We live in truly volatile and insecure times, defined by for example, enhanced climate and other environmental change, and major political and governance changes across the globe. Conditions are not always optimal for long-term and sustainable urban forestry. This presentation looks at how urban forestry in different cities and countries perform under increasing pressures. It draws lessons from situations where it faced major challenges, ranging from drastic cutting of government support in Ontario, Canada, to the increases in pests and diseases facing large parts of the urban forest. It also identifies cases where opportunities have emerged, such as the launching of China’s national Forest City program and the global trend of cities implementing so-called ‘nature-based solutions’. Specific focus will be on how the individual urban forester is impacted by this climate of change and how they are able to be successful.