Last updated: October 20, 2026
This Dairyland insurance review covers what public sources verify about Sentry’s non-standard auto brand: who owns it, whether it files SR22, how it’s rated, and where the data conflicts. We didn’t buy a policy or file a claim, so nothing here is first-hand experience.
The short version is that Dairyland’s case is acceptance and a filing fee its own page says is generally waived. Its case isn’t price leadership, because it doesn’t appear in the 2026 cheapest-SR22 lists we checked.
Dairyland Insurance Review: Who Owns It and What It Sells
Dairyland’s about page says Stuart Struck, a University of Wisconsin-Madison professor, formed Dairyland Mutual Insurance Company of Wisconsin in 1953. Sentry Insurance bought it in 1966, when it wrote non-standard auto policies in 27 states. Today it sells auto, motorcycle, ATV and UTV, snowmobile, dirt bike, and scooter coverage.
The underwriter matters when you check ratings. Dairyland’s reviews page names Sentry Insurance Company as the underwriting entity, and AM Best rates the legal entity Dairyland Insurance Company. So always confirm the exact company named on your policy.
One ownership fact changes how you should read comparison guides. Sentry also bought The General from American Family, with a closing on January 1, 2025 according to Sentry’s press release. Dairyland and The General are now sister brands. Our The General review covers the other half of that pair.
Dairyland SR22 Filing, Non-Owner and FR-44
Dairyland’s SR-22 page says the company generally doesn’t charge a fee to file an SR-22. It also says it may file electronically by the following day in states that allow it, after the policy is bought and any required payment is complete. Note the word generally. It’s the company’s wording, not a guarantee for every state.
For drivers without a car, the non-owner page says you may be able to use a non-owner policy to satisfy an SR-22 requirement. It gives no state list and no price. Insurify, a comparison site, says Dairyland offers same-day non-owner filings with low down payments and no producer fee. Treat that as a lead to confirm, not a promise. Our non-owner SR22 guide explains how these policies work.
FR-44 is less clear. Insurance.com and AutoInsurance.com say Dairyland files FR-44 certificates in Florida and Virginia. Dairyland’s own SR-22 page compares the two forms but doesn’t say it files an FR-44. So ask before you rely on it, and read our SR22 vs FR-44 guide first.
Where Dairyland Sells: Sources Disagree
Dairyland’s homepage and about page don’t list states. Third parties give different counts. Insurify (September 28, 2026) says all 50 states and Washington, DC. Insurance.com (May 11, 2026) lists 33 states, and AutoInsurance.com lists 38. NerdWallet says 37 or more, excluding Hawaii and some others.
Those counts can’t all be right. So check your own state on the company quote page or with an agent before you spend time on a quote.
Dairyland Insurance Review: Ratings, Complaints and Reviews
AM Best rates Dairyland Insurance Company A+ (Superior) with a stable outlook, affirmed July 29, 2026, in financial size category XV. That rating speaks to claims-paying ability.
Complaint data is less consistent. Insurance.com (May 11, 2026) reports an NAIC complaint index of 0.92, below the 1.0 baseline. AutoInsurance.com reports about 1.49 times the average complaint volume. Insurify shows 1.49 as a score out of five, which looks like a mislabeled version of that same number. NerdWallet says Dairyland is close to the expected number of complaints. We couldn’t identify the data year behind any of these.
Trustpilot showed 4.4 out of 5 from 10,307 reviews when we checked on September 29, 2026. Seventy-five percent were five-star and eight percent were one-star. Reviewers praise helpful staff, quick quotes, and affordable rates. They complain about delays in getting policy documents, unexpected fees, and higher premiums than quoted. Dairyland holds a paid Trustpilot subscription and replies to about 42% of negative reviews.
NerdWallet rates Dairyland 4.3 stars in its September 1, 2026 high-risk list. J.D. Power doesn’t rate it, since it’s a non-standard carrier. We couldn’t confirm a BBB profile that clearly belongs to the Dairyland underwriter, so we don’t cite one.
What Dairyland Costs: Three Sources, Three Answers
Insurify (September 28, 2026) lists $102 a month for liability-only and $248 for full coverage, without showing its assumptions in the page we read. NerdWallet lists $3,989 a year for full coverage for a 35-year-old, against a $2,344 national average, and $820 for minimum coverage against $644. AutoInsurance.com lists $4,851 for full coverage and $1,946 for minimum. Insurance.com says Dairyland doesn’t provide rates to its data provider.
| Source | Liability-only or minimum | Full coverage | Note |
|---|---|---|---|
| Insurify (September 28, 2026) | $102 a month (liability-only) | $248 a month | Assumptions not shown on the page we read |
| NerdWallet | $820 a year (national average $644) | $3,989 a year for a 35-year-old (national average $2,344) | Minimum coverage compared with the national figure |
| AutoInsurance.com | $1,946 a year | $4,851 a year | Profile not stated |
| Insurance.com | Not provided | Not provided | Dairyland does not provide rates to its data provider |
Annualized, Insurify’s $248 a month comes to $2,976, well below NerdWallet’s $3,989. That gap shows how much profile assumptions matter. These figures use different profiles, so don’t average them. But they point the same way: Dairyland’s prices sit above the national averages the sources quote. That fits its role. It writes drivers that standard carriers avoid. See our cheapest SR22 insurance companies comparison for who wins on price.
Dairyland Insurance Review: Strengths and Open Questions
Verified Strengths
- An A+ (Superior) AM Best rating on the legal entity, affirmed July 29, 2026, backed by a parent that has written non-standard auto since 1966.
- Company wording that it generally doesn’t charge to file an SR-22, and that it files electronically by the next day in states that allow it.
- A 4.4 out of 5 Trustpilot score across more than 10,000 reviews, with praise for staff and quick quotes.
Open Questions
- Prices that sit above the national averages quoted by NerdWallet and AutoInsurance.org.
- An unclear state footprint, since counts run from 33 states to all 50.
- No company statement that it files FR-44, and complaint indexes that disagree on whether it’s above or below average.
- Reviewer complaints about slow policy documents and unexpected fees.
What We Could Not Verify in This Dairyland Insurance Review
Several items stayed unverified after our checks. The company pages give no down payment amount. No dated source gave us a reliable state list. The NAIC data year is missing behind every complaint index we found. And we couldn’t confirm a Dairyland-specific BBB profile.
We also have no data on claims handling from our own testing. If you have filed a claim with Dairyland, your experience is better evidence than anything in this Dairyland insurance review. Use ours as a starting checklist, not a verdict.
Payment Options and Discounts
The company pages we read describe bill pay and app access but give no down payment amount. Insurify says Dairyland offers a discount for paying quarterly, semiannually, or annually. Insurance.com mentions discounts for paid-in-full and automatic payments. These come from comparison sites, so ask for the exact discount and the down payment in writing before you commit.
Who Should Get a Dairyland Quote
- Drivers declined by standard carriers after a DUI, a lapse, or repeated violations. Dairyland’s SR-22 page lists these as reasons for a filing.
- Drivers who need an SR22 in a state where Dairyland sells and files. Confirm the state first.
- Owners of motorcycles, ATVs, or snowmobiles who want one insurer for several vehicles.
- Non-owners who need a filing without a car. Ask for the price and the filing timeline in writing.
Before you buy, ask five questions. First, what’s the down payment? Second, does the filing fee repeat each term? Third, does the company file in my state, and does it file FR-44 if I need one? Finally, which payment methods does it accept? The homepage mentions bill pay and a mobile app but lists no methods.
Our view: get a Dairyland quote as part of a group of five, not as your first call. It’s a fallback for acceptance, and the verified strengths are its A+ financial rating and the no-fee filing language. Compare it against the best high risk auto insurance companies before you commit.
This article contains no affiliate or quote links. If we add any, we will disclose them here. Figures were checked on September 29, 2026 against the sources named above.
The team at High Risk Auto Guide isn’t a licensed insurance agency. The information in this article is educational and based on official, verified sources as of the date noted. Confirm the details that apply to your specific case with your state’s DMV/BMV or with your own insurance company.
