Based on the Quadruple Bottom Line of design for sustainability, we recently introduced the concept of ‘Cyber-Sustainability’ as a means of discussing the degree to which the current trajectory of Web-mediated technologies may not be sustainable with respect to environmental, social, spiritual, and secondarily economic human needs. This paper introduces, as an additional concern, society’s increased dependence on digitisation, which decreases society’s resilience in the face of possible localised or systemic disruptions to Web services. Given that technological progress is often envisaged as a future in which daily life is characterised by greater dependence on technology, this paper seeks to understand how this seemingly unsustainable trend is fostered by powerful associations between the notion of ‘progress’ and Post-Industrial conceptions of ‘meaning’. To determine how this specific understanding of progress has underpinned the current trajectory of technological development, we analyse Progress as a frame that encompasses a set of values, shown here to be in tension with environmental, social and spiritual sustainability. Finally, an alternative ambition for a sustainable digital future is offered in the form of a new positive development frame, within which specific Cyber-Sustainable design criteria might be generated.