Objective: We investigated how people used cues to make Judgments of Difficulty (JODs) while observing automation perform a task and when performing this task themselves. Background: Task difficulty is a factor affecting trust in automation; however, no research has explored how individuals make JODs when watching automation or whether these judgments are similar to or different from those made while watching humans. Lastly, it is unclear how cue use when observing automation differs as a function of experience. Method: The study involved a visual search task. Some participants performed the task first, then watched automation complete it. Others watched and then performed, and a third group alternated between performing and watching. After each trial, participants made a JOD by indicating if the task was easier or harder than before. Task difficulty randomly changed every five trials. Results: A Bayesian regression suggested that cue use is similar to and different from cue use while observing humans. For central cues, support for the UAH was bounded by experience: those who performed the task first underweighted central cues when making JODs, relative to their counterparts in a previous study involving humans. For peripheral cues, support for the MEH was unequivocal and participants weighted cues similarly across observation sources. Conclusion: People weighted cues similar to and different from when they watched automation perform a task relative to when they watched humans, supporting the Media Equation and Unique Agent Hypotheses. Application: This study adds to a growing understanding of judgments in human-human and human-automation interactions. © 2024 Human Factors and Ergonomics Society.