HAWK (Help Agent for Writing Knowledge) is a new instructional software for the essentials of writing that runs on tablets. In trials with an after-school K-12 subject group, the use of the software showed improved writing capabilities of most students. One of the activities supported by the software involves students drawing letter shapes by tracing paths through scaffolded channels. Additionally, we detail the design studies we performed prior to implementing the full software package. We focused on how software can provide graphical feedback to students in the context of a stylus and touch-based interface for the basic educational activity of learning to write letters of the alphabet.