The contemporary urban water system is under extreme pressure due to growing demand, climate change, and social inequality. Conventional methods to mitigating extreme water events have proven to be insuicient to safeguard our growing urban centers. Unless the competing demands and pressures of the urban water system are addressed in holistic manners, we will soon lack of access to good-quality water, and extreme water events will increasingly afect our metropoles, with most severe consequences for communities already living in marginal conditions. This chapter takes as point of departure that the future urban waterscape is a wicked problem in which actions taken to mitigate the problems are often inadequate and temporary, even when they are the result of the public debate and shared concern. The current urban water system has reached a critical threshold, but how can innovative urban water design or planning solutions be implemented when there is so much at stake? The chapter will address the urban waterscape, its contemporary challenges and what we can expect in future climate conditions. Furthermore, we will discuss contemporary solutions as well as highlight the sociopolitical, economic, and ecological barriers to their implementation. To illustrate the challenges as well as the range of solutions, we will present the algal blooms in Lake Erie, USA, as a case study. We will end with an elaboration on how to innovate in the case of wicked problems.