This study explored critical incidents that occurred for students completing a web development project using multiple digital tools. It found that students encountered the most issues with tasks related to presentation development, seeking information across different search tools, and working between separate websites. Qualitative analysis revealed themes around developing presentation structures, information seeking strategies, working across sites, dealing with social/environmental challenges, and the impact of prior skills. The study suggests understanding student technology experience and abilities to transfer skills is key, as is instruction in organizing information for effective sourcing. Next steps include further examining the impact of experience and search tool variation, and defining the role of complexity in online presentation.