Checklists play a crucial role in flight safety. However, designing checklists that are suitable for addressing the challenging nature of real-world activities is difficult. The traditional design of aviation checklists faces challenges since the support needs of pilots are constantly evolving in response to the increasing complexity of situations resulting from the use of more sophisticated technologies in aircraft. When the design of checklists does not support pilot activities adequately, the consequences can be devastating. In this study, the layout of such a checklist system was explored as a mechanism for supporting the pilot in dealing with challenging situations. The results of this research suggest that to improve the ability of checklists to support pilots, merely translating a paper Quick Reference Handbook (QRH) into a digital format is insufficient. The base layout, i.e., the layout design that was most like the traditional paper checklist, impeded the pilot’s activity, while the side-by-side and tabbed layouts each provided certain advantages to pilots in dealing with the scenario in this study. The side-by-side layout required fewer interruptions to refer to other resources when completing tasks, offered the pilot flexibility to choose how to progress through the checklists, and provided enhanced visibility of resources where needed. However, this layout was limited in the number of checklists that it could handle simultaneously. The tabbed layout provided shortcuts to checklists and resources during use but was limited by the loss of visibility of checklist content during navigation.