A UCSF researcher discovered that traditional transcripts poorly predict student success in real-world research settings, leading him to develop AI tutors called Gems that refuse to provide direct answers and instead engage students in challenging conversations designed to build durable learning through productive struggle. The article explores how this approach to assessment and learning mirrors broader higher education questions about measuring what students actually know versus what they can look up. Instructure’s Canvas platform is positioned as supporting these new assessment paradigms.