While technological readiness is crucial in today’s digital work environment, its impact on employee health is nuanced and depends on various factors. The common belief is that by fostering a positive attitude towards technology, individuals can not only enhance their professional capabilities but also support their health. We challenge this assumption and ask whether and under which conditions technological readiness has beneficial effects on employee health. We argue that, in specific organizational contexts, technological readiness can lead to emotional exhaustion; specifically, we introduced a three-level, three-way interaction between individual-level technological readiness, unit-level formalization, and firm-level management boundary control and tested it on 2,267 employees nested into 1,547 units in 80 German organizations. We found that technological readiness can represent either a burden or a blessing for employees, depending on the interplay of contextual factors which cannot be considered in isolation. Specifically, technological readiness can lead to increased emotional exhaustion when not supported by formalization and management boundary control. Alternatively, it is beneficial for an individual’s health when supported by these factors. As such, our study offers an integrative understanding of the antecedents of emotional exhaustion and their interplay, rather than considering single factors. Practically, we guide organizations on how to create an environment that fosters the positive effects of technological readiness. This holistic approach ensures that the workforce is well-prepared to leverage new technologies effectively and sustainably.