In recent years, online fundraising (e-philanthropy) has grown to become a critical component of charitable fundraising in the Western world. The rapid development and proliferation of e-philanthropy means the need to critically investigate digital spaces as distinct communicative entities has now become necessary. Research in the field has revealed that digital documents differ from their hardcopy equivalents in terms of how they are consumed, since readers’ expectations vary when reading online vs. offline documents. The following research paper explores the direct mail fundraising letters and email appeal campaigns of three non-profit organizations operating in Toronto, Canada. Using Karen A. Schriver’s model for Document Design and Vijay Bhatia and Thomas A. Upton’s seven-move discourse structure for the direct mail letter genre, the goal of this MRP is to compare and contrast the traditional direct mail letter to its digital counterpart in order to identify the differences between the written rhetorical and visual document design strategy applied to each medium. A comparison between the printed and digital formats of the direct mail letters will hopefully provide a better understanding of how the traditional direct mail fundraising letter should be tailored for successful online consumption.