In this paper we report on new challenges when teaching UX students how to sketch and prototype their designs. We argue that UX students sketch and prototype differently than other design students, and we discuss how changes in the field necessitate a response in education. We describe sketching and prototyping as a continuum that students successfully traverse when they follow a process of ‘double loop learning’. We highlight three new challenges: (1) New computational design materials, (2) new maker tools, and (3) changes within the tech industry. We explore these three challenges through examples from our students, and we outline strategies for sketching and prototyping in this new reality. We conclude that this is a starting point for further work on keeping education up to speed with practice.