<p>This article analyzes a set of bossware platforms, examining how the systems’ affordances and rhetorical framings affect how employees interact with management, especially regarding cyberslacking and medicalization concerns. Recent managerial initiatives have framed the “cyberslacker” as a deficient human being, incapable of dealing with waves of external stimuli and workplace demands. This article analyzes how some bossware systems encourage employees to give up their personal control over some deeply private and intimate matters. It contrasts “policing” strategies with more recent predictive and transformative approaches that capture certain trends and patterns in employee work behavior. This “medicalization” strategy is often used to nudge employees toward particular wellness or mental health-themed activities or other approved recreational or developmental initiatives. Many bossware systems attempt to soften the frame of their surveillance efforts by involving wellness and mindfulness themes to “curb” cyberslacking while appearing to provide individualized support for cyberslackers, thus placing the cyberslacking situation into a medicalized context. The article outlines emerging artificial intelligence (AI) dimensions of bossware and how they relate to medicalization themes. With its ostensible “friendliness” and “intelligence,” AI-enhanced bossware often fosters misplaced trust in the aims of the managers who are implementing the systems.</p>