Wireless sensor networks in the past decade have become prevalent in areas such as environmental monitoring, hazard detection, and industrial IoT applications. Current research focuses on improving the energy efficiency, throughput, robustness, and resilience of such networks. Within this work, failures are rarely held up as something to be explored and discussed, as improvements and novelty are the traditionally highlighted outcomes. However, in order to undertake effective research, highlighting failures can help mitigate against them occurring in the future. In this paper, we wish to highlight failures in our work, times when engineering and social challenges were barriers to the completion of world class research. Three stakeholder driven case studies from the London Living Lab are chosen namely air quality, microclimate and urban bat monitoring. From these deployments, challenges are highlighted and the subsequent methods developed to overcome said challenges are explored with the view that future work may benefit from the outcomes of these experiences.