Recently, it has been debated as to whether understanding is a species of explanatory knowledge. Those who deny this claim frequently argue that understanding, unlike knowledge, can be lucky. In this paper I argue that current arguments do not support this alleged compatibility between understanding and epistemic luck. First, I argue that understanding requires reliable explanatory evaluation, yet the putative examples of lucky understanding underspecify the extent to which subjects possess this ability. In the course of defending this claim, I also provide a new account of the kind of ‘grasping’ taken to be central to understanding. Second, I show that putative examples of lucky understanding unwittingly deploy a kind of luck that is compatible with knowledge. Finally, appealing to a number of works on explanation and its attendant epistemology, I argue that alleged instances of lucky understanding that overcome these two obstacles will invariably violate certain norms of explanatory inquiry – our paradigmatic understanding-oriented practice. By contrast, knowledge of the same information is immune to these criticisms. Consequently, if understanding is environmentally lucky, it is always inferior to the understanding that a corresponding case of knowledge would provide.