Recent socio-technical developments caused by ongoing digitalization (e.g., robotic process automation, artificial intelligence, anthropomorphic systems) or the COVID-19 pandemic (e.g., an increasing number of remote working employees and hence, increasing number of virtual collaboration) change the work environment and culture. Digital and smart workplace technol-ogies facilitate business processes and provide tools for efficient communication and (virtual) collaboration, “increasing the productivity of the workforce in the information age” (Attaran et al. 2019, p. 1). Especially in times of the COVID-19 pandemic, digital technologies play a crucial role in keeping us socially close, connected, and collaborative while increasing the phys-ical distance between humans. However, this development affects the health of employees (Tarafdar et al. 2013). In research, for example, it has long been known that the increased usage of digital technologies and media (DTM) may cause stress, leading to potentially harmful reac-tions in individuals. Research has noted this specific form of stress as technostress (Ayyagari et al. 2011; Tarafdar et al. 2007; Tarafdar et al. 2011; Tarafdar et al. 2019), which is an umbrella term for causes, negative organizational outcomes, and negative humanistic outcomes resulting from the use of DTM at work. The simultaneous consideration of humanistic (e.g., well-being, equality) and organizational outcomes (e.g., efficiency, productivity) is an integral part of a socio-technical system (Beath et al. 2013; Mumford 2006), which is at the core of the IS discipline (Bostrom et al. 2009; Chiasson and Davidson 2005). However, a review from Sarker et al. (2019) regarding published research articles in one of the top journals within the IS community revealed that most reviewed studies (91%) had focused exclusively on instrumental goals. They conclude that “many IS researchers have forgotten or ignored the premise that technologies need to benefit humankind overall (Majchrzak et al. 2016), not just their economic condition” (Sarker et al. 2019, p. 705). Especially as humanistic outcomes can lead to even more positive instrumental outcomes. Hence, Sarker et al. (2019) call for focusing on the connection between humanistic and instru-mental outcomes, enabling a positive synergy resulting from this interplay. For this reason, this dissertation adopts a socio-technical perspective. It aims to conduct re-search that links instrumental outcomes with humanistic objectives to ultimately achieve a healthier use of DTMs at the digital workplace. It is important to note that the socio-technical perspective considers both the technical component and the social component privileging nei-ther one of them and sees outcomes resulting from the reciprocal interaction between those two.Therefore, the dissertation focuses on the interaction while applying pluralistic methodological approaches from qualitative (e.g., semi-structured interviews, focus group discussions) and quantitative research (e.g., collection from a field study or survey research). It provides a theo-retical contribution applying both behavioral research (i.e., analysis of cause-and-effect rela-tionships) and design-oriented research (i.e., instructions for designing socio-technical information systems). Overall, this work addresses four different areas within the reciprocal interaction between the social and technical components: the role of the technical component, the role of the social component, DTMs fostering a fit between the technical and social compo-nents, and the imminent misfit between these two due to ongoing digitalization. First, to contribute to an understanding of the technical component’s role, this thesis presents new knowledge on the characteristics and features of DTM and their influence on employee health and productivity. Research on the design of digital workplaces examined different design approaches, in which information exchange and sharing documents or project support were regarded (Williams and Schubert 2018). However, the characteristics of DTM also play an es-sential role in the emergence of technostress (Dardas and Ahmad 2015). This thesis presents ten characteristics of DTM that affect technostress at an individual’s workplace, including a measurement scale and analysis on how these characteristics affect technostress. Besides, also, the provision of functional features by DTMs can affect instrumental outcomes or humanistic objectives. For example, affording users with certain kinds of autonomy regarding the config-uration of DTM while they work towards their goals could have a tremendous effect on pursu-ing goals and well-being (Patall et al. 2008; Ryan and Deci 2000). Therefore, this thesis presents knowledge regarding the design of DTM on the benefits of affording users with autonomy. Furthermore, it shows that merely affording more autonomy can have positive effects above and beyond the positive effects of the actualization of affordance. Second, to contribute to an understanding of the social component’s role, this thesis presents new knowledge on contextual and individual factors of social circumstances and their influence on employee health and productivity. In this context, the influence of the COVID-19 pandemic on the intensity of technostress among employees is considered, as work became more digital almost overnight. Therefore, this thesis provides empirical insights into digital work and its context in times of the COVID-19 pandemic and its effect on employees’ well-being, health, and productivity. Furthermore, measures to steer the identified effects if the situation in the course of the COVID-19 pandemic persists or comparable disruptive situations should re-occur are discussed. On the other hand, this research takes a closer look at the effect of an individual preference regarding coping styles in dealing with upcoming technostress. A distinction is made between the effects of two different coping styles, namely active-functional and dysfunctional, on strain as a humanistic outcome and productivity as an instrumental outcome. In the course of this, evidence is provided that coping moderates the relationship between the misfit within the socio-technical system and strain as proposed by the psychological theory of job demands-resources model (Demerouti et al. 2001). Third, to contribute to a successful fit between the technical and social components, this thesis presents frameworks and guidelines on the design of DTM, which understand the social com-ponent (here the user and her/his environment) and adjust accordingly to the needs of their users. Therefore, the thesis provides knowledge on the design of DTMs that support users in applying stress management techniques and build the foundation for stress-sensitive systems (i.e., systems that aim to mitigate stress by applying intervention measures on the social and technical component (Adam et al. 2017)). As a matter of fact, a framework for collecting and storing data (e.g., on the user and her/his environment) is developed and experiences with im-plementing a prototype for life-integrated stress assessment are reported. The experiences from this and the existing knowledge in the literature will finally be aggregated to a mid-range design theory for mobile stress assessment. To contribute to the fourth and last aspect, the imminent misfit within the socio-technical sys-tem due to ongoing digitalization, this thesis presents new knowledge regarding digital work demands that potentially affect both employees’ health and instrumental outcomes. The current version of technostress’s theoretical foundation was introduced more than ten years ago by Tarafdar et al. (2007). However, the interaction with and use of DTM has considerably changed along with the societal and individual expectations. Therefore, this thesis puts the current con-cept of technostress to test. As a result, a new theory of digital stress, as an extension of the concept of technostress, is proposed with twelve dimensions – instead of five dimensions within the concept of Tarafdar et al. (2007) – that could be hierarchically structured in four higher-order factors. This theory holistically addresses the current challenges that employees have to deal with digitalization. To sum up, this dissertation contributes to the IS community’s knowledge base by providing knowledge regarding the interaction between employees and their digital workplace to foster the achievement of humanistic and instrumental outcomes. It provides both behavioral research and design-oriented research while using pluralistic methodological approaches. For this pur-pose, this thesis presents knowledge about the different components within the socio-technical system, design knowledge on DTMs fostering the fit between these components, and an under-standing of an upcoming misfit due to the ongoing digitalization. Overall, this research aims to support the successful change towards a healthy digital workplace in the face of digitalization.