Article

Self-Insured Trusts and Captive Insurance

8/26/2025

Single parent captive insurance companies and self-insured trusts are both sophisticated vehicles for businesses eager to transcend traditional insurance models. Yet, the journey of forming and managing each is vastly different, and nowhere is this more evident than when examining the drawbacks faced by self-insured trusts.

Drawbacks of a Self-Insured Trust: A Closer Look

Imagine a company deciding to “go it alone”—setting aside its own funds to cover future claims, rather than paying premiums to a commercial insurer. It sounds empowering, even strategic. However, beneath the surface, significant challenges lurk.

Financial Risk and Unpredictability

Perhaps the greatest challenge lies in financial risk. Once a business opts for a self-insured trust, it shoulders the full weight of any claims that arise. This can be manageable until an unexpected or catastrophic loss hits, potentially threatening the financial stability of the trust and the company itself. Unlike insurance, where the cost is fixed and predictable, self-insured trusts must constantly anticipate—and prepare for—the unknown. Large claims or legal changes can swiftly drain the trust, and if funds prove inadequate, members may face additional assessments to cover shortfalls.

Joint and Several Liability

In trust structures that involve groups—such as group workers’ compensation or benefit plans—joint and several liability becomes a real concern. This means every member of the trust may be responsible for all liabilities incurred by the trust, not just their own. Should another member default or the trust become insolvent, others may be called upon to make up the difference, exposing them to risks beyond their own claims.

Administrative Burden

Handling a self-insured trust is not a passive endeavor. There is a steep administrative burden: overseeing actuarial estimates, managing and adjudicating claims, ensuring regulatory compliance, and maintaining fiduciary standards take considerable expertise, time, and cost. Many businesses underestimate these demands, only to find themselves grappling with complex regulations, audits, and compliance filings year after year.

Regulatory and Compliance Exposure

Self-insured trusts must navigate an intricate web of legal requirements—ERISA, state department of labor rules, and specific trust laws. Compliance failures can result in fines, penalties, or forced closures of trust arrangements. Especially for multi-state operations, these requirements become even more complicated: exposures outside of a given state sometimes cannot be covered by the trust at all.

Unforeseen Losses and Resource Commitment

Even for well-managed trusts, unforeseen losses and resource commitment pose persistent challenges. It is difficult to predict the true extent of future claims. Small misjudgments or an overoptimistic view of risk can leave a trust drastically underfunded. Maintaining an adequate reserve demands discipline, and companies must be vigilant against reallocating funds meant for claims to other business needs—a temptation that risks leaving the trust unable to meet its obligations when disaster strikes.

Example: An Unexpected Financial Hit

Consider a group self-insured workers’ compensation trust. If claims suddenly balloon due to a workplace accident or regulatory change, the trust might lack sufficient reserves and have to assess further charges against its members—even years after the incident. The unpredictable nature of these events means the true cost of participation is never completely certain.

Aspect

Self-Insured Trust

Captive Insurance Company

Pros

   

Cost Savings

Avoid insurance premium taxes and carrier profits.

Retain underwriting profits and excess reserves.

Customization

Flexible benefit plan design.

Highly customizable for multiple lines of risk.

Transparency

Direct access to claims/utilization data.

Deep analytic access for claims and risk management same as self insured trust.

Control

Employer oversees plan and funding.

Increased control over policies, claims, investments.

Speed of Implementation

Often faster and less complex. Less regulation.

Speed to market contingent on utilization of effective independent service providers/consultants. Working with experienced service providers can reduce speed to market drastically.

Regulatory Simplicity

Fewer insurance regulations (but ERISA/fiduciary rules apply).

Can access global markets, tax advantages if properly structured.

Cons

   

Financial Risk

Bears entire risk for claims, potential reserve shortfall.

High initial capital outlay, ongoing regulatory oversight. Cell structures can lessen the initial capital outlay.

Claims Volatility

Unpredictable; catastrophic claims can quickly deplete funds.

Reinsurance and pooling can manage volatility, but still financial exposure.

Joint/Several Liability

Members of group trusts may be liable for defaults of others.

Isolated to insured’s own risks in single parent/cell captive.

Administrative Burden

Management of trust, actuarial, fiduciary compliance is significant.

Requires professional captive management, regulatory compliance. Independent unbiased service providers paramount for success as they act as “back office” to captive insurance company.

Regulation/Fiduciary Risks

Complex ERISA, labor department, and fiduciary standards.

Must meet insurance regulatory standards and audits. Effective captive management needed.

Resource Commitment

Maintaining adequate reserves is a constant challenge.

Ongoing capital management and reserves required.

Customization Limits

Less coverage flexibility for unusual/special risks.

Maximum flexibility across multi-risk lines.

Choosing a captive insurance company over a self-insured trust offers organizations not just risk retention but a powerful platform for strategic insurance management. Captives provide greater security and predictability by operating as formal insurance entities regulated by state insurance departments, allowing for robust protections against catastrophic losses and access to global reinsurance markets. This access ensures businesses can efficiently transfer risk above certain limits, a safety net not typically available with self-insured trusts.

Captives also enable tailored coverage for specialized or emerging risks that may be excluded from traditional commercial policies or self-insured trust arrangements. Owners gain comprehensive control over their insurance programs—designing policy terms, claims management, and investment strategies—leading to more effective risk mitigation and potentially improved organizational safety and outcomes.

Financially, captives offer distinct advantages. Premiums paid are deductible (assuming regulatory requirements are met), and underwriting profits remain with the organization, unlocking additional long-term savings and investment potential. This structure often provides more stable costs than self-insured trusts, which are vulnerable to unexpected claims that could rapidly deplete reserves.

Finally, the governance, transparency, and reporting standards inherent in a captive insurance company foster confidence with regulators, stakeholders, and reinsurers. For organizations seeking truly customized risk financing, enhanced control, and the ability to weather unexpected events, a captive delivers benefits that extend well beyond the capabilities of a self-insured trust. For a deeper dive into Single Parent Captives, read the article here. 

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