In this chapter the authors look at a pilot test of the Sourcer's Apprentice software developed to support primary source investigation.  Underlying the development of the software is a belief that history provides a rich textual environment that, if supported, can improve students’ literacy and critical thinking skills.  Using a Documents Model as an analytic tool for creating a structure to read and understand multiple texts would accentuate a Causal-Temporal Event Structure in a ‘situations model’ and an intertext predicate that enables document-to-content links.  The computer program Sourcer’s Apprentice was created to support this model and is subsequently based on students solving problems and receiving immediate feedback on their use of texts throughout their investigation.