When the Agent AI tool wiped out small businesses’ databases and their backups, and later admitted that it had “violated every given principle,” it couldn’t help but give some people heartburn about the pace of change when it comes to artificial intelligence.
PocketOS, which primarily develops software for car rental companies, used an AI coding tool called Cursor. The AI agent was working on a mundane task when it decided to “solve” the problem by deleting the company’s data.
After the database disappeared, PocketOS asked Cursor to explain what happened.
The AI agent reportedly responded by saying, “It guessed instead of verified. It carried out destructive actions without being asked. It didn’t understand what it was doing before it did it.”
This and similar articles reported by multiple sources should leave trucking executives (and leaders in all types of businesses) wondering how far they can trust artificial intelligence.
Fleet executives now feel caught between two fears: trusting AI too much or not embracing it quickly enough.
How do you find the middle ground? How do you navigate the sea of potential AI applications and find the best fit for your business?
Few industries are better suited to AI than trucking. Fleets operate on slim margins while managing massive data streams, operational complexity, and constant pressure to improve efficiency.
However, these same factors may make trucking vulnerable to overestimating the promise of AI and increasing the risk of cyberattacks and rogue AI agents.
Why AI is transforming trucking
At the 2026 Advanced Clean Transportation Expo, fleet executives repeatedly described AI as a once-in-a-generation technology shift and compared its potential impact to electricity, horse-drawn carriages, and other breakthrough innovations.
“I don’t think we realize the incredible opportunity that AI has yet,” said Paul Rosa, senior vice president of procurement and fleet planning at Penske Truck Leasing. “I don’t think we’re even close to 5% of what AI can do in the transportation industry.”
AI’s ability to process large amounts of information opens up opportunities to make data-driven decisions at a scale and speed that humans cannot match.
Why truckers can’t wait for perfect AI
But with that enthusiasm came another message. Trucking companies cannot afford to wait for a perfect system or complete certainty before they start adapting.
Austin Henderson, chief information officer at FirstFleet, a private airline that Werner acquired earlier this year, urged fleets to focus less on futuristic end goals and more on practical steps they can take now to modernize systems, improve data quality and prepare for increasingly AI-driven operations.
“If you wait for perfection, the opportunity will pass you by, and you will wake up and realize that your competitors, your peers in the field, already exist.”
How truckers are already using AI
AI is no longer theoretical and the pressure to adapt is increasing. Vehicle companies are already using this in ways both visible and invisible to drivers and customers.
“AI can be incredibly complex, and I feel like it has gone through this hype cycle,” said Shelley Sanger, executive vice president of strategy and marketing for Penske Transportation Solutions.
“But we’re also in this very exciting place, where we’re seeing some very real applications of AI.”
Some of the earliest AI-driven applications in trucking came in areas like in-cab cameras and predictive maintenance. Today, you can play a role in all aspects of trucking operations.
A Fleet Advantage study released during the National Commercial Trucking Council’s 2026 Annual Conference and Exhibition found that generative artificial intelligence is rapidly becoming a mainstream tool among commercial fleets. However, weak data infrastructure and limited measurement capabilities prevent many organizations from realizing deeper benefits.
Generative AI’s rapid rise is one of the largest year-over-year changes the company has recorded in its annual survey. The technology sector did not appear at all in the company’s 2025 study.
When AI brings unexpected benefits
Werner Enterprises has leveraged AI for tasks such as freight acceptance, managing driver recruitment and retention efforts, optimizing routes and driver time-in-service, and proactive maintenance modeling.
“There may be additional benefits that you don’t necessarily see in the first flash of AI,” said Daragh Moran, executive vice president and chief information officer at Werner.
For example, the fleet recently introduced AI tools to schedule package pickups and deliveries. Rather than having your staff make thousands of phone calls each week, AI tools make the calls and use APIs to schedule appointment times.
The result was more than just labor savings. Better appointments lead to better asset utilization, with trucks moving faster, unloading faster, and more time spent generating revenue.
“We just got the best possible reservation for our truck,” he said. “Honestly, we were thinking about it beforehand, but we didn’t think it was really starting to have an impact.”
Where AI can fail
Ben Wilkens, NMFTA’s chief cybersecurity engineer, recently wrote an article for Heavy Duty Trucking about how AI is changing the cybersecurity landscape. It wasn’t just about how bad actors were using AI to infiltrate fleet operations. It was also about the exact problem PocketOS encountered:
“How do we manage the identity of an agent with the skills of an expert and the blind enthusiasm of an overzealous intern who lacks the experience to know better?”
Werners Mahon said: “We have to look at AI as a very powerful application. As the saying goes, with great power comes great responsibility. And all you have to do is take that extra step every time and think, ‘How can AI make things better, how can it increase efficiency, how can it increase productivity?’
“‘How can we use this powerful tool for good? How can we avoid making bad decisions?'”
“Basically, it’s allowed us to be faster and make better decisions. And in the long run, I think it’s going to become a natural part of the job.”
AI is a tool, and how we deploy and use it is critical.
AI is prone to hallucinations and wrong decisions. This can expose companies to further cybersecurity challenges and intellectual property issues. Requires appropriate data to use. If you’re tracking maintenance on a whiteboard, that might be the problem.
And AI requires human oversight. AI agents need proper guardrails. Employees need training on how best to drive desired results from generative AI tools and how to monitor for errors. Change management is important for introducing your team to AI, how it works, and what it means for your company and their work.
AI cannot replace human relationships
And it’s not just the scary idea of an AI agent going wild inside your computer and deleting your data, or Claude or ChatGPT hallucinating or giving you false information. Just like a hammer, AI may not be the best tool for every situation.
For example, AI tools can help vehicles communicate with drivers to handle routine requests. If the time saved for driver managers is used to actually communicate with drivers, it can have real value. However, too much communication with real humans can cause issues with driver retention.
Trucking is a human relations business. If you’re using AI to write all your emails, are you really building or maintaining relationships? If you’re not careful, you could lose the spark of your true personality.
How fleets should approach AI adoption
Just like we’ve been advised for years about where to start with the vast amount of data available to fleets, AI also focuses first on what you want to do, and then on what AI tools you can use to accomplish it.
It’s not just about what you want to use. It’s about why you want to use it.
AI isn’t going away. It is rapidly permeating every aspect of trucking. Yes, you need to approach it carefully and with purpose. However, if you wait until all concerns are resolved before exploring the possibility of working, you may find yourself unable to catch up.
But the fleets that benefit most may not be the ones that have the most AI implementation. They may be the ones who learn where automation can add value, where human judgment still matters, and how to build guardrails before mistakes become costly.
AI is quickly becoming part of the operational DNA of the trucking industry. The question now is whether fleets can learn how to manage technology before it starts making many decisions.
