What the Supreme Court’s Montgomery Decision Means for Logistics Companies

The logistics and transportation industry continues to operate under growing legal and regulatory pressure. Rising litigation costs, nuclear verdicts, and stricter compliance expectations have already reshaped the risk landscape for trucking companies, freight brokers, warehouse operators, and third-party logistics (3PL) providers.

Now, the Supreme Court’s Montgomery decision is creating new concerns around liability exposure and operational accountability.

While courts and legal experts continue to interpret the full impact of the ruling, logistics companies should take this opportunity to review their contracts, compliance procedures, and insurance programs to help reduce future exposure.

Businesses seeking transportation-focused risk guidance can explore solutions through Tooher-Ferraris Insurance Group.

Why the Montgomery Decision Matters

The Montgomery decision may influence how courts evaluate responsibility within transportation operations, particularly when multiple parties are involved in the movement of goods.

For logistics companies, this could affect areas such as:

Negligent hiring claims
Driver oversight responsibilities
Independent contractor relationships
Freight broker liability
Vendor management practices
Contractual risk transfer agreements

Plaintiffs’ attorneys may increasingly attempt to hold logistics organizations accountable for the actions of subcontractors, owner-operators, or third-party vendors, even when those parties are not direct employees.

Independent Contractor Relationships Under Scrutiny

Many transportation companies rely heavily on owner-operators and independent contractors. The Montgomery decision reinforces the importance of carefully structuring and documenting those relationships.

Companies should review:

Independent contractor agreements
Dispatch procedures
Safety enforcement practices
Branding requirements
Operational control standards
Compliance documentation

Transportation providers should also maintain strong compliance with regulations established by the Federal Motor Carrier Safety Administration (FMCSA), including driver qualification, hours-of-service requirements, and safety monitoring.

If operational control over contractors becomes too extensive, companies could face arguments that those contractors functioned more like employees, potentially increasing liability exposure.

Contracts and Documentation Are Essential

Strong contracts remain one of the best defenses against transportation-related litigation. Logistics companies should regularly review agreements with carriers, brokers, staffing firms, vendors, and shippers.

Critical areas include:

Indemnification language
Additional insured requirements
Auto and umbrella liability standards
Cargo insurance obligations
Waivers of subrogation
Claims reporting requirements

Documentation is equally important. In the event of a claim, transportation companies may need to demonstrate:

Driver qualification reviews
Safety training records
Vehicle maintenance logs
Drug and alcohol testing compliance
Incident response procedures
FMCSA compliance records

Additional transportation safety resources can be found through the U.S. Department of Transportation.

Insurance Implications for Logistics Companies

The transportation insurance market has already experienced significant challenges due to increasing claim severity and rising jury awards. Decisions that potentially expand liability concerns could place additional pressure on:

Commercial auto insurance pricing
Excess liability availability
Umbrella coverage limits
Underwriting scrutiny

Insurance carriers are likely to continue focusing heavily on safety controls, operational procedures, and claims history during renewals.

Companies with transportation exposures may benefit from reviewing their existing commercial insurance and fleet risk strategies with specialists who understand the industry’s evolving legal environment.

Final Thoughts

The Supreme Court’s Montgomery decision serves as another reminder that logistics companies must remain proactive when it comes to risk management, compliance, and operational oversight.

Organizations that strengthen contracts, improve documentation, enhance safety procedures, and regularly review insurance programs will likely be in a stronger position to manage future legal and financial risks.

At Tooher-Ferraris Insurance Group, we work with transportation and logistics companies to help identify emerging exposures, strengthen insurance strategies, and support long-term operational resilience.

Business Insurance

May 23, 2026

Your General Liability Policy Just Got a New Exclusion — Did Anyone Tell You?

Here is a question worth asking before your next renewal: Does your general liability policy still cover damages caused by artificial intelligence? For many businesses, the answer is no, and most of them have no idea.

In early 2026, major carriers, including Chubb, Travelers, and Berkshire Hathaway, received state regulatory approval to add explicit AI exclusions to general liability, directors and officers, and errors and omissions policies. According to PYMNTS’ reporting, state regulators approved more than 80 percent of those requests. In several states, the exclusions began taking effect as early as January 2026.

This is not a footnote change. It is a structural shift in what standard commercial policies cover — and it is happening right now, mid-policy-cycle, with little fanfare directed at the business owners most affected.

What the AI Exclusions Actually Cover

The new exclusions are broad. They target bodily injury, property damage, and personal and advertising injury tied to generative AI outputs. That includes defamatory content produced by an AI tool, intellectual property infringement from AI-generated materials, and physical damages traceable to AI-driven errors or recommendations.

What does that look like in practice? Consider a marketing firm using an AI content tool that produces a defamatory statement about a competitor. Or a logistics company whose AI-powered routing system makes a recommendation that contributes to a vehicle accident. Or a professional services firm whose AI-assisted report contains a material error that causes financial harm to a client. Under the new exclusionary language, standard GL and E&O policies may not respond to any of those claims.

The Insurance Services Office, the private body that sets industry standards, introduced two new optional AI endorsements that carriers have been moving quickly to adopt. Some carriers, including Berkley, have implemented absolute AI exclusions across multiple lines simultaneously.

Why This Is Catching Most Businesses Off Guard

The problem is not that businesses are ignoring AI risk. It is that most assume existing policies cover it. AI tools have proliferated across operations, marketing, customer service, hiring, and financial analysis — often faster than legal or risk management teams can track. According to research cited by governance analytics firm Techne AI, 88 percent of organizations are now deploying AI in some form, yet fewer than 25 percent have board-level AI governance policies in place.

That gap between deployment and governance is exactly where insurers are drawing the line. Carriers are not saying AI is uninsurable. They are saying they do not yet know what it costs. Until actuarial models catch up, they are moving the risk off their books and onto yours.

The pattern mirrors what happened with cyber insurance a decade ago. A wave of attacks generated claims. Businesses argued their GL policies covered the losses because cyber was not explicitly excluded. Insurers responded by carving cyber out of standard coverage and building standalone products. That market matured into a $12 billion industry. The AI liability market is beginning the same process — just faster.

What to Do Before Your Next Renewal

The first step is a policy audit. Review your current GL, D&O, E&O, and professional liability policies for any new endorsements or exclusionary language related to artificial intelligence. If your policy renewed after October 2025, there is a meaningful chance this language was added without an explicit conversation.

Second, map where AI is actually being used in your business. Recruiting and screening tools, customer-facing chatbots, financial modeling software, and content generation platforms all carry potential liability. Bias in AI hiring tools alone can trigger Employment Practices Liability claims that your EPLI policy may or may not cover depending on how AI is addressed in the language.

Third, ask your broker specifically about standalone AI liability coverage. Specialized products now exist from carriers including Munich Re, with limits ranging from $2 million to $50 million. Premiums vary widely depending on industry, AI use intensity, and governance controls. Businesses that can document structured AI oversight and bias testing tend to achieve more favorable terms.

The team at Tooher-Ferraris works with businesses across industries to identify coverage gaps before they become claims. Start with a review of your commercial insurance program and ask specifically about AI-related exclusions in your current policies. You can also explore specialty programs designed for emerging and non-standard risks.

For more on how AI governance intersects with D&O and E&O exposure, the Risk and Insurance Management Society publishes current guidance at RIMS.org.

Ready to find out what your current policies actually cover in 2026? The team at Tooher-Ferraris has been helping businesses protect what they’ve built since 1932. Contact us today at https://toofer.com/contact-us/ to schedule a no-obligation consultation.

Employee Benefits

May 18, 2026

Small Business, Big Tech: How AI Benefits Tools Are Finally Built for Employers Like You

Picture this: it’s open enrollment season. Your HR manager — who is also your office manager, your compliance point person, and the person who orders coffee – is fielding the same 47 employee questions she answered last year. Meanwhile, three employees chose the wrong plan because they didn’t understand how the deductible worked. Two more never enrolled at all.

This used to be the price of being a small or mid-size employer. You didn’t have a benefits technology budget. You worked with what the carrier gave you: a PDF, a 1-800 number, and a prayer.

That’s changing fast and in 2026, it’s changing in ways that actually matter for employers with 25 to 500 employees.

What AI Benefits Tools Actually Do

Let’s be specific, because “AI” gets attached to every product description regardless of what the technology actually does. In benefits administration, the tools earning the label fall into a few practical categories.

Decision support at enrollment

AI-driven recommendation engines analyze an employee’s life stage, dependent status, and historical plan utilization to guide them toward better plan choices during open enrollment. Platforms like Bswift’s Emma and Employee Navigator’s decision support tools now serve mid-market clients — not just enterprise — and have demonstrated meaningful improvements in plan selection accuracy. According to Clarity Benefit Solutions, AI enrollment guidance can increase HSA contribution rates by 15-25% through better education during the enrollment process alone.

Year-round benefits Q&A

Instead of employees calling HR to ask whether their dentist is in-network or whether they can add a dependent after a qualifying life event, AI chatbots handle these queries in real time, around the clock. The Hartford’s 2026 Future of Benefits Study found that 95% of employers said they want digital tools for routine, transactional tasks — freeing HR staff for the complex issues that actually need human judgment.

Compliance monitoring and eligibility validation. AI systems can flag eligibility anomalies, track ACA reporting deadlines, and monitor regulatory changes across jurisdictions before they become audit findings. For a small HR team without a dedicated compliance specialist, this is where the ROI is most immediate.

What’s Actually Affordable Now

The pricing shift is real. Platforms like Gusto, BambooHR, and Employee Navigator all offer AI-assisted benefits administration at per-employee-per-month pricing that puts the technology within reach of employers who couldn’t consider it two years ago. SHRM’s 2026 State of AI in HR report found that AI in HR is now present in 21% of organizations in the HR technology practice area — and growing. The same report found that 87% of CHROs expect greater AI adoption within HR processes in 2026, up from 83% in 2025.

The pattern from The Hartford’s research is telling: 54% of employers say HR technology and benefits platforms are “highly influential” in selecting benefits carriers and vendors. The technology has moved from back-office tool to strategic differentiator.

What to Ask Before You Buy

Not all AI benefits tools are created equal. Before evaluating any platform, get clear on three questions:

Does it integrate with your payroll system? A benefits platform that doesn’t talk to your payroll creates more manual work than it saves. Ask for a specific list of HRIS and payroll integrations before any demo.
Who owns the data, and how is it protected? Employee health and benefits data is sensitive. Understand where your data is stored, whether the vendor uses it for model training, and what happens to it when your contract ends.
Where does the human support kick in? The best implementations combine digital self-service for routine tasks with experienced specialists for complex claims, disability leave, or sensitive situations. A chatbot that handles open enrollment questions well is a feature. A chatbot that handles a difficult disability claim poorly is a liability.

Your HR technology consulting and HCM consulting teams are the right starting point for navigating the vendor landscape — especially if you’re evaluating platforms alongside a benefits renewal. The technology decision and the benefits strategy decision don’t happen in isolation anymore.

An HR team of two can now administer benefits like a team of twenty. The tools are here. The question is whether you’re using them.

Ready to explore what AI-powered benefits administration looks like for your organization? The team at Tooher-Ferraris has been helping businesses work smarter since 1932. Contact us today to schedule a no-obligation consultation.

Business Insurance

May 12, 2026

Your Business Goes Dark for Three Days — and Your Insurance Won’t Pay. Here’s Why.

Picture this. It is a Tuesday morning and your business cannot operate. Not because of a fire. Not because of a flood. Your primary SaaS platform — the one your entire billing and order management system runs on — is down. The vendor says it could be 48 to 72 hours. Your team is sitting idle. Revenue has stopped.

You call your broker expecting the business interruption claim to be straightforward. It is not. Your standard BI policy has a trigger most business owners never ask about: physical damage to property. No damage occurred. The coverage does not respond.

This is not a hypothetical edge case. It is one of the most significant and least-discussed coverage gaps in commercial insurance today, and it is becoming more relevant every year as businesses build their operations on top of third-party platforms, cloud services, and AI-powered tools they do not own or control.

Why Standard BI Policies Were Never Built for This

Business interruption insurance was designed in an era when the primary threat to operations was physical. A warehouse fire. A burst pipe. A hurricane that takes out a roof. The policy logic made sense: prove physical damage to insured property, document the lost income during restoration, collect the claim.

That model has a fundamental mismatch with how businesses actually operate in 2026. According to the Insurance Information Institute, supply chain and business interruption risk ranked as the second-highest concern among businesses globally — and a growing share of those interruptions have no physical damage component whatsoever. Cloud provider outages, ransomware that triggers a vendor shutdown, SaaS platform failures, and AI system crashes are now among the most common causes of operational downtime — none of which trigger a standard BI policy.

The problem is not new. When a single container ship blocked the Suez Canal in 2021 and disrupted global supply chains for weeks, thousands of businesses discovered that their contingent business interruption policies did not respond to cargo delays without physical damage. The ensuing litigation forced the industry to clarify what it would and would not cover — but for most SMBs, the lesson did not translate into a policy review.

The Products That Fill the Gap — and Who Needs Them

Two coverage types address non-physical business interruption risk, and most small and mid-sized businesses have neither.

Contingent business interruption (CBI) coverage extends BI protection to losses caused by disruptions at a supplier, vendor, or key customer — even without physical damage at the policyholder’s location. For businesses with concentrated vendor dependencies, CBI is not optional risk management. It is core program design.

Technology errors and omissions (Tech E&O) coverage, often paired with a cyber liability policy, addresses operational losses caused by software failures, cloud outages, and technology service interruptions. As businesses embed more AI and SaaS tools into daily operations, the line between a cyber event and a technology failure is increasingly blurry — and the coverage that responds is increasingly specific.

Swiss Re Institute has flagged non-physical business interruption as one of the fastest-growing accumulation risks in commercial insurance, noting that AI and cloud outages can propagate through supply chains in ways that create correlated losses across industries simultaneously. That systemic exposure is exactly why carriers are paying close attention to how these risks are structured — and why businesses cannot assume standard coverage fills the gap.

The Question to Ask Your Broker Today

The conversation is simple: what triggers my business interruption coverage, and what does not? Walk through the three or four operational scenarios that would cause the most serious disruption to your business — a key vendor going down, a cloud platform outage, a software failure during peak season — and ask explicitly whether each one would trigger a claim. If the answer to any of them is no, you have identified a gap worth addressing before it becomes a loss.

Tooher-Ferraris reviews commercial insurance programs with exactly this kind of scenario-based analysis. For businesses with complex vendor or technology dependencies, our risk management consulting approach helps identify where your current program has structural gaps and what coverage options exist to fill them. Learn more about specialty programs that address non-standard and emerging exposures.

The Insurance Information Institute publishes detailed guidance on contingent business interruption coverage at III.org, and RIMS.org maintains current risk management resources for business continuity planning.

Ready to find out whether your business interruption coverage would actually respond when you need it? The team at Tooher-Ferraris has been helping businesses close coverage gaps since 1932. Contact us today at https://toofer.com/contact-us/ to schedule a no-obligation consultation.

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