Congestion at urban and active railway level crossings leads to non-compliant driver behavior, and scenarios in which road users may enter into the rail corridor with the crossing nearing full closure. Previous research indicates this scenario occurs with alarming regularity during peak periods. However, limited research has investigated whether such non-compliance arises from errors or from deliberate decisions. The objective of this study was to better understand driver decisions when approaching a level crossing during activation. Vehicle movements and crossing activation were continuously recorded for 2 months at a congested active level crossing close to Melbourne, Australia. Each movement corresponding to a vehicle approach to the level crossing during onset of activation was extracted with traversals counted, and the ability to stop safely modeled with linear motion equations, using the position and speed of the vehicle at activation. The probability of entering the level crossing was then modeled with generalized linear models. Analysis revealed that much of the non-compliance was involuntary and linked to a dilemma zone in the absence of sufficient warning time for drivers to react to and safely stop before proceeding through the crossing. However, deliberate non-compliance was also an issue, and independent of the time of day. Findings are discussed in relation to the ideal grace period for road users at such crossings, and consideration is given to enforcement as a viable treatment for reducing deliberate non-compliance.