Firms operating in complex and transient environments face enormous challenges due to several factors, including rapid changes in the business environment, short-term product life cycles, fast development in information technology, and increasingly demanding but less loyal customers with fierce competition. Strategic flexibility allows a firm to respond promptly to market challenges and opportunities. The primary objectives of the chapter are to identify the vital technology-related drivers of flexibility in e-business and the significance of flexibility, as well as to analyse how organisations can leverage flexibility as a competency for businesses, especially e-businesses. The chapter also attempts to outline the complexities and dynamics involved in IT adoption by incorporating factors such as organisational readiness assessment, risk analysis, implementation roadmap, and monitoring and evaluation. Furthermore, the chapter delves into the various challenges and complexities organisations encounter in cultivating flexibility, ranging from resistance to change to the difficulty of balancing stability with agility.