A poorly designed riverfront intervention typically fails on several levels: a bad program, with the wrong budget and timing, no concern for local needs or context, results in an unattractive and costly intervention, with reduced to no social or environmental benefit. Urban riverfront interventions may be improved in the future if, when deciding what to do with our urban riverfronts, we learn from past mistakes. This may be as important (or perhaps more) as observing what worked. The successful element in another city may not be repeatable, as the context and opportunity was very specific to that one city. Yet, recognizing what didn’t work elsewhere, the causes for failure, may provide us with the clues we need on how to improve our own projects. Knowing how to avoid oversizing, overspending, inadequately planning, failing to attract diverse publics and uses or fail to provide ecological benefits will, paradoxically, provide us with an excellent framework on how to create a better, successful, intervention. To get it right, we should acknowledge the local context, the morphology of the river valley, the time and budget a set of solutions entail, and select uses and functions that work for a diverse crowd and provide multiple benefits, including good flood management performance and the restoration of the rivers’ natural connectivity.