One way of characterizing what makes someone a good reasoner is to appeal to intellectual virtues, such as curiosity, fair-mindedness, or epistemic humility. My aim in this paper is to show that explaining how the virtue of humility should manifest itself in complex reasoning is more difficult than one might think. A very natural view of what intellectually humble deliberation looks like is problematic, because it leads to an infinite regress. I will explore whether and in which way this regress is vicious, and how our answers to these questions can lead us to a better account of how humility can inform stopping rules for good reasoning.