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Travel-based multitasking, or the performance of activities while traveling, is more feasible than ever before, as the expanding availability of shared ride services and increasing vehicle automation coincide with the ubiquity of portable information and communication technology devices. However, the question of whether, and if so, how these increasingly blurred boundaries between activities are truly helping rather than hurting us is not presently well-understood. Using an attitudinally-rich travel survey of Northern California commuters (N≈ 2500), we develop a conceptual and empirically-based framework for studying benefits and disadvantages of travel-based multitasking. Through latent variable models of reported benefits and disadvantages of activities conducted on a recent commute, we identify constructs associated with hedonic and productive benefits, and with affective and cognitive disadvantages. This empirically-developed framework informs the definition of binary variables indicating the presence/absence of each construct for a given traveler on the commute in question. We then present two bivariate binary probit models that examine the effects of person and trip attributes such as personality traits, chosen mode, commute preferences, and activities conducted while traveling on the presence of those benefits and disadvantages, respectively. Notably, we find evidence that conditions/activities that may facilitate multitasking benefits can also simultaneously yield disadvantages; for example, several activities–conspicuously including talking on or otherwise using a phone–increase the probability of receiving benefits while also …