Background <p>Mindfulness has made its way into the business context. Simultaneously, several options for digitally encouraging mindfulness have been proposed in recent years, with opposing opinions questioning the compatibility of mindfulness and technology, claiming it is a paradox. This study aims to examine the compatibility of mindfulness and technology, i.e., how mindfulness and digitalization interact as compatible or incongruous phenomena in the digital working context.</p> Methods <p>Semistructured interviews with 15 experts, all specializing in technology and mindfulness in the workplace, were conducted to generate hypotheses of digital mindfulness at work. Qualitative content analysis as well as content analysis via extraction were utilized in this study to explore mutual relationships.</p> Results <p>Information about workplace mindfulness, digitalization, technology and digital stress was synthesized. The themes “Mindful by Workplace-Design” (a) and “Working Mindfully in a Digital Cooperation” (b) resulted in suggested modifications for digital workplaces. The compatibility of the two phenomena escalated at the “Tipping Point” (c), reached beyond the use of mindfulness apps, i.e., when wearables are added.</p> Conclusions <p>The results point out the limits of digital mindfulness, as well as opportunities for the cooperation of mindfulness and technology. For employers, this study provides guidance for shaping mindful digital workplaces and mindful work cultures.</p>