Law plays only a peripheral role in L.M. Montgomery’s fiction. Lawyers occasionally appear as supporting characters and the odd plot point turns on a legal document such as a will. But when conflict surfaces in Montgomery’s fictional communities, her characters rarely turn to law either as a means of dispute resolution or as a force to punish transgressions. Initiating legal action, even to assert admitted rights, is generally frowned upon within these communities. Disputes between individual characters and between and among families are ideally resolved within the community without resort to lawyers or courts. Montgomery was not able to sidestep legal conflict in her life in similar fashion. In her professional life, she endured a series of lawsuits against her first U.S. publisher L.C. Page that began in 1917 and extended for over ten years. A lawsuit also dominated her personal life between 1921 and 1923, and continued to preoccupy her for several years thereafter. This was a suit brought by a neighbour, Marshall Pickering, against Montgomery’s husband Ewan Macdonald following a 1921 car accident. Montgomery experienced the accident, served as a witness in the trial that followed, and wrote about it at length in her journal. In this paper, I explore the contrast between the role that legal conflict played in Montgomery’s life and in her fiction.