The practical operationalisation of resilience within cities is strongly linked to technology, such as better construction materials or redesigning urban form. Institutional and private sector actors often focus on issues relating to the technological innovation journey, such as ‘pathways’ to implementation or ‘barriers’ to market uptake, rather than whether adaptive technologies are the most appropriate resilience solution. These discourses frame urban resilience from the perspective of an innovation journey where technologies are perceived to succeed if there is high uptake. However, given the multi-perspective and multi-scale nature of urban resilience, the idea of ‘success’ inevitably has complex spatial, temporal and scalar dimensions. The paper uses the case of property level flood resilience (PFR) technologies in the United Kingdom to introduce the notion of ‘contingent resilience’ as a means to understand the trade-offs that are part of assessing and evaluating climate resilient technologies. We reveal that there are fundamental contradictions in what is deemed as a ‘success’ depending on who is framing the problem, when the judgement is made, or where the scale of analysis lies. Above all, the paper highlights the importance of illuminating the struggles that do not just define success, but that spatially and temporally redistribute climate resilience in a hidden manner.