Manhattan’s historic Central Business District Tolling Program is officially live, hitting commuters with an initial $9 peak-period toll. But behind the political headlines lies a massive operational and technological experiment. From the high-stakes data-sharing dance between the MTA and Port Authority to deploy “crossing credits,” to the mixed success of shifting heavy freight traffic via overnight discounts, and the deployment of advanced Edge AI to crush license plate fraud—New York is writing the definitive playbook for the future of urban road pricing. Here are the critical operational triumphs and roadblocks emerging from the grid.