Dairyland Auto Insurance


Dairyland Auto Insurance

Company History


Dairyland Insurance Company’s roots trace all the way back to 1916, when the Hardware Dealers Mutual Fire Insurance Company of Wisconsin begin writing car insurance policies for its members.

The company was originally a property and casualty insurance provider to members of the Wisconsin Retail Hardware Association. Thankfully, that lengthy name was abbreviated when they renamed the company to Sentry Insurance, the parent company of Dairyland.

Still in Wisconsin, fast forward to 1953, when Dairyland Mutual Insurance Company was formed. The company was created by Stuart Struck, an enterprising professor at University of Wisconsin-Madison.


Focus on Nonstandard Car Insurance


Auto insurance was Dairyland’s focus from the start, selling to nonstandard drivers, which includes flawed driving histories, no prior coverage, or less experience as a driver.

This is also our realm of expertise at FLINSCO.com (Florida Insurance Company) in Florida, covering drivers with SR22, DUI, bad credit, traffic offenses, and other issues that make it harder to get insured.

In 1966, Sentry Insurance purchases Dairyland. The company expands into 27 states by that time, offering nonstandard auto policies in each location. Independent agents are made part of the Dairyland team in the 1970s.

The company begins to insure motorcycles in 1975, as they rise to popularity in the late 1960s with Easy Rider among numerous other biker films, and Evil Knievel becoming a household name in the 1970s. Insurance companies by default follow trends in order to cover any potential risks, especially with vehicles, property, and people involved.

Staying at home in Wisconsin, Sentry Insurance expands in 1977, building a new headquarters in Stevens Point.


Credited as Strong and Secure


By 1992, Sentry is first acknowledged by A.M. Best with an A+ rating for financial strength. This boost of credibility allows Dairyland members, workers, and investors alike to be assured of the company’s good standing in the insurance industry.

Sentry turns 100 years old as an auto insurer in 2016, the same year that Dairyland celebrates insuring Hell’s Angels et al for half a century. In 2018, Dairyland rebranded, adopting a new logo and presenting a modern face for its established and trusted products.


Dairyland Auto Insurance Policies


Nonstandard drivers should keep Auto Insurance products from Dairyland in mind whenever they need to cover their vehicles. They offer great products for the hard to insure population at affordable rates, and your FLINSCO.com agent can make it easy for you to bind and renew coverage.


SR22/SR 22/SR-22 Insurance


Simply put, an SR-22 certificate proves that you are carrying auto insurance. It is required if you have offenses such as DUI or DWI, reckless driving, an at-fault accident, driving without insurance, or driving with a suspended license.


SR 22 is a minimum auto insurance requirement, if requested by the State. Your insurance carrier will advise Florida’s Department of Highway Safety and Motor Vehicles that they are covering your driving for certain auto insurance-related situations.

Good news for those with SR22 requirements – Dairyland will often file your SR 22 at no cost when you apply for your car insurance plan with them.

Dairyland offers to issue electronic copies of your SR-22 immediately. They submit it to the State within the same day in many instances, and you can buy your coverage with an SR22 online.

Another document proving financial responsibility called an FR44 may be required in Florida, depending on your driving record. FR-44 certificates are similar to SR-22s in that they verify your car insurance coverage, yet the FR44 may require that your liability coverage limits are higher than the state minimum.



Underwriting & Service Information for Dairyland Policies


Billing Dates & Policies

First Installment

The first premium payment must be submitted 30 days after the policy effective date to keep coverage in force.

Please note that if after the due date or NSF is applied, refer to the last invoice issued. The amount showing on the Payment Due field may include the following month’s premium.


Late Payments

A $5 late fee applies if payment is not made by the due date.


Dairyland’s Lienholder Deductible FAQs


Why is Dairyland’s auto “Lienholder Deductible” coverage important to customers? 


A new car purchase is an expensive undertaking for our fixed income customers taking on a car payment. Many lienholders require a low deductible on Comprehensive and Collision coverages, which makes insurance even more costly. With Dairyland, customers can enjoy the significant cost savings associated with a $1,000 deductible while still satisfying the lower deductible required by many lienholders.

How does “Lienholder Deductible” coverage work?

If selected on a policy, this coverage reduces the lienholder’s deductible to $250 on losses paid directly to the lienholder in the event the insured vehicle is repossessed.

How do I select “Lienholder Deductible” coverage for my customers?

Simply select $1,000 deductibles for Comprehensive and Collision. Then, select the Lienholder Deductible for both Comprehensive and Collision coverages at $250. Make sure Lienholder information is collected on the policy.

Submitting Proof of Prior Coverage

Email Documents to: PLPCdocuments@sentry.com



Need reliable, affordable auto insurance today?

Call an agent at 888.307.1907 or bind your own policy online at FLINSCO.com.