On coming down from Oxford she lectured on Law at the University College of Wales, Aberystwyth. Having been called to the Bar in 1966, she joined the Chancery bar and practised as a Barrister for several years in Lincoln’s Inn, specialising in property and tax law. She later joined Lloyds Bank, where she specialised in international tax planning and became a senior executive in the trust department. It was at this time that she started to write. Fellow barrister John Tackebury praised her accomplishments at the bar: "As a woman, she had to have had a first-class mind to join the Chancery bar, to have built up a successful practice and to have become a senior executive at Lloyds, All these institutions were highly resistant to women at a senior level, and certainly to a woman who smoked a pipe."
She was a lifelong pipe-smoker, and inveterate crossword solver, reaching the final of The Times Crossword Competition more than once. For many years, she lived in Barnes, London, with her mother and aunt. She died of cancer in January 2000 in London, England.
Writing
Hilary Tamar series
This series of four books, described as "legal whodunits", were written over a period of twenty years. Their primary setting is the top floor of 62 New Square at Lincoln's Inn, where four young junior barristers have their chambers: Michael Cantrip, Desmond Ragwort, Selena Jardine and Timothy Shepherd. While the last named only appears sporadically, taxes barrister Julia Larwood, who works in the adjacent premises, is a regular visitor and is in effect the fourth member of the group. These characters are in some ways thinly drawn, never communicating in anything other than an ironic tone, so that even when they are in deadly danger the atmosphere remains uniformly light-hearted. Acting as a kind of parent to the group is the first-person narrator, Professor Hilary Tamar. Professor Tamar, a former tutor of Timothy Shepherd, also acts as the main detective, although other characters make contributions to the eventual solutions. Professor Tamar is frequently physically removed from the action and is kept informed by a series of improbably long letters and telexes. This distancing is amplified by Caudwell's strategy of not specifying Tamar's sex and never specifying the reason for the strong bond which the character enjoys with the young advocates. The plots are intricate, carefully realised, and strongly tied to the locations chosen, these being Venice, Corfu, Sark and an English village. The author’s expertise in tax law is frequently brought into play, inheritance law being relevant to financial motives for murder. She was particularly popular among other legal professionals, including American jurist Robert Bork, who was once quoted as saying, "In my opinion, there can't be too many Sarah Caudwell novels".
Other writing
Caudwell collaborated on crime short stories with Michael Z. Lewin and with Lawrence Block for The Perfect Murder. She also wrote a play, The Madman’s Advocate, which was given a rehearsed reading in Nottingham in 1995: a study of Daniel M'Naghten's attempt in 1843 to assassinate Sir Robert Peel and the resulting establishment of the M'Naghten Rule as a legal standard for defining the sanity of a defendant in law.