The narrative of Lady Anne Clifford's marriage to Richard Sackville, later Earl of Dorset, has remained unquestioned in discussions concerning Clifford's legal disputes with her uncle Francis Clifford, fourth Earl of Cumberland over the inheritance of the Clifford land holdings in Westmorland and North Yorkshire. However, Anne Clifford's marriage was a vitally important component in the strategy for securing these lands for her. Margaret Russell, the Countess of Cumberland and Anne Clifford's mother, understood that in order to outmanoeuvre successfully Francis Clifford, and his powerful ally Robert Cecil, she would need an equally powerful ally who would champion Anne Clifford's claims to the Clifford estates. Russell thus entered into negotiations with several possible candidates including William Cecil, Lord Roos and Robert Carr, later Earl of Somerset. Even Anne Clifford's eventual marriage with Richard Sackville was complicated by concerns related to her inheritance dispute - its validity only confirmed nine months after it had taken place. This paper explores the motivations and strategies employed in the marrying of Anne Clifford and considers the way in which these negotiations both conformed to contemporary practice and yet were affected by the particular goals of Margaret Russell and Anne Clifford.