In this chapter Morton, a secondary history teacher in Vancouver, describes his involvement with The Benchmarks of Historical Thinking project. The project is described by Morton as a program that reforms history teaching with professional development and the creation of assessment tools and new curriculum. Morton not only reformed his own history classes with the program but was also a “lead teacher” for the program. This chapter traces not only Morton’s passing through the program’s “zones of uncertainty” by also the concerns of teachers from across Canada. Morton highlights the difficulties with teaching as a profession and the added difficulties and barriers faced by teachers seeking to introduce new theories and modes of assessment into the classroom. It is a challenge for teachers to change their practice: it does not happen immediately. The rest of the chapter traces Morton’s triumphs and tribulations with using the program with his history class in their creation of WWI films, using historical footage, for Remembrance Day. He then uses case studies of teachers from across Canada who have introduced the program into their own teaching. In conclusion, the program has the potential to aid students in thinking historically; however, there needs to be time and support provided for teachers.