The focus of this chapter is Web accessibility for disabled people, given that much of the Web remains inaccessible or difficult to access. The topic of disabled people’s Web access is introduced through a consideration of disability discrimination legislation and a description of how the law applies to Web accessibility. There is a tension between the active burdens the legislation demands and the relative passivity of approaches towards disability discrimination that still prevail. This is exacerbated by the widespread acquiescence to automatic software checking. The history of the development of the World Wide Web in terms of accessibility is briefly described. This reveals the familiar tension between a ”free market” approach and regulation that does not readily support social inclusion through accessibility. A table of detailed points showing where automatic tools cannot perform an adequate check against the W3C standards is presented followed by a narrative expanding our claim for the poverty of automatic approaches.