Giving money away well is harder than it sounds, and the tax code makes it harder by conditioning every benefit on a set of formalities that donors routinely discover too late. This article explains how charitable gifts actually get structured: the deduction and its percentage limits, the substantiation rules that void an otherwise valid deduction over a missing sentence in a receipt, the appraisal requirements for noncash property, and the vehicles — donor-advised funds, private foundations, charitable remainder and lead trusts, and qualified charitable distributions from retirement accounts — that serve different objectives and carry different burdens. It covers the private foundation excise tax regime that most donors have never heard of, the restrictions that follow a restricted gift for decades, and what happens when a charity cannot use a gift as the donor directed. Two donors are followed from intention to execution.