While subjective judgment is recognized by the health professions education literature as important to assessment, it remains difficult to carve out a formally recognized role in assessment practices for personal experiences, gestalts, and gut feelings. Assessment tends to rely on documentary artefacts—like the forms, standards, and policies brought in under competency-based medical education, for example—to support accountability and fairness. But judgment is often tacit in nature and can be more challenging to surface in explicit (and particularly written) form. What is needed is a nuanced approach to the incorporation of judgment in assessment such that it is neither in danger of being suppressed by an overly rigorous insistence on documentation nor uncritically sanctioned by the defense that it resides in a black box and that we must simply trust the expertise of assessors. The concept of entrustment represents an attempt to effect such a balance within current competency frameworks by surfacing judgments about the degree of supervision learners need to care safely for patients. While there is relatively little published data about its implementation as yet, one readily manifest variation in the uptake of entrustment relates to the distinction between ad hoc and summative forms. The ways in which these forms are languaged, together with their intended purposes and guidelines for their use, point to directions for more focused empirical inquiry that can inform current and future uptake of entrustment in competency-based medical education and the responsible and meaningful inclusion of judgment in assessment more generally.