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On December 25, 2021, at 12:20 UTC, the James Webb Space Telescope lifted off and onward to its destination in orbit at the second Lagrange point. With more than two decades in development, and an international collaboration between NASA, CSA, and ESA, Webb is one of the most anticipated science missions ever launched. After a dramatic and flawless launch, Webb's toughest and riskiest days lie ahead. Unprecedented in its complexity and ambition, over the next two weeks Webb would undergo the most complex on-orbit deployment sequence ever attempted, with any single deployment anomaly carrying the risk of full mission failure. An exquisite design, years of ground testing, a exhaustively trained and rehearsed operations and engineering team, and an unprecedented level of contingency planning, all resulted in a fully and successfully deployed Webb observatory, on its way to L2, and nominally cooling to its cryogenic temperatures. Although Webb still had many more months of commissioning left, there was a collective sigh of relief heard round the world. This incredible achievement was not by chance but was years in the making. We go behind the scenes of Webb's first month on orbit, starting with the unique and challenging launch itself, the time criticality of its mid-course corrections, and a summary of nearly 14 days to undergo nearly 50 major deployments. We discuss what went better than planned and how years of robust and detailed contingency planning were prepared for unanticipated events and on-orbit spacecraft behavior. And finally, we provide a brief overview of the entire commissioning process which successfully completed on July 10th, 2022.