Although counterproductive work behaviour towards the organization (CWB-O) or supervisors (CWB-S) is commonly treated as a reaction to psychological contract breach (PCB), we propose that the PCB-CWB relationship is recursive and that CWB may increase the likelihood to perceive PCB through its effects on self-esteem and subsequently on organizational cynicism. By estimating a two-level time-lagged mediation model on daily data from 103 US employees (904 observations), we found evidence for this hypothesized chain of events. These findings demonstrate that PCB and CWB happen with reference to past perceptions of PCB and/or CWB and future anticipations of PCB and/or CWB. We discuss suggestions for future research and novel practical implications in preventing further escalation.