This paper examines how and why employees used online computer access to commit fraud in New Zealand small businesses. Drawing on data from 18 court documents between 2006 and 2020, we use document analysis to examine the pressure, opportunity, rationalization, and capability elements using the fraud diamond framework. We provide three major findings. First, the employee frauds were motivated by vice and family circumstances. The combination of opportunity and capability had a devastating effect on the length of the fraud and the amount of financial loss. Second, the frauds were mostly perpetrated by middle-aged women in both managerial and nonmanagerial positions who displayed unusual behaviour but had no prior convictions. Third, small businesses are vulnerable to fraud in their billing, accounts payable, and payroll systems; thus, relevant prevention strategies are recommended. Overall, we conclude that the tendency for fraud is heightened in small businesses where trusted employees: have multiple responsibilities; have an occupational position that provides them with opportunity; are capable of manipulating online access; and have external pressures of addictions or adverse family circumstances. Our multiple cases approach facilitates a better understanding of the employee fraud contexts, including the motivation and the methods employed to commit such fraud in New Zealand.