Although the need for good management and maintenance of open spaces should be an obvious concern, society’s awareness of the need for place-keeping is not common in most countries. Even less common is concern for evaluation of place-keeping. There is generally no requirement to conduct an evaluation of a place (post-place-making) once it has been created or regenerated, other than those linked to funding bodies, which do not tend to seek evaluation over the long term. Moreover, there is little understanding of the relevance of evaluation of place-keeping within a more holistic approach to long-term management. In order to explore how this can be overcome, we need to know how place-keeping has been evaluated to date and what issues arise from existing and innovative approaches. This chapter therefore looks at some examples of place-keeping and attempts to learn from them, and explores how this contributes to an effective place-keeping approach.