A 2x2 enhanced Wizard-of-Oz experiment (N = 32) was conducted to compare two different approaches to presenting information to drivers in easy and difficult driving conditions. Data of driving safety, evaluation of the spoken dialogue system, and perception of self were analyzed. Results show that the user-modeled summarizeand-refine (UMSR) approach led to more efficient information retrieval than did the summarize-and-refine (SR) approach. However, depending on driving condition, higher efficiency did not always translate into pleasant subjective experience. Implications for usability testing and interface design were presented, followed by discussions of future research directions. Author Keywords Information presentation, spoken dialogue system, user modeling, driving simulator, context of use, usability testing. ACM Classification Keywords H.5 Information interfaces and presentation; H.5.2 Usercentered design; I.2.1 Natural language interfaces.