Hope is an attitude with a distinctive epistemological dimension: it is incompatible with knowledge. This chapter examines hope as it relates to knowledge but also to probability and inductive considerations. Such epistemic constraints can make hope either impossible, or, when hope remains possible, they affect how one’s epistemic situation can make hope rational rather than irrational. Such issues are especially relevant to when hopefulness may permissibly figure in practical deliberation over a course of action. So I consider cases of second-order (...) inductive reflection on when one should, or should not, hope for an outcome with which one has a long record of experience: in other words, what is the epistemology behind when one should, if ever, stop hoping for outcomes which have failed one many times in the past? (shrink)