Detaching from work is beneficial because it helps employees recover from work demands. However, we argue that detachment may be a trade-off for employees in organizations with higher (vs. lower) levels of performance pressure. Drawing on social self-preservation theory, we hypothesize that evening detachment leads employees working in higher (vs. lower) performance pressure work contexts to experience increased shame at work the next morning. In turn, we hypothesize that shame motivates employees to engage in cheating behaviors to covertly inflate their performance and reduce the possibility that others will form negative perceptions of them. In three studies—a 2-week experience sampling study and two experiments—we find that evening detachment leads to heightened next-morning shame in higher (vs. lower) performance pressure work contexts, increasing cheating behavior throughout the workday.