Gifted mathematicians often struggle to remain motivated when pursuing higher-level study, yet Further Education institutions rarely offer effective tailored support, prioritising lower-attaining learners. Having identified Vygotskian social learning as a potentially suitable theory for aiding motivational pedagogical-design, two gifted students attended four problem-solving sessions devised to trial five scaffolding techniques: modelling, collaboration, questioning, hints and independence. Semistructured diaries were developed to help them contribute detailed insights, seeking to better understand how the techniques influenced their ability to make progress with advanced mathematical problems, and hence to refine Vygotsky's theory of Zones of Proximal Development for this purpose. Both participants described similar tipping-points between motivation and frustration. My influence as a 'more knowledgeable other' both supported and hindered their navigation of this knife-edge depending on the situation and strategy utilised, leading to recommendations for effective scaffolding.