Organizations facing high risks and operating in purely digital domains, such as computer security and many financial services, must meet two, contradictory goals: they need to identify digital threats at scale and speed while also avoiding errors that result from automated processing. Research on high-reliability organizations has identified multiple challenges in reaching these goals simultaneously, because automation often renders organizations’ operations “mindless” and unable to cope gracefully with changing, complex situations characteristic of high-risk domains. In digital operations, a special challenge arises from the “frame problem” connected with the inability of algorithms to adapt to environments not identified within their developers’ initial cognitive frames. An exploratory, theory-generating case study was conducted within a computer security company (F-Secure) to examine how organizations acting in digital domains may achieve high reliability by mitigating the frame problem. This article examines digital organizing of the epistemic and pragmatic features of operations, along with arrangements of these features that respond to the frame problem. Collective mindfulness is identified as emerging in such a sociotechnical setting via a carefully layered, systemic constellation of (human) mindful and (digital) mindless operations while the organization’s core operations remain digital and algorithmic. The findings point to heretofore unexplored reliability challenges associated with digital organizing, alongside several relevant ways to overcome and/or mitigate them.

Organizations replace their legacy systems for technical, economic, and operational reasons. Replacement is a risky proposition, as high levels of technical and social inertia make these systems hard to withdraw. Failure to fully replace systems results in complex system architectures involving manifold hidden dependencies that carry technical debt. To understand how a process for replacing a complex legacy system unfolds and accumulates technical debt, we conducted an explanatory case study at a local manufacturing site that had struggled to replace its mission-critical legacy systems as part of the larger global company’s commercial-off-the-shelf (COTS) system implementation. We approach the replacement as a sociotechnical change and leverage the punctuated sociotechnical information system change model in combination with the design-moves framework to analyze how the site balanced creating digital options, countering social inertia, and managing (architectural) technical debt. The findings generalize to a two-level (local/global) system-dynamics model delineating how replacing a deeply entrenched mission-critical system generates positive and negative feedback loops within and between social and technical changes at local and global levels. The loops, unless addressed, accrue technical debt that hinders legacy system discontinuance and gradually locks the organization into a debt-constrained state. The model helps managers anticipate challenges that accompany replacing highly entrenched systems and formulate effective strategies to address them.