In 1998 a massive gold signet ring was found by metal detecting in the parish of Raglan, Monmouthshire (Gwent), close to Raglan Castle. Now generally known as the Raglan ring, it is a remarkable example of late medieval goldsmiths’ work. This paper considers its motifs, legend, date and stylistic affinities. Its findspot is close to the castle-building programme at Raglan continued by William Herbert (executed 1469), who projected his position as premier supporter of the House of York in a variety of ways. Possible ownership is discussed, as is its wider context (including newly discovered signet rings from Wales).