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It is generally recognized that offenders tend to diversify the criminal activities in which they are involved. However, recent research suggests that versatility bouts are often interspersed by episodes of specialization. Although these findings justify that criminal specialization/versatility must be considered as a dynamic feature, little is known about the factors influencing trajectories of criminal diversification. Embedded within the criminal career paradigm, the present study aims to examine whether different offending versatility trajectories exist among a sample of 150 offenders incarcerated in five penitentiaries located in the province of Quebec, Canada. Based on group-based trajectory modeling, results reveal the presence of distinct diversification trajectories among offenders. The impact of both static and dynamic factors on versatility trajectories is also evaluated. Findings indicate that criminal networks’ characteristics predict diversification trajectory, whereas factors reflecting criminal propensity such as age at first crime and low self-control do not. Time-varying local life circumstances, such as legitimate employment and living with spouse/girlfriend, as well as monetary criminal efficacy are also found to influence offending versatility over time. The potential impact of these results on developmental and life course theoretical perspectives is discussed.