This paper deals with the educational necessity of collaborative learning and individual assessment. Historically,communication-based inefficiencies in student collaboration supported individual assessment but increasingly content creation technologies are both overcoming these inefficiencies and enabling students to collaborate during assessments. The rapid proliferation in the adoption of Generative AI packages such as ChatGPTis accelerating these challenges faster than universities can respond. This paper presents five, scaffolding assessment designs that are currently being piloted within graduate and undergraduate university classes. Crucially each strategy is predicated on the readily achievable -if scary -notion that authentic assessment and Generative AI services can be frenemies. Strategies covering extension across a range of quantitative and qualitative classes are detailed. Preliminary findings and 'next steps' are presented.