For employees, work involves taking breaks as well as engaging in specific required duties, and sometimes that break taking is construed as “cyberslacking” by employers. After historical treatments of cyberslacking concepts, this article analyzes ways that artificial intelligence (AI) methodologies and the “bossware” platform genre are aiding management to counter the cyberslacking phenomena directly exhibited by employees or projected from previous activities and profiles. It contrasts straightforward “policing” methods that aim toward the identification of cyberslacking instances for selective punishment through surveillance, with “predictive cyberslacking” approaches that profile certain trends and patterns in employee behavior. Such identified inclinations can be used to engage or nudge workers into specific, individualized patterns of work and approved recreational or developmental activity. A medicalization-style approach is often used in bossware to entice employees toward particular mental health-themed activities (including mindfulness and meditation activities).