Advice can be used for purposes other than help with practical reasoning, some of which strain trust within an advice relationship. This chapter examines ethical expectations of advisors and advisees that go beyond the norms of advice. Two cases are presented in which advice is sought for strategic purposes, to reduce the advisee’s exposure to blame or criticism. Next, a case of strategic advising is examined, in which advice serves as a poor substitute for the practical help that an advisor owes. The implications of strategic deployments of advising for trust within advice relationships are drawn out, and then a different threat is introduced: advisor over-identification with an advisee’s practical project. Eric Wiland’s reading of a controversial legal case serves as a basis for exploring the limits of advice as a form of help. The chapter concludes with a discussion of the relational dynamics of helping relationships.