There is an increasing number of older adults being encouraged to come back to the workforce in search of better financial security in their later years. At the same time, the job market nowadays has increasingly depended on technology to recruit new workers, especially in Smart Cities, a concept that has been recently introduced to developing countries. As a result, the use of the Internet for job searches has become increasingly important for older adults living in urban environments, especially those with limited resources. However, there has not been an in-depth paper exploring the various factors that may affect the older population’s ability to use this new development to their advantage. This study offered a closer look at the social and economic factors that influence acceptance of using the Internet to look for a job among older urban poor in Thailand. By understanding the influences that shape their attitudes and behaviors towards online job searches, it is then possible to guide the development of Smart Cities and offer better assistance to older adults who wish to use the Internet for employment opportunities. We applied a logit regression model on data collected from individuals aged pre-retirement and retirement (n = 1505) in two Thai cities with significantly different economic development levels. The results showed that gender, religion, family arrangement, and income had a significant impact on older adults’ online job search activities, especially when it came to women, people of the Islamic faith, people living with partners, and high-income individuals. Urban planners are recommended to take these aforementioned factors into account while formulating the Smart Cities development plan.