am only getting back $61. Are you serious?? She said they keep a portion of it because it was a short rate cancelation and to pay for internal processing. I have never heard of such a thing in my life! I spoke to a supervisor, whose name was [Redacted], who was rude and didn’t know anymore than the untrained representative I spoke with. Asked to speak with his manager, [Redacted], who apparently is in meetings all day and is leaving early so probably wouldn’t have time to call me back today. Needless to say, this company is stealing everyone’s money and should be shut down for fraudulent activity. I will be reporting them to the BBB. Very very very dissatisfied!!

    Reply
  8. Wow! Very disappointed in co feedbacks did I make a big mistake?

    Reply
  9. [Redacted] is the rudest [redacted] ever. Every time i talk to her on the phone she is rude to me like she has a personal vendetta with me. Her tone in her voice changes like she trying to be intimidating. So unprofessional. I will call corporate and complain to every association i see fit until they make some changes. I just paid 350 to be treated like dirt. Im so upset. I dont recommend dairyland auto to ANYONE. Period. Rude n unprofessional. They dont care about their customers.

    Reply
  10. Wow I am shocked at how Dairyland auto Insurance has treated me!! The customer service assoc. are very rude and not helpful at all. Bein as I am also a customer service assoc. I treat my clients with kindness and respect no matter what kind of mood their in. I purchased a non owner policy on March 3rd and cancelled on March 4th. I was told to email my information and it would take 2 to three days to process. I called for the next few weeks and was told they are behind and once it’s processed they would hold my refund check for 7 days then it will be mailed. Well that was apparently a straight up lie. I spoke to a supervisor today March 18th and it’s the first I heard I was not gonna get a refund because they expected me to stay with them for a year ARE YOU KIDDING ME!!!! Elephant insurance was the one that hooked me up with this company so I called them and they were no help either. I will be posting everywhere I can think of to avoid Dairyland Auto Insurance!!!!!!

    Reply
    • I literally am dealing with their corporate office now because I only had them for a week and now they’re telling me I’m only getting back $60 out of the $381 that I paid because they keep a portion of it for internal processing. [Redacted].

      Reply
  11. Do not go with Dairyland Insurance they are Crooks we cancelled our insurance policy we decided to change insurance we had made a payment and decided to cancel the payment they kept half of our payment and wouldn’t return it these people are Crooks they steal from people and their insurance is awful I don’t recommend going with Dairyland Insurance!! There customer service is awful they’re rude and very unprofessional.

    Reply
  12. BEWARE of this company. One of their insured drivers hit my wife head-on. At first they denied coverage. after I proved they were liable they low-balled the value of her vehicle. Then cancelled the rental vehicle before they even cut the check to pay for the vehicle they totaled out. What kind of treatment will they give you?

    Reply
    • We are dealing with them now and have found nothing but rudeness. They claim they are waiting for their client (the person at fault in our accident) to call them back. THEN they will determine liability. Seriously? The person who hit us was cited and we have a police report. I am annoyed that it looks like I will have to file with my own insurance company and let them handle the rest through subrogation. For everyone who has had issues with this company, you need to file a complaint with the insurance commissioner of your respective states. It is clear this company needs to be stopped from doing business.

      Reply
      • This scares me to read this as I was hit last night by one of their insured drivers, who was drunk driving, and I called them this morning to file the claim. I hadn’t heard anything back so I called the claims person to see what is going on and I was basically told that she’ll get to it when she can. They process 100’s of claims and she does them in the order they’re received. I told her that I need a rental and her suggestion was to get it myself and submit for reimbursement. I don’t think I’ll be doing that! I just got my car in March and I’m pretty sure it’s going to be totaled. I think I’ll go through my own insurance after reading these terrible reviews.

        Reply
  13. Was with this company for 28 years on payback car insurance and household insurance and after paying my yearly premium in aug 2013 got letter in jan that i would be cancelled in sept 2014 as no longer having insurance. 28 years of payback and this is how they treat you. Also my household insurance doubled in the last 2 years from 750 to 1495. When called to ask they said that it was due to having tornadoes even though i had never made a claim in 28 years. Nice people Beware.

    Reply
  14. Hey, Eric

    Want to advocate for the consumer? Check out Sentry’s current plan to terminate coverages in Minnesota, especially their auto insurance program. Folks like us who have been with Sentry for years are now being told that Sentry will no longer be writing auto insurance in Minnesota and that their Payback program will end. Additionally, the last 4 years of Payback premiums paid to Sentry will be forfeited. How nice. Unilaterally end a program and then keep the cash!!! Unbelievable.

    Reply

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