Agile transformation, once heralded as the panacea for organizational agility, often meets unexpected hurdles that impede its success. Almost all agile initiatives inevitably ask the following questions during the lifecycle of an agile transformation: Have we chosen the correct framework? Is the organization ready for the transformation? Are our product owners, and agile coaches effectively skilled to play their roles? Can we achieve these outcomes in this timeframe? Drawing parallels with the seven deadly sins from ancient doctrine, this abstract presents 5 most commonly overlooked “sins” that identifies and addresses the critical pitfalls hindering agile transformations. From prideful overconfidence in the scrum master’s omnipotence to slothful complacency in the product owner’s decision-making – and unveils their adverse impacts on agile initiatives. By understanding these sins and their manifestations within organizations, leaders can devise proactive strategies to mitigate risks, foster a culture of continuous improvement, and steer their agile transformations towards sustainable success.