Pupil size is known to correlate with the changes of cognitive task workloads, but how the pupil responds to requirements of basic goal-directed motor tasks involved in human-machine interactions is not yet clear. This work conducted a user study to investigate the pupil dilations during aiming in a tele-operation setting, with the purpose of better understanding how the changes in task requirements are reflected by the changes of pupil size. The task requirements, managed by Fitts' index of difficulty (ID), i.e. the size and distance apart of the targets, were varied between tasks, and pupil responses to different task IDs were recorded. The results showed that pupil diameter can be employed as an indicator of task requirements in goal-directed movements-higher task difficulty evoked higher valley to peak pupil dilation, and the peak pupil dilation occurred after a longer delay. These findings contribute to the foundation for developing methods to objectively evaluate interactive task requirements using pupil parameters during goal-directed movements in HCI.