Technostress is conceptually defined as a modern-day disease of adaptation which is associated with the inability to adopt, implement, and use new computer technologies in a healthy manner. Technostress can be categorised into five dimensions, collectively known as techno-stressors: technology overload, invasion, complexity, insecurity, and uncertainty. Researchers often describe technostress as negative, or the “dark side” of technology. A broader review of the related literature, however, suggests that technostress has both a “bright” and a “dark” side. The aim of this chapter is to provide in-depth, holistic insight into technostress, which encompasses both the positive and negative components of technostress. A qualitative approach was followed, making use of a systematic review of contemporary research on the themes of the bright and dark sides of technostress, which allowed the author to evaluate documented research on the topic. If technostress indeed has both bright and dark sides, that means it cannot solely be viewed in a negative light. The holistic approach which the author adopted, emphasises the role of those components which are embedded in both subprocesses of technostress—techno-eustress and techno-distress—which differs from extant research in that it highlights how technostress unfolds based on cognitive appraisal. In this chapter, the challenges and hindrances associated with technostress are outlined, as are the indicators of the eustress and distress subprocesses within a technological context, as well as the variables that may accentuate positive psychological states, or “savour eustress”.