Employees’ non-malicious counterproductive computer security behaviors (CCSB) at work could put organizations’ information-related assets at risk, if unchecked. Using concepts from the social cognitive and organizational citizenship behavior (OCB) theoretical frameworks, this study examined the effects of observational learning/modeling, social support, and OCB (i.e., helping behaviors and civic virtue) on employees’ desire to indulge in CCSB. A research model including the aforementioned factors was proposed and tested using the partial least squares (PLS) technique. A survey of Canadian professionals’ opinions was used. The result did not affirm the relationship between employees’ observational learning/modeling and intentions to engage in CCSB. The results, however, confirmed that social support and OCB (i.e., helping behaviors and civic virtue) have significant negative effects on intentions to engage in CCSB, which, in turn, has a significant positive effect on employees’ self-reported indulgence of CCSB at work.