In investigating older adults’ perspectives on ITS related to public transportation, the effect of personal control over ITS use is explored across three scenarios: video surveillance in public transportation, real-time travel information, and a personal, pedestrian navigation system with public transportation information. Swedish respondents’ perceptions indicate neutral effects on privacy and positive effects on one’s sense of assurance across the scenarios, particularly in situations perceived as more vulnerable, such as using the subway and traveling alone or in an unfamiliar setting. Of the three technological applications, video surveillance (CCTV) elicits the most favorable responses, although this does not directly translate to perceived personal benefit, where real-time information is rated the highest. The navigation system is generally ranked relatively lower for effects on assurance, although this pattern is broken for car and walking modes; modes in which the navigation function may be prioritized. Thus, personal control over aspects of the trip, rather than personal control over ITS use, better explains the responses, as ITS can serve to reduce (perceived) uncertainties, improving one’s sense of assurance. Significant differences are found for gender, but not for further age stratification. Overall, female respondents feel relatively less assured when traveling and rate the technological applications’ effects on their assurance more highly than men. Although men express a greater personal interest in technology, it appears that there is more potential for women to positively benefit from technology in terms of greater perceived assurance while traveling. This calls into question the possibilities of effectively addressing user needs or concerns, especially via technologies intended for individual use, if those who potentially serve to gain more by them are not being reached or are not as interested in such “solutions”.