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Artificial Intelligence (AI) capabilities are being developed to provide automated, 24/7 monitoring of trucking fleets and vehicle maintenance. Trucking leaders have a mixed reaction to this technology, with some being enthusiastic and others taking a wait-and-see approach. Bill Bliem and Andrew Erin, two trucking leaders, have seen real gains from AI-powered fleet maintenance software and modern telematic systems, respectively. These systems provide more precise and prescriptive information to enhance the diagnosis process and provide decision-makers with information and tools that lead to more uptime and fewer breakdowns.