One main design current, User experience design dominates the research landscape of user interface design. Usability has been asserted as the success criteria of our online environment. Maximising the speed and ease of use augments our user experience, it makes us feel empowered, while subjecting us to a process of quantification, profiling and restriction. UX design appears to be a framework of tracking procedures which analyse the users behaviour, but their proclaimed ambition of accessibility is hard to distinguish from implicit strategies of tech-business models.The web is becoming a large scale experiment where every action we make is considered and used to monitor our online behaviour. The research is based on a deconstruction of usability tools through a variety of sources. Starting with an analytical reading of blogs and UX design forums, in order to understand the current ins-and-outs of this practice. Coupled with a more in-depth analysis of manifest documents determining the origins and evolution of this particular research area. This is followed by a personal analysis of technicals details which allowed me to identify the direct modifications occurring in my daily environment. And finally concluding with a historical analysis of interface theories leading me to consider alternatives to the current foundation. This thesis contains a collection of essays and interviews that investigate the design processes of user-friendliness. It questions what being a user is, and what, how, and who define the user’s agency in today’s web environment. It reflects on two principal notions, that of ability and usability. All leading to a discussion of the designers position within this paradox, where usability gained comes at the cost of agency and autonomy.