Agile methods have co-evolved with the onset of rapid change in software and systems development and the methodologies and process models designed to guide them. Conceived from the lessons of practice, Agile methods brought a balanced perspective between the intentions of the stakeholder, the management function, and developers. As an evolutionary progression, trends towards rapid continuous delivery have witnessed the advent of DevOps where advances in tooling, technologies, and the environment of both development and consumption exert a new dynamic into the Agile oeuvre. We investigate the progression from Agile to DevOps from a Critical Social Theoretic perspective to examine a paradox in agility – does an always-on conceptualization of production forestall and impinge upon the processes of reflection and renewal that are also endemic to Agile methods? This paper is offered as a catalyst for critical examination of and as a call to action to advocate for sustaining and nurturing reflective practice in Agile and post-Agile methods, such as DevOps. Under threat of disenfranchisement and relegation to automation, we question how evolution towards DevOps may alter key elements in the tenets and principles of the Agile methods phenomenon.