This chapter explores the use of contractual tools by trust parties. Trust parties have perceived three types of risk in the creation and ongoing management of charitable trusts: the vagueness of the law, public scrutiny, and regulatory scrutiny. These risks motivate trust parties to use contract clauses to re-adjust the legislative framework of charitable trusts, and two levels of relationship are accordingly regulated in this practice. The chapter first analyses the horizontal relationship between settlors and trustees. Based on a review of the charitable trust contracts collected, insights are offered into the common contractual arrangements and how trust parties use these arrangements to reallocate their powers and duties. The chapter then examines the hierarchical relationship between regulators and trust parties. It is found that regulators are disposed to guide the use of contract tools between trust parties. This approach entitles regulators to tightly control the use of charitable trusts so as to advance the state’s public welfare goals to the largest extent.