The digital environment has had an immense effect on American society, learning, and education: we have more sources available at our fingertips than any previous generation. Teaching and learning with these new sources, however, has been a challenging transition. Students are confronted with an ocean of digital objects and need skills to navigate the World Wide Web and numerous proprietary databases. Writing and disciplinary habits of mind are more important than ever in this environment, so how do we teach these in the digital age? This paper examines the current digital environment that humanities faculty face in their teaching and explores new tools that might support collaborative writing and digital skills development for students. In particular, this paper considers the effectiveness of a specially configured multi-agent wiki system for writing in a large lecture humanities course and explores the results of its deployment over two years.