We use cookies to give users the best content and online experience. By clicking “Accept All Cookies”, you agree to allow us to use all cookies. Visit our Privacy Policy to learn more.

Manage Cookies
Resources for Businesses My BBB
Share
Business Profile

Insurance Services Office

Sentry Insurance Company

Headquarters

This business is NOT BBB Accredited.

Find BBB Accredited Businesses in Insurance Services Office.

Reviews

This profile includes reviews for Sentry Insurance Company's headquarters and its corporate-owned locations. To view all corporate locations, see

Find a Location

Sentry Insurance Company has 37 locations, listed below.

*This company may be headquartered in or have additional locations in another country. Please click on the country abbreviation in the search box below to change to a different country location.

    Please enter a valid location.

    Customer Review Ratings

    1.06

    Average of 64 Customer Reviews

    Want to share your experience?

    Leave a Review

    Review Details

    • Amy D

      Date: 05/05/2025

      OMG Dairyland...complete CLOWN ACT!!! I was backed into, so I called the police. The gal that hit me was driving her parents 1997 pickup. When the police asked what happened she stated she backed into me and I agreed to that. File a claim thru my ins and Dairyland. Took almost 3 weeks to get an answer. I provided pictures to them as they requested. Couple days later I get and email stating the damage is $1108 and that they issued me a check for $650. Then I look closer at the email and it says claim status closed and $650 is the settlement amount. I was talking with my ins ***** **** this whole time. I took my car to **** body shop to get and estimate and make an appt to get my car repaired. The gentleman at **** said the cost for labor and parts is approx $4000. So basically in their heads they settled with me and closed the case. So I get $650 towards the $4000 it's gonna cost. I get ahold of ***** **** and they said don't cash the check because that means I'm settling for that amount. So now I get to pay a $1000 deductible and ***** **** gets to pay the bill plus I need a rental car for 6 on top of this $4000. Come to find out ***** **** has their own attorneys and they will be taking Dairyland ins to court, so we both can get our money back. Plus the accident is 100% her fault. I can't believe they try and get by with this ****!!! I drive a nice BMW SUV and she was driving a 1997 F150. They could give two ***** about me and my nice vehicle. Big THANKS to ***** **** for taking care of me and this crazy company!! Have fun in court you *********!! Everyone be careful. They are huge crooks!!

    • Trent A

      Date: 04/09/2025

      I had an awful experience dealing this Insurance Company and, in particular, claims representative Ariel ********. From the start, Ariel was extremely rude, dismissive, and unprofessional in every interaction. The accident wasn’t my fault, yet the company has been fighting me every step of the way for months. Instead of resolving the matter promptly and fairly, they seemed more interested in denying responsibility and causing unnecessary delays. The lack of communication, combined with Ariel's unpleasant demeanor, made the situation even more stressful. Ultimately, I had no choice but to hire a lawyer to get the matter resolved. This has been a draining and frustrating process, and I wouldn't wish this experience on anyone. Avoid this company at all costs if you’re looking for fair treatment and decent customer service.

    • Gabrail M

      Date: 04/01/2025

      If I could give them 0 stars, I would. Been paying coverage for 2 years and after needing to file a claim, theyre doing everything in their power not to cover it. The worst company weve ever dealt with. They should be shut down.

    • Mary L

      Date: 02/24/2025

      The worst insurance company ive ever dealt with! I was with Dairyland for several renewals. This company took out extra payment just before the holidays, without my Authorization. That was over $968. In one month. I had to STOP AUTO PAY.. And all they said was its due to a glitch in the system. I had to wait multiple days for a reversal of my money..They have no compassion or respect for the people that this screwed over.. And now that I went with a BETTER Company with Same coverage and over $229.00 a month cheaper..and ask when I cancelled my policy..And they can’t cancel the day you want/ call in.. it’s on the next business day, so they and charger for that day as well.. Each person you talk to you you get a different response or a explanation of why they do things the way they do.. They’re not even accredited with the BBB YOU ************** DAILYLAND

    • Jim F

      Date: 01/14/2025

      Terrible company that should get 2 minus stars but not possible. Sentry/Dairyland Claims Representative **- (whatever that is) outright lied to me when I was making my claim. I was hit by one of their insurees who was 100% at fault, provided a Sentry Insurance card and was ticketed by police! Two weeks since the accident and Claims Rep ** keeps telling me they are investigating. What is there to investigate!! The person was insured as per the insurance card provided at the time of the accident or they were not. If they were not, Sentry/Dairyland should have instantly denied my claim as well as being able AND WILLING to provided a documented paper trail to prove the insurance was not enforce (had lapsed due to non-payment or was cancelled) at the time of the accident. It is my understanding that the client base for Sentry/Dairyland is mostly hard to insure drivers due to multiple accidents and/or tickets. Many clients cannot get insurance through any other reputable and BBB rated/accredited company. If you are considering them, read all these reviews and stay away!

    • Jose D

      Date: 01/10/2025

      Pay all this money for extended full coverage comp and collision and when accident happens they drop me and won't pay for a accident I did some research online and looks like on there reviews I'm not the only one having this issue north carolina requirements is to have insurance i did but don't see why have insurance if you can't use it I also asked then to add my daughters mother they never did

    • David L

      Date: 10/09/2024

      I've dealt with a few insurance companies when the other driver was at fault. While most of them, understandably, worked for their own insured, found a way to to help reaching a timely resolution. My car was side clipped while waiting at the RED LIGHT by one of their insured motorcylist that was lane splitting impatiently. I filed a claim with these guys about a month ago and their only response is that they cannot get ahold of the driver. So i m forced to wait indefinitely despite the obvious circumstance with the photo proofs. Their claim adjust never ever answers the phone or text messages. One of the absolute worst Auto Insurance company I have experienced in my last 25 years of driving.

    • Billy D

      Date: 09/16/2024

      I have been attempting to contact Dairyland Auto Insurance and the first time I managed to get in a call with them I was put through an infinite string of surveys trying to convince me to purchase items. I tried 2 more times after and now I'm being told that the number I am attempting to dial is not available in my area? Their auto insurance is a literal scam. *****.

    • TETIANA K

      Date: 09/06/2024

      It as an amazing company. They paid my $15000 claim fast and with no problem.

    • Amy M

      Date: 08/28/2024

      I have had insurance with Dairyland for about a year now and then my husband gets in a car accident on August *************************************************************************************************************************** that I do not have full coverage on my vehicle when it is financed through a bank when I set up the policy, I made sure I put full coverage on it, but then all of a sudden after I submitted the claim, it shows on the app and on there and that I do not have full coverage that is very suspicious Do not recommend Dairyland to anyone for car insurance. First insurance company I have ever dealt with.

    Sentry Insurance Company is NOT a BBB Accredited Business.

    To become accredited, a business must agree to BBB Standards for Trust and pass BBB's vetting process.

    Why choose a BBB Accredited Business?

    BBB Business Profiles may not be reproduced for sales or promotional purposes.

    BBB Business Profiles are provided solely to assist you in exercising your own best judgment. BBB asks third parties who publish complaints, reviews and/or responses on this website to affirm that the information provided is accurate. However, BBB does not verify the accuracy of information provided by third parties, and does not guarantee the accuracy of any information in Business Profiles.

    When considering complaint information, please take into account the company's size and volume of transactions, and understand that the nature of complaints and a firm's responses to them are often more important than the number of complaints.

    BBB Business Profiles generally cover a three-year reporting period. BBB Business Profiles are subject to change at any time. If you choose to do business with this business, please let the business know that you contacted BBB for a BBB Business Profile.

    As a matter of policy, BBB does not endorse any product, service or business. Businesses are under no obligation to seek BBB accreditation, and some businesses are not accredited because they have not sought BBB accreditation. BBB charges a fee for BBB Accreditation. This fee supports BBB's efforts to fulfill its mission of advancing marketplace trust.