As more and more organizations undertake digital transformation they become increasingly dependent on their online presence. This exposes their business to cyber-attacks that target the growing number of vulnerabilities in web services software stacks, which require the organizations to evolve their current cyber defense approach and stretch their resources. Navigating digital transformation securely can feel overwhelming for some organizations. In this talk, we will present several real-world case studies showing how things can go wrong and examine strategies for undertaking this journey securely.