This Presentation was for the Orphans’ Court Judges as part of the Judicial College addressing the various rules of construction to be applied when interpreting Wills. The starting point is the “plain meaning” rule which purports to restrict understanding a decedent’s Will to the “four corners” of the Will. The plain meaning rule, however, never literally prohibited recourse to extrinsic evidence. Perhaps the most expansive exception to the rule is the surrounding circumstances exception. This exception permits the Court to consider extrinsic evidence of the circumstances surrounding the testator which, in its nature and effect, simply explains what the testator has written. This Presentation describes how Wills are to be interpreted by Maryland courts.