This workshop explores web annotation as a core digital pedagogical practice for the 21st century classroom. This emergent technology allows Internet users to privately comment on or publicly discuss any web page. It can be applied to teach students traditional literacy skills like close reading but also newer forms of digital and media literacy. But web annotation can also be leveraged to in text mining and other digital humanities projects. Workshop participants will be introduced to the pedagogical value of web annotation and gain hands-on experience with an open-source, standards-based annotation client, Hypothes.is. Attendees will leave with a solid orientation in the basic functionality of web annotation as well as specific collaborative annotation exercises and projects that can be used in their classrooms.