Boring Insurance Agency
A safety manager in a fleece vest holding an open driver qualification file at a filing cabinet, a drawer of similar folders beside her

Is a group captive a good idea for a trucking fleet?

It can be for a fleet with consistently better-than-average losses, a committed safety culture and the capital to post collateral, because the fleet shares in the underwriting result instead of paying for the class average. It is a poor fit for a fleet with volatile losses, thin cash or a short horizon, since bad years cost more and leaving usually takes time and money. Compare it with a conventional quote over several years, not one.

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Tell us the situation.

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One licensed human replies the same business day — not five agents, not an auto-responder. If the policy you have is already the right one, we will tell you.

We use this to quote and service your insurance, and we do not sell it or pass it to lead networks. Privacy policy.

Large fleets. Lori takes on only a few large fleets at a time, so each one gets a full renewal: the submission built properly and shopped with every insurance company that fits. Two openings remain for the rest of 2026.

Lori Adams, TRS, Commercial Trucking Insurance Advisor
/ Who handles this

Lori Adams, TRS

Commercial Trucking Insurance Advisor

Twenty-five years in trucking insurance. Knows the filings, the radius rules and the carriers that will actually take the risk.

Transportation Risk Specialist (TRS)

/ Don’t want to read all this?

Send us what you have. We’ll tell you if it’s right.

Your current policy paperwork, a renewal notice, or nothing at all. A licensed agent reads it and replies the same business day.

The detail

  • The NAIC describes a captive as, in its simplest form, a wholly owned subsidiary created to provide insurance to its non-insurance parent company or companies, essentially a form of self-insurance in which the insurer is owned by the insured.

    NAIC, Captive Insurance Companies

  • A risk retention group is a liability insurer owned by its members, organized under the federal Liability Risk Retention Act of 1986, and limited to insuring the liability risks of its members.

    Liability Risk Retention Act of 1986, 15 U.S.C. 3901-3906

What this means for you

  • You are buying into a group’s results. Members share losses through the captive’s structure. A strong group improves your result; a weak member hurts everyone until it leaves.
  • Capital comes first. Members usually contribute capital and post collateral on joining. Ask how much, in what form, and when it comes back.
  • The exit is part of the decision. Find out how long open claims keep your collateral tied up after you leave, and what happens to your share of any surplus.
  • Safety requirements are real. Captives commonly require members to meet loss-control standards and attend meetings. A fleet that resents oversight will not enjoy one.
  • Compare over a cycle. A captive can look expensive in year one and cheaper by year five, or the reverse. Model several years against a conventional program before deciding.

Related questions

What is the difference between a captive and a risk retention group?

Both are owned by the businesses they insure. A risk retention group is organized under the federal Liability Risk Retention Act, can write only liability insurance, and once licensed in one state can operate in others under that act. A captive is formed under a state’s captive law and can be structured in several ways, often reinsuring a conventional policy.

How do I know if our fleet is ready for a captive?

Look at three to five years of losses against the premium paid. If losses have been steadily below what you pay, the safety program is written and enforced, and the business could post collateral without straining cash flow, a captive is worth modeling. If losses swing widely from year to year, a conventional program is usually safer.

How hard is it to leave a group captive?

Harder than leaving a conventional policy. Collateral usually stays with the captive until the claims from your years in it close, which can take several years for injury claims, and the terms for returning any surplus vary. Read the exit provisions before joining, and compare a captive with conventional quotes rather than in place of them.

Need this handled?

Reading about it and having it handled are different jobs, and the second one is ours. We place the accounts other brokers decline — claims history, a cancellation, an unusual operation, a business nobody wants to underwrite twice — and we will tell you when the policy you already have is the right one. Tell us the situation and a licensed human replies the same business day.

Lori takes on only a few large fleets at a time, so each one gets a full renewal: the submission built properly and shopped with every insurance company that fits. Two openings remain for the rest of 2026.

Written by the licensed brokers at Boring Insurance. Last updated 2026-10-11. See all guides.

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