Dairyland car insurance, as Dairyland describes it
A high-risk specialist since 1953, with an unusually specific published position on SR-22 filing costs.
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The basics, as Dairyland publishes them
- Owned by
- Sentry Insurance Group
- Founded
- 1953
- How you buy
- Online, phone, or independent agent
- Writes
- Nonstandard and high-risk drivers
What Dairyland publishes about itself
Dairyland is a brand, not a single insurer: its coverage is underwritten by one of eight Sentry Insurance Group companies, and Sentry is a mutual. It writes the drivers standard carriers decline — lapses, violations, DUIs, foreign licenses — and it is unusually specific about SR-22s, stating that it most often files them free as part of the policy and can often send them to the state electronically the same day. If you also looked at The General, note that the two share a parent: Sentry acquired The General at the end of 2024.
What is settled, and what is not
Everything on the left is stated by Dairyland. Everything on the right is a question their published material does not answer — which makes it a question worth asking on the phone.
They state this
It says which drivers it is for
In its own words: do you have a lapse in coverage, a violation on your record, or a foreign license? It describes itself as a nonstandard carrier — its term — for drivers considered high risk because of past offenses, lapses, inconsistent payments or other factors.
SR-22 filings, usually with no filing fee
Dairyland states that most often it files your SR-22 free as part of the policy, that in most states it can send the filing to the state electronically the same day, and that some companies and agencies charge extra fees or surcharges. It also sells SR-22 policies online.
It covers FR-44 too, and explains the difference
It states that in Florida and Virginia you may need an FR-44 instead, that an FR-44 may require liability limits significantly higher than the state minimum, and that by law you cannot cancel an FR-44 policy while it is required.
SR-22 with no car
Asked whether you can get an SR-22 without owning a vehicle, it says yes, through its non-owner policy. It publishes three filing types: operator, owner, and operator/owner.
Low down payments and flexible plans
It states flexible payment plans, low down payments and discounts that may help lower cost, and warns that missing payments can lead to cancellation and an SR-26 filing to the state — which is the part that restarts the problem.
They do not
Where its auto product is actually sold
Dairyland publishes no availability statement. What it publishes is a state-by-state table of which Sentry company underwrites Dairyland-brand coverage in each jurisdiction, covering all 50 states and DC — but that says who underwrites where, not what is sold where. Its own sitemap has auto landing pages for roughly 33 states.
Which company writes your policy
One of eight: Sentry Insurance Company, Dairyland Insurance, Dairyland National, Dairyland County Mutual of Texas, Middlesex, Patriot General, Peak Property and Casualty, or Viking of Wisconsin. Dairyland publishes the table; which line of it applies to you depends on your state.
Prior coverage is not required — and is rewarded
Dairyland publishes no prior-coverage requirement, and names a lapse in coverage as a situation it writes. It does offer a transfer discount for moving an existing policy, which rewards prior coverage rather than requiring it. Worth not confusing the two.
No home, renters, life or health
Dairyland publishes auto, motorcycle and off-road products and nothing else. If you are bundling, it is not the company for the other half.
Discounts Dairyland names
These are the credits Dairyland lists on its own site. Which of them you qualify for, what each is worth, and whether it is already on a policy you hold are all questions for an agent — none of them is published, because none of them is the same for two people.
- Multi-car
- Homeowner
- Transfer
- Advanced quote
- Anti-theft
- Defensive driving
- Payment frequency
Dairyland questions
Does Dairyland charge to file an SR-22?
It says most often it does not. In its own words, at Dairyland it most often files your SR-22 free as part of the policy, and it notes that some companies and agencies might charge additional fees or surcharges. It also states that in most states it can send the filing to the state electronically the same day.
Will Dairyland insure me after a DUI or a lapse?
That is the market it describes itself as serving — drivers with violations, accidents, lapses in coverage, DUIs, or a foreign license. It has been doing it since 1953, when it started selling to drivers who could not get standard coverage. Whether it writes you specifically, and at what price, is underwriting, and no website can answer that.
Is Dairyland the same company as The General?
Not the same company, but the same owner. Both are part of the Sentry Insurance Group — Sentry announced in September 2024 that it would acquire The General from American Family, and describes Dairyland as its own nonstandard auto brand. Sentry itself describes its business as a mutual insurance company.
What is an SR-26 and why does it matter?
It is the form that tells the state your SR-22 policy has ended. Dairyland states that if you no longer need an SR-22, an SR-26 is filed to remove it — and separately warns that making payments on time keeps a policy from being canceled and prevents an SR-26 going to the state. A cancellation for non-payment can restart a license problem you already solved.
Can this site get me a Dairyland quote?
No. InsuranceXR is not an insurance agency and does not quote any company. Dairyland sells through more than one channel, so whether a given agent can quote it depends on their own appointments. The agent who answers can tell you which companies they represent; we cannot promise Dairyland is one of them.
All 18 companies
Alphabetical, which is the only order here — we do not rank them. The one you are reading is marked.
Find out who will actually write you
Whether Dairyland — or anyone else — will write your profile, and at what price, is underwriting. No website can answer it. A licensed agent can, on a call that costs nothing.
Auto insurance line
(888) 883-0806Calling costs nothing and there is no obligation to buy.
Not an insurer. We connect you with licensed agents.
InsuranceXR is an independent referral service. We are not an insurance agency, we are not affiliated with Dairyland or with Sentry Insurance, and neither has reviewed this page. All trademarks are the property of their respective owners. Everything stated here about Dairyland is drawn from dairylandinsurance.com and sentry.com — its about, underwriting companies, auto, SR-22, non-owner, discounts and resource pages, and Sentry’s own announcement of The General acquisition — read on September 15, 2026.
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