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 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.