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As professional users interact with more AI-enabled tools, it has become increasingly important to understand how their work and behaviour are affected by such tools. In this paper, we present the insights that we have gleaned from a qualitative user study conducted with nine of our software’s users who are all legal professionals. We find that as our participants become more accustomed to the system they begin to subtly alter their behaviours and interactions with the system. Using their shared experiences, we distill these into insights that may inform the design of similar systems.