From a Self-Determination Theory perspective, children are expected to grow according to innate tendencies in supportive environments, such as nature-based educational settings. The role of the practitioner is generally viewed as facilitative in these contexts. We report findings from a qualitative study with a sample of 18 UK-based outdoor educational practitioners. We asked them to respond to four hypothetical situations with differing levels of required intervention. Our purpose was to examine the extent of autonomy support and structure that they would hypothetically provide to the children in each of these different scenarios, and even uncover possible tensions in the application of autonomy support and structure. Our analysis suggests that, in situations of low interventional requirement, practitioners could understate structure and autonomy support and, in situations of high interventional requirement, prioritize structure over autonomy support. The challenge for practitioners that was revealed in this research, as well its implications, are discussed.