This thesis examines the challenges of hypertext writers with respect to six aspects of writing: authority, audience, organization, document design, style and multimedia use. This study is primarily based on the theories presented in the three books-Jay David Bolter's Writing Space, George P. Landow's Hypertext 2.0 and Ilana Snyder's Hypertext. Information is collected by means of structured interviews from Bolter and Snyder. This study reveals that the hypertext medium does pose challenges to writers who are used to writing for the print medium and are new to the hypertext medium. Hypertext environment requires that the writer should either possess multiple, diverse skills or work collaboratively. Primary causes of challenges are newness of the medium and lack of education emphasizing visual literacy. Moreover, the challenges point towards the necessity of a new kind of literacy that includes not only visual literacy, but also multimedia literacy. A new rhetoric that addresses both a document's visual design and structural design is very necessary.