Surrogate's Courts rely on heavily interested party testimony to adjudicate trusts and estates contests. Determining what the testator's intent was lies at the heart of many disputes, and often invokes competing stories, vague, incomplete documentary evidence, and parties with conflicting interests. We address the most common evidentiary obstacles trusts and estates litigators should be aware of, including: (1) the probate exception to the attorney-client privilege; (2) how to invoke the Three-Two Year Rule; and (3) the Dead Man's statute.