A paperless environment for annotating student assignments is appealing to teachers and students. However, to do this, while retaining the richness and ease of annotating the work with a red pen, has not been possible until recently. This project presents an annotation problem that requires digital annotation, and additionally functionality to properly support the user requirements to move ... [Show full abstract] efficiently between assignments, and simultaneously annotate and record marks for the assignment. With Penmarked, our prototype system, the teacher is able to annotate a digital document with a stylus and at the same time write scores which are recognized and saved into both the student's document and a standard file format. The evaluation suggests that Penmarked is a viable alternative to both paper and existing paperless environments.