Technology integration in the workplace context has led to substantial growth in high- versus low-skilled jobs, and thus, further disparities between workers and those who were already unemployed. Technology use is also being used more frequently in the job search process, which could further lead to disparities, especially for job seekers experiencing marginalization. Thus, we conducted a controlled longitudinal field deployment of two employment-based tools—RevueCV and InterviewApp—among 46 Switzerland-based unemployed job seekers. Using the theory of planned behavior (TPB), we sought to understand how the tools affected job search self-efficacy, subjective norms and job search attitudes—the three factors that influence a job seekers’ job search intention. Although participants appreciated the support the two tools provided, and the inherent study benefits, our interview and survey results showed no substantial changes in their TPB values, primarily because the tools provided overlapping services with the local job placement offices. However, results of our interviews found autonomy, or the lack thereof, to be a key factor contributing to job seeker dissatisfaction. We introduce the concept of self-regulation to the TPB as an explanatory construct and contribute design and theoretical implications to support autonomy among job seekers with less control of their job search.