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Abstract
A key project in mainstream epistemology investigates the sense in which beliefs are vulnerable to knowledge-undermining luck and/or risk. This chapter will explore a related but largely overlooked question of how and to what extent our grasping connections between propositions is vulnerable to understanding- undermining luck and risk. The result will be a better view of how our attempts to understand the world are vulnerable when they are, and how to better mitigate against such vulnerabilities.