This study investigated computer users’ help-seeking behaviors within the context of accomplishing a novel and challenging computer task. In addition, this study examined how different help-seeking behavioral variables relate to both personal factors and outcome measures in an exploratory manner. Finally, a structural model examined the effect of personal factors on task performance through the mediating function of help-seeking effectiveness. A total of 67 undergraduate students participated in the study. Participants were asked to perform a challenging task in Microsoft Word. The usability software MORAE was used to record the interactions between participants and computer systems. Participants had access to five help sources: “F1 help,” “reference book,” “the Web,” “video tutorial,” and “lab assistant,” which differ in media type (electronic vs. non-electronic) and interactivity levels (high vs. low). This study found that participants showed a wide range of help-seeking behaviors. Some participants were more active in seeking help than others. Participants also engaged in different help-seeking patterns when using different help sources. A dominant help-seeking strategy was to stay with the same source used in the previous help-seeking episode. Help-seeking behavior affected task performances, but personal factors had no significant effect on help seeking or task performances. Based on the findings, the research value of this study, its practical implications, its limitations, and future research directions are discussed.