Humans must increasingly partner with automation in complex systems such as self-driving vehicles, assembly lines, assisted surgery, and autopilot in next-generation aircraft. The present study measured TIA alongside dispositional (Propensity to Trust machines; PTT) trust and situational (task difficulty) factors believed to impact TIA. People completed a conjunction visual search task with and without the help of an automated system and made subjective assessments of task difficulty after each trial. TIA and PTT machines were assessed at the beginning of the study, and TIA was assessed again at the end. Findings indicated a significant decrease in TIA scores over time and a significant positive relationship between peoples’ PTT machines and average TIA scores. However, PTT machines did not affect pre- or post-experiment TIA differently. Additionally, our findings did not provide support for a relationship between subjective assessments of task difficulty and TIA, likely due to the aggregate nature of these measurements. These results confirm that performing a task with an automated system allows for the development of learned trust and that PTT machines is an important dispositional factor affecting TIA. These findings increase our understanding of how dispositional, situational, and learned factors affect TIA when captured together. These findings also underscore the importance of studying these factors simultaneously, as this is how trust is built and shifted in real-world environments.