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This chapter considers how trust affects performance in free improvisation and questions whether aesthetic evaluation is relevant in the music performed. It investigates the reasons why improvisers trust the evolving generative nature of their improvisation, in a completely spontaneous “only that moment counts” approach, and considers how both personal and collective expectations and expertise shape this trust. The chapter links to the earlier discussion on aspiration by proposing that the evaluation of free improvisation primarily hinges on whether what has been created aligns with what the musician intended, given that intentions were clear in the first place. It considers the relationship between creative intent and outcome, concluding that, ultimately, the trust a musician has in improvisational practices is built on the trust they have in themselves as musicians and as individuals.