Digital transformation in the medical technology sector is revolutionizing how devices are designed, produced, and delivered. This revolution introduces a complex array of cybersecurity challenges that must be addressed to ensure operational resilience, regulatory compliance, and patient safety. Accordingly, this chapter explores the cybersecurity implications of integrating Industrial Internet of Things (IIoT) devices, adapting legacy systems, and third-party and vendor solutions into manufacturing environments. Further, the chapter examines the vulnerabilities introduced by legacy systems, the risks associated with increased connectivity, and the importance of securing data flows across the lifecycle. Lastly, through best practices, this chapter provides a strategic framework for identifying, assessing, and mitigating cybersecurity risks during digital transformation. Note: Special attention is given to secure communication and the role of data privacy in complex manufacturing ecosystems.