Digital transformation has become a driving force for many organizations. The pace of these transformations is accelerating and is moving towards the necessity of continuous adaptability. Kane (2017) has noted that digital transformation is not a “singular process” but is instead an ongoing process of adaptation. Two popular methods of information systems development and implementation—Agile development (Erickson et al., 2005) and DevOps (Siau et al., 2022)—have shaped the broad approaches to digital transformation. The overarching goal of each approach is “to deliver better solutions faster,” yet each has a different emphasis. Agile approaches deliver value by emphasizing substantial, persistent customer involvement in designing and refining products through adaptable, flexible, iterative, and incremental development efforts. DevOps seeks a similar integration of people by encouraging a more robust collaboration between developers and the operators who implement and maintain the systems (i.e., an endto-end perspective) including the application of automated tools to support and streamline the development process. Although both approaches are in widespread use with visible benefits that can be achieved, challenges remain in the consistent application of the methods and tools across the development process. Experience suggests that the two approaches are often complementary in application, with each approach buttressing some of the gaps or limitations of the other approach in the development, delivery, and implementation of software products. Current research evidence is inconsistent and lacking. In this research, we perform a systematic analysis to compare and contrast Agile and DevOps in developing systems to accelerate and support digital transformation. A preliminary study shows that the strengths to be analyzed include: (i) the acceleration of development cycles and improved time-to-market; (ii) the creation of reliable, quality products that meet customers’ needs; (iii) the reduction of production costs and enhancing cost efficiency; (iv) enhanced security, testing, and UX practices; (v) better team efficiency and motivated staff; and (vi) the nurturing of teams of Agile and DevOps experts. In addition to these strengths, several challenges being examined include: (i) the technical challenges during transition; (ii) the work culture challenges during transition; (iii) the time needed for the transition; (iv) the lack of talent and expertise; and (v) security and testing issues for the software products. Other dimensions for comparison include cognitive (Siau & Wang, 2007) and communication (Siau & Tan, 2005) issues. The research also discusses the future development of Dev*Ops (e.g., DevSecOps) with respect to the unique characteristics of digital transformation. This research is ongoing.