Generative AI has the potential to unlock once-in-a-generation efficiency gains for enterprises across all industries, but traditional IT outsourcing contracts do not yet account for these gains. As enterprise decision makers become increasingly aware of GenAI’s potential, there is a growing call to renegotiate IT outsourcing contracts. This article guides enterprise decision makers to assess the value at stake from existing IT outsourcing contracts considering productivity gains offered by GenAI. The authors provide guidance for MSPs on how to best support enterprises to fill GenAI capability gaps while rapidly gaining market experience and recognition.