In response to the need to mitigate urban heat risks, green infrastructure enhancements have been widely advocated in recent times. To meet the challenges of implementing enhancements in dense cities, surface greening approaches such as vertical living walls have gained increased prominence. This paper reports on the principal challenges and drivers influencing the sustainable maintenance of such installations, identified through the inspection of ten European case studies and interviews with their management authorities. The study reports on key maintenance areas highlighted by installation managers as requiring attention. Furthermore, it reports on human engagement behavioural aspects as being a significant motivator, with installation managers assigning value to building occupant and public perception of an installation’s flourishing state. The evidence reported, therefore, is beneficial to key decision-makers and designers when considering the inclusion and sustainable maintenance of such greening installations.