‘Anxious Artefacts’ addresses Richard Brautigan’s poem: “All Watched Over by Machines of Loving Grace” by designing a set of systems that aim to quantify how an artefact can cause anxiety in a person. Artefacts have potential anxious properties; the set of systems uses quantitative methodologies to examine those properties and allows us to identify how close we are to achieving mutually programming harmony. Brautigan is a technological utopian and ‘Anxious Artefacts’ brings awareness to barriers that stop us from reaching his dream, a dream that he wanted everyone to share, one where we can all be watched over by machines of loving grace. ‘Anxious Artefacts’ does not only look at the causes but the alleviations of anxiety to understand that there is a scale of severity and an element of condition each artefact has to have in order to carry out a cause or an alleviation. This projects hopes to help discover a profound understanding of our anxieties.