Sentry Insurance (Dairyland, The General) auto insurance

Overview

Sentry Insurance is a mutual insurer based in Stevens Point, Wisconsin, best known in business insurance. Its personal auto premium comes from two consumer brands that specialize in nonstandard auto insurance: Dairyland, sold through independent agents and by phone, and The General, sold directly to consumers. Sentry Insurance Group ranked #16 among U.S. private passenger auto insurers by 2025 direct premiums written according to NAIC market share data, with $3.07 billion in auto premiums and a 0.83% national share. That total includes The General, which Sentry bought at the end of 2024.

Both brands focus on drivers that standard insurers often price highly or turn down: people with violations or a DUI, gaps in coverage, a foreign license, or a state requirement to file an SR-22 or FR-44 certificate. Dairyland also insures motorcycles, ATVs and other off-road vehicles.

History

Sentry traces its roots to 1904 and the founding of Hardware Dealers Mutual Fire Insurance Company of Wisconsin, its original name. Today it employs more than 2,000 people in Stevens Point and about 4,000 elsewhere, and is led by chairman and CEO Pete McPartland. Its commercial units serve manufacturers, contractors, national accounts and, through its Hortica affiliation with Florists' Mutual Insurance Company since 2015, horticulture businesses.

Dairyland has sold coverage since 1953. Dairyland-branded policies are underwritten by Sentry group companies including Dairyland Insurance Company, Dairyland National Insurance Company, Viking Insurance Company of Wisconsin, Patriot General Insurance Company, Peak Property and Casualty Insurance Corporation, Middlesex Insurance Company, Sentry Insurance Company and, in Texas, Dairyland County Mutual Insurance Company of Texas, a county mutual insurance company company.

On September 12, 2024, Sentry agreed to buy The General from American Family Insurance, which had owned it since 2013. The deal closed on December 31, 2024. AM Best put the price at about $1.0 billion in cash and consideration, or $1.7 billion including assumed liabilities and required capital. The General began in 1963 as Permanent General Agency and is based in Nashville, Tennessee. Sentry's corporate site now describes its personal lines department as sold under The General brand, while Dairyland's website continues to quote and service Dairyland policies through agents.

Auto insurance coverage

Dairyland's auto policies offer liability, collision, comprehensive, uninsured/underinsured motorist, personal injury protection and medical payments where available, and 24/7 roadside help for dead batteries, flat tires, breakdowns, running out of gas and lockouts. It also sells non-owner coverage for people who drive but do not own a car, and it files SR-22 and FR-44 certificates with the state when required. Dairyland insures motorcycles, scooters, mopeds, dirt bikes and ATVs, and policies can be bundled across those vehicles.

The General offers nonstandard auto coverage sold online and by phone. In Texas, The General's coverage is underwritten by Dairyland County Mutual Insurance Company of Texas.

Discounts and programs

Dairyland lists multi-car, advanced quote (quoting before your current policy expires), homeowner (even if your home is insured elsewhere), anti-theft and safety features, prior insurance or transfer, payment frequency (paying in full or quarterly) and defensive driver course discounts, plus savings for bundling auto with motorcycle or off-road policies. Availability varies by state.

Dairyland emphasizes flexible payment plans and low down payments, which matter to many nonstandard buyers. Its discount list does not include a telematics or usage-based program.

Claims

Dairyland customers can report claims online through their account, as a guest online, or by phone at 800-334-0090, around the clock. Claim status and claim payments can be viewed online, and the Dairyland app handles payments, account access and ID cards. The General takes new claims 24/7 at 800-280-1466; its team for existing claims works weekdays.

Neither Dairyland nor The General is included in the J.D. Power U.S. Auto Claims Satisfaction Study, which covers the largest insurers.

Ratings and reputation

AM Best rates the Sentry Insurance Group's property/casualty companies A+ (Superior). The General's website cites that rating as current as of June 2025, and AM Best raised The General's three insurance companies to A+ (Superior) in February 2025 after the acquisition, citing Sentry's operational and financial support.

Customer satisfaction scores are middling to low. In the J.D. Power 2026 U.S. Auto Insurance Study, Dairyland scored 630 in the Southwest (tied for 6th of 13, below the 638 average) and 624 in Florida (10th of 14, below the 639 average). The General scored 606 in Florida, 13th of 14.

Who it suits

Sentry's brands suit drivers who need coverage despite a spotty record, an SR-22 or FR-44 requirement, a lapse in coverage or a foreign license, and riders who want motorcycle or off-road coverage from the same company. Shoppers can choose an agent (Dairyland) or buy direct (The General). Drivers with clean records will usually find more discounts and stronger satisfaction scores with standard carriers.

• Strengths: A+ (Superior) financial strength backing nonstandard policies; SR-22, FR-44 and non-owner coverage; motorcycle and off-road expertise; both agent and direct buying options.
• Weaknesses: Below-average J.D. Power satisfaction scores in every region where Dairyland or The General was ranked in 2026; no telematics discount listed; not sold in every state; brand roles are shifting after the 2024 acquisition of The General.

How to contact Sentry Insurance (Dairyland, The General)