This chapter reviews continuing usability problems with hypertext and Web applications and highlights new issues, in particular, cultural and ethical, brought about due to internationalisation. It argues for a move away from treatment to prevention, from treating the end-user’s symptoms — themselves a reaction to bad design — to avoiding the bad design. Therefore, the way hypertexts and the Web are designed and built needs to be re-examined. It suggests that new approaches to Web modelling are required to address usability issues that might be due to human errors or design problems. This chapter concludes by suggesting several practical and theoretical contributions to address the deficiencies in current hypertext and Web design.