In this article, the author shares challenges of teaching writing in a virtual classroom. One of the challenges of online education--the often-asynchronous nature--also holds one of the strengths: the opportunity for a lesson to continue long after the classroom closes. The author's experiences online offer ways to rethink meanings of youth writing and engagement in "nontraditional" contexts. Writing teachers must hold on to what they know works while embracing creativity. Writing teachers must give students the time, space, and opportunity to investigate how they can gain personal connections to texts in ways that support their writing.