This study investigated how situational characteristics typically encountered in the transport system influence drivers' perceived likelihood of engaging in mobile phone multitasking. The impacts of mobile phone tasks, perceived environmental complexity/risk, and drivers' individual differences were evaluated as relevant individual predictors within the behavioral adaptation framework. An innovative questionnaire, which includes randomized textual and visual scenarios, was administered to collect data from a sample of 447 drivers in South East Queensland-Australia (66% females; n = 296). The likelihood of engaging in a mobile phone task across various scenarios was modeled by a random parameters ordered probit model. Results indicated that drivers who are female, are frequent users of phones for texting/answering calls, have less favorable attitudes towards safety, and are highly disinhibited were more likely to report stronger intentions of engaging in mobile phone multitasking. However, more years with a valid driving license, self-efficacy toward self-regulation in demanding traffic conditions and police enforcement, texting tasks, and demanding traffic conditions were negatively related to self-reported likelihood of mobile phone multitasking. The unobserved heterogeneity warned of riskier groups among female drivers and participants who need a lot of convincing to believe that multitasking while driving is dangerous. This research concludes that behavioral adaptation theory is a robust framework explaining self-regulation of distracted drivers.