Cyber resiliency is the ability to anticipate, withstand, recover from, and adapt to adverse conditions, stresses, or compromises on systems that use or are enabled by cyber resources. This operational definition adopted from the National Institute for Standards and Technology in Special Publication 800–160 Volume 2, goes beyond technical implementation to include how an organization responds and recovers to adverse effects on information systems; within that response is the ability to continue or fail-over critical system functions even while the system itself is under duress. This chapter presents recommendations for overcoming and adapting to leadership and socio-technical challenges in adopting cyber resiliency. The authors use the 2021 Colonial Pipeline cyber incident to illustrate socio-technical influence factors and make several deductive observations of publicly available information following the incident. The authors make several recommendations for practitioners based on the deductive conclusions drawn from the incident and a 2023 study exploring limiting and enabling factors toward cyber resiliency adoption in organizations based on the Diffusion of Innovations Theory.